The structure of molecule $\mathbf A$ is:

<MultiModal>![O=C(C#C)N(CC#CC#CCOC1=CC(C)=CC(C)=C1)C2=CC=CC=C2](/media/uploads/cbd08583-46c6-471d-a26a-a82536d98234.png)</MultiModal>

$\mathbf A$ first transforms into a highly reactive six-membered ring intermediate $\mathbf B$ at high temperature, then undergoes a reaction to form intermediate $\mathbf C$, and finally reacts with compound $\mathbf D$ to produce compound $\mathbf E$. It is known that all alkyne bonds participate in the reaction in the first step, and the subsequent two steps are both ene reactions.

The structure of compound $\mathbf D$ is:

<MultiModal>![O=C(C=C1)N(C2=CC=CC=C2)C1=O](/media/uploads/9b8ea5c5-ecde-4060-b009-e9d9de565fb5.png)</MultiModal>

Select the correct option regarding this reaction from the following choices.
分子$\mathbf A$的结构为：

<MultiModal>![O=C(C#C)N(CC#CC#CCOC1=CC(C)=CC(C)=C1)C2=CC=CC=C2](/media/uploads/cbd08583-46c6-471d-a26a-a82536d98234.png)</MultiModal>

$\mathbf A$在高温下首先转变为活性极高的六元环中间体$\mathbf B$，随后发生反应转变为中间体$\mathbf C$，最后与化合物$\mathbf D$发生反应生成化合物$\mathbf E$。已知第一步中所有炔键均参与了反应，后两步反应均为ene反应。

化合物$\mathbf D$的结构为：

<MultiModal>![O=C(C=C1)N(C2=CC=CC=C2)C1=O](/media/uploads/9b8ea5c5-ecde-4060-b009-e9d9de565fb5.png)</MultiModal>

选择下列选项中关于这个反应正确的一个选项。
The intermediate $\mathbf C$ contains four rings
Compound $\mathbf E$ contains three six-membered ring structures.
The compound $\mathbf E$ contains two carbonyl structures.
The intermediate $\mathbf C$ contains two methyl groups
The intermediate $\mathbf B$ contains two six-membered rings.
The intermediate $\mathbf B$ contains an oxygen atom with nucleophilicity stronger than that of the oxygen atom in diethyl ether.
There is a nitrogen atom in compound $\mathbf E$ with nucleophilicity stronger than that of the nitrogen atom in triethylamine.
The compound $\mathbf E$ undergoes hydrolysis in a strong alkaline solution, with the main products containing a phenyl group.
中间体$\mathbf C$包含四个环
化合物$\mathbf E$包含三个六元环结构
化合物$\mathbf E$包含两个羰基结构
中间体$\mathbf C$包含两个甲基
中间体$\mathbf B$包含两个六元环
中间体$\mathbf B$包含亲核性强于乙醚中氧原子的氧原子
化合物$\mathbf E$中存在亲核性强于三乙胺中氮原子的氮原子
化合物$\mathbf E$在强碱溶液中水解，主要产物包含一个苯基
At high temperatures, the alkyne bond exhibits diradical character, first undergoing a [4+2] cycloaddition reaction with a conjugated diyne. Thus, the structure of intermediate $\mathbf B$ is:

<MultiModal>![O=C1C2=CC(COC3=CC(C)=CC(C)=C3)=C=C=C2CN1C4=CC=CC=C4](/media/uploads/95698fc1-be4c-43a3-b705-9e7f2b4fb737.png)</MultiModal>
<Checkpoint>[[4+2] cycloaddition reaction between alkyne and conjugated diyne](1)</Checkpoint>

<Checkpoint>[O=C1C2=CC(COC3=CC(C)=CC(C)=C3)=C=C=C2CN1C4=CC=CC=C4](1)</Checkpoint>

Benzyne is highly reactive and undergoes an intramolecular ene reaction with a methyl-substituted benzene ring in a suitable position within the molecule, forming a new six-membered ring to yield intermediate $\mathbf C$. The structure of $\mathbf C$ is:

<MultiModal>![O=C1C2=CC3=C(C4C(OC3)=CC(C)=CC4=C)C=C2CN1C5=CC=CC=C5](/media/uploads/86e8ba8a-dd0e-4ed9-9ed1-e6788dd16425.png)</MultiModal>

<Checkpoint>[Ene reaction between benzyne and intramolecular methyl-substituted benzene ring to form a six-membered ring](1)</Checkpoint>

<Checkpoint>[O=C1C2=CC3=C(C4C(OC3)=CC(C)=CC4=C)C=C2CN1C5=CC=CC=C5](1)</Checkpoint>

The methyl-substituted benzene ring, whose aromaticity was disrupted during the ene reaction, tends to restore its aromaticity. Therefore, intermediate $\mathbf C$ undergoes another ene reaction with an alkene bond in another molecule to regain aromaticity. Thus, intermediate $\mathbf C$ reacts with $\mathbf D$ via an ene reaction to form product $\mathbf E$, whose structure is:

<MultiModal>![O=C1C2=CC3=C(C4=C(CC5CC(N(C6=CC=CC=C6)C5=O)=O)C=C(C)C=C4OC3)C=C2CN1C7=CC=CC=C7](/media/uploads/16cc079e-ff4f-4177-8905-5381297d53df.png)</MultiModal>

<Checkpoint>[Ene reaction between intermediate $\mathbf C$ and $\mathbf D$](1)</Checkpoint>

<Checkpoint>[O=C1C2=CC3=C(C4=C(CC5CC(N(C6=CC=CC=C6)C5=O)=O)C=C(C)C=C4OC3)C=C2CN1C7=CC=CC=C7](1)</Checkpoint>

Based on the deduced structures, options A through E can all be determined to be incorrect.

The oxygen atoms in intermediate $\mathbf B$ include carbonyl oxygen and aryl ether oxygen. The carbonyl oxygen requires one p orbital to form a π bond, so the lone pair occupies an orbital with lower p character and higher s character, resulting in lower energy and weaker nucleophilicity compared to the oxygen in diethyl ether. The aryl ether oxygen is conjugated with the aromatic ring, causing electron density to shift toward the ring and reducing electron density on the oxygen atom, making its nucleophilicity also weaker than that of diethyl ether oxygen. Thus, option F is incorrect.

<Checkpoint>[Oxygen atoms in intermediate $\mathbf B$ include carbonyl oxygen and aryl ether oxygen](1)</Checkpoint>

<Checkpoint>[The nucleophilicity of both carbonyl oxygen and aryl ether oxygen is weaker than that of diethyl ether oxygen](1)</Checkpoint>

The nitrogen atoms in compound $\mathbf E$ include amide nitrogen and imide nitrogen. Since both nitrogen atoms are conjugated with strongly electron-withdrawing carbonyl groups, their electron density decreases, resulting in nucleophilicity inferior to that of the nitrogen in triethylamine (which is bonded only to three alkyl groups). Thus, option G is incorrect.

<Checkpoint>[Nitrogen atoms in intermediate $\mathbf E$ include amide nitrogen and imide nitrogen](1)</Checkpoint>

<Checkpoint>[The nucleophilicity of both amide nitrogen and imide nitrogen is inferior to that of triethylamine nitrogen](1)</Checkpoint>

The product of complete hydrolysis of compound $\mathbf E$ is:

<MultiModal>![CC1=CC(CC(C(O)=O)CC(O)=O)=C(C(OC2)=C1)C3=C2C=C(C(O)=O)C(NC4=CC=CC=C4)=C3](/media/uploads/31ab35d3-61a2-4144-816e-2ce229e8954c.png)</MultiModal>

It contains only one phenyl group, so option H is correct.

<Checkpoint>[CC1=CC(CC(C(O)=O)CC(O)=O)=C(C(OC2)=C1)C3=C2C=C(C(O)=O)C(NC4=CC=CC=C4)=C3](1)</Checkpoint>
炔键在高温下体现双自由基性质，首先发生炔键和共轭二炔的[4+2]环加成反应，故中间体$\mathbf B$的结构为：

<MultiModal>![O=C1C2=CC(COC3=CC(C)=CC(C)=C3)=C=C=C2CN1C4=CC=CC=C4](/media/uploads/95698fc1-be4c-43a3-b705-9e7f2b4fb737.png)</MultiModal>
<Checkpoint>[炔键和共轭二炔的[4+2]环加成反应](1)</Checkpoint>

<Checkpoint>[O=C1C2=CC(COC3=CC(C)=CC(C)=C3)=C=C=C2CN1C4=CC=CC=C4](1)</Checkpoint>

苯炔具有高反应活性，与分子内处于合适位置的带甲基苯环发生分子内烯反应并形成新的六元环，生成中间体$\mathbf C$，$\mathbf C$的结构为：

<MultiModal>![O=C1C2=CC3=C(C4C(OC3)=CC(C)=CC4=C)C=C2CN1C5=CC=CC=C5](/media/uploads/86e8ba8a-dd0e-4ed9-9ed1-e6788dd16425.png)</MultiModal>

<Checkpoint>[苯炔与分子内带甲基苯环发生烯反应生成六元环](1)</Checkpoint>

<Checkpoint>[O=C1C2=CC3=C(C4C(OC3)=CC(C)=CC4=C)C=C2CN1C5=CC=CC=C5](1)</Checkpoint>

在烯反应中被破坏芳香性的带甲基苯环有恢复芳香性的倾向，因此中间体$\mathbf C$会与另一分子中的烯键再发生一次烯反应，恢复芳香性。因此中间体$\mathbf C$与$\mathbf D$发生烯反应生成产物$\mathbf E$，$\mathbf E$的结构为

<MultiModal>![O=C1C2=CC3=C(C4=C(CC5CC(N(C6=CC=CC=C6)C5=O)=O)C=C(C)C=C4OC3)C=C2CN1C7=CC=CC=C7](/media/uploads/16cc079e-ff4f-4177-8905-5381297d53df.png)</MultiModal>

<Checkpoint>[中间体$\mathbf C$与$\mathbf D$发生烯反应](1)</Checkpoint>

<Checkpoint>[O=C1C2=CC3=C(C4=C(CC5CC(N(C6=CC=CC=C6)C5=O)=O)C=C(C)C=C4OC3)C=C2CN1C7=CC=CC=C7](1)</Checkpoint>

根据上述推理出的结构可判断选项A到E均错误。

中间体$\mathbf B$中氧原子包括羰基氧原子和芳基醚氧原子。羰基氧原子需要1个p轨道形成π键，因此孤对电子占据轨道的p成分较低、s成分较高，能量较低，故亲核性弱于乙醚中的氧原子；芳基醚氧原子与芳环共轭，电子密度向芳环转移，氧原子上电子密度降低，亲核性也弱于乙醚中的氧原子，故F选项错误。

<Checkpoint>[中间体$\mathbf B$中氧原子包括羰基氧原子和芳基醚氧原子](1)</Checkpoint>

<Checkpoint>[羰基氧原子和芳基醚氧原子的亲核性均弱于乙醚中氧原子](1)</Checkpoint>

化合物$\mathbf E$中氮原子包括酰胺氮原子和酰亚胺氮原子，由于氮原子均与具有强共轭吸电子性质的羰基共轭，氮原子的电子云密度下降，导致两种氮原子的亲核性不如只连接三个烷基的三乙胺氮原子，故G选项错误。

<Checkpoint>[中间体$\mathbf E$中氮原子包括酰胺氮原子和酰亚胺氮原子](1)</Checkpoint>

<Checkpoint>[酰胺氮原子和酰亚胺氮原子的亲核性均不如三乙胺氮原子](1)</Checkpoint>

化合物$\mathbf E$完全水解的产物为：

<MultiModal>![CC1=CC(CC(C(O)=O)CC(O)=O)=C(C(OC2)=C1)C3=C2C=C(C(O)=O)C(NC4=CC=CC=C4)=C3](/media/uploads/31ab35d3-61a2-4144-816e-2ce229e8954c.png)</MultiModal>

只包含1个苯基，故H选项正确。

<Checkpoint>[CC1=CC(CC(C(O)=O)CC(O)=O)=C(C(OC2)=C1)C3=C2C=C(C(O)=O)C(NC4=CC=CC=C4)=C3](1)</Checkpoint>