2-benzoyl-3-(2-pyrrole)acrylonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-benzoyl-3-(2-pyrrole)acrylonitrile
• 英文别名: 2-benzoyl-3-(1H-pyrrol-2-yl)acrylonitrile；2-benzoyl-3-(1H-pyrrol-2-yl)prop-2-enenitrile
• 化学式: C₁₄H₁₀N₂O
• 分子量: 222.246
• InChiKey: TUKFFPXAFXRQFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl 2-(acetoxymethyl)buta-2,3-dienoate 、 2-benzoyl-3-(2-pyrrole)acrylonitrile 在 sodium carbonate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 12.08h， 以90%的产率得到benzyl (8R,8aR)-8-benzoyl-8-cyano-7,8a-dihydro-5H-cyclopenta[a]pyrrolizine-6-carboxylate
  参考文献：
  名称：

  Phosphine-Catalyzed Addition/Cycloaddition Domino Reactions of β′-Acetoxy Allenoate: Highly Stereoselective Access to 2-Oxabicyclo[3.3.1]nonane and Cyclopenta[a]pyrrolizine

  摘要：

  Two classes of phosphine-catalyzed addition/cycloaddition domino reactions of beta'-acetoxy allenoate 1 have been developed. The reaction of 1 with 2-acyl-3-methyl-acrylonitrile 2 readily occurs to give 2-oxabicyclo[3.3.1]nonane 3, furnishing the beta'-addition/[4 + 4] cycloaddition domino sequence. In this sequence, beta'C of allenoate 1 is an electrophilic center, and its beta'C and gamma C serve as a 1,4-dipole. When the other reaction partner is switched to 2-acyl-3-(2-pyrrole)-acrylonitrile 8, a gamma-addition/[3 + 2] cycloaddition domino reaction is instead observed, in which allenoate 1 exhibits dual electrophilic reactivity of gamma C and 1,3-dipole chemical behavior of beta C and beta'C. Furthermore, both of these two asymmetric variants have also been achieved with up to 93% ee. The domino reactions presented in this report are valuable for highly stereoselective construction of complex structures under mild reaction conditions.

  DOI：

  10.1021/jacs.5b03273
• 作为产物：
  描述：

  2-吡咯甲醛 、 苯甲酰乙腈 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以85%的产率得到2-benzoyl-3-(2-pyrrole)acrylonitrile
  参考文献：
  名称：

  与 2-氨基苯并咪唑的反应：几种新型嘧啶并 [1,2-a] 苯并咪唑衍生物的合成

  摘要：

  通过2-氨基苯并咪唑与α,β-不饱和腈和苯甲酰乙腈衍生物反应合成了几种新的嘧啶并[1,2-a]苯并咪唑衍生物。产物的结构是在元素分析、IR 和 1H-NMR 光谱数据的基础上确定的。

  DOI：

  10.1002/ardp.19873200714

文献信息

• Magnesium Halide‐Catalyzed Synthesis of Oxaspiro[2.5]octenes from a Methylenecyclopropane and Acyl Cyanoalkenes
  作者：Itaru Suzuki、Kazuki Ogura、Jun‐ya Shimazu、Ikuya Shibata

  DOI：10.1002/ejoc.202100500

  日期：2021.5.20

  Novel transformation of methylenecyclopropanes (MCPs) with acyl cyanoalkenes has been achieved to give oxaspiro[2.5]octenes. This annulation is successfully catalyzed by magnesium halides under mild reaction conditions, and shows a broad functional group tolerance. The reaction includes a rare reaction course, which involves an intramolecular oxa-Michael addition of Mg enolate after the ring opening

  已经实现了用酰基氰基烯烃对亚甲基环丙烷（MCPs）的新型转化，从而生成了氧杂螺[2.5]辛烯。在温和的反应条件下，这种环化反应成功地由卤化镁催化，并显示出宽泛的官能团耐受性。该反应包括一个罕见的反应过程，该过程涉及在MCP开环后分子内将Mg烯醇氧加到Oxa-Michael并加到烯烃中。没有在我们的实验室中以前观察到的典型的分子内烯醇镁的迈克尔加成反应，导致形成螺[2.3]己烷。
• Asymmetric Sequential Corey–Chaykovsky Cyclopropanation/Cloke–Wilson Rearrangement for the Synthesis of 2,3-Dihydrofurans
  作者：Yiming Zhou、Ning Li、Wei Cai、You Huang

  DOI：10.1021/acs.orglett.1c03225

  日期：2021.11.19

  The first sequential Corey–Chaykovsky cyclopropanation/Cloke–Wilson rearrangement between propargyl sulfonium salts and acrylonitrile derivatives has been developed, affording the tetra-substituted 2,3-dihydrofurans in generally excellent yields (57–98%) with good diastereoselectivities (7:1–18:1). In addition, chiral propargyl sulfonium salt is also suitable for this strategy, giving the optically

  已经开发出了炔丙基锍盐和丙烯腈衍生物之间的第一个连续 Corey-Chaykovsky 环丙烷化/Cloke-Wilson 重排，提供了具有良好非对映选择性 (7:1) 的四取代 2,3-二氢呋喃–18:1）。此外，手性炔丙基锍盐也适用于该策略，使光学活性 2,3-二氢呋喃具有良好的对映选择性。该反应序列是根据吲哚片段的脱芳构化和随后的分子内 1,6-加成原位生成 10π-共轭结构而设计的。
• Construction of polycyclic frameworks via a DMAP-catalysed tandem addition–(4 + 2) annulation sequence of δ-acetoxy allenoate
  作者：Chunjie Ni、Yuejie Yuan、Yuwen Zhang、Jiangfei Chen、Dong Wang、Xiaofeng Tong

  DOI：10.1039/c7ob00688h

  日期：——

  Here is reported the DMAP-catalyzed addition/(4+2) annulation domino reaction of [small delta]-acetoxy allenoate with either salicylaldehyde-derived oxadiene or pyrrolealdehyde-derived oxadiene, which provides a facile method toward polycyclic frameworks. A cationic intermediate,...

  此处报道了小δ-乙酰氧基烯丙基酯与水杨醛衍生的恶二烯或吡咯醛衍生的恶二烯的DMAP催化的加成/（4 + 2）环化多米诺反应，其为多环骨架提供了一种简便的方法。阳离子中间体，...
• Annulation of a Methylenecyclopropane with Cyanoalkenes Catalyzed by Lewis Bases
  作者：Itaru Suzuki、Nozomi Kasahara、Kazuki Ogura、Ikuya Shibata

  DOI：10.1002/chem.202302365

  日期：2024.2.12

  A rare intermolecular annulation of donor–acceptor cyclopropanes with alkenes has been developed by using a methylenecyclopropane (MCP) and acyl cyanoalkenes to give dihydrofurans or furans. The dihydrofurans were synthesized in the presence of a catalytic amount of the base and were readily converted to the furans by using a stoichiometric amount of the base. A 1H NMR study revealed that the ring-opened

  通过使用亚甲基环丙烷（MCP）和酰基氰基烯烃，开发了一种罕见的供体-受体环丙烷与烯烃的分子间环化反应，得到二氢呋喃或呋喃。二氢呋喃是在催化量的碱存在下合成的，并且通过使用化学计量量的碱很容易转化为呋喃。 1 H NMR 研究表明，开环的 MCP 与烯烃发生反应。