2-(4-氯苯甲酰基)-3-苯基丙烯腈 | 20412-92-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 2-(4-氯苯甲酰基)-3-苯基丙烯腈
• 英文名称: β-Cyano-β-(4-chlor-benzyliden)-acetophenon
• 英文别名: 2-(4-chlorobenzoyl)-3-phenylacrylonitrile；2-benzoyl-3-(4-chlorophenyl)acrylonitrile；2-Benzoyl-3-(4-chlorophenyl)prop-2-enenitrile
• CAS: 20412-92-4
• 化学式: C₁₆H₁₀ClNO
• 分子量: 267.714
• InChiKey: HPTGSTQTHHRAGY-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C
• 沸点：
  430.9±45.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 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：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-氯苯甲酰基)-3-苯基丙烯腈 在 三乙胺 氧气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 9-amino-8-benzoyl-7-(4-chlorophenyl)-11-oxopyrido[2,1-b]quinazoline-6-carbonitrile
  参考文献：
  名称：

  Aziz, M. A. Abdel; Daboun, H. A.; Gawad, S. M. Abdel, Journal fur praktische Chemie (Leipzig 1954), 1990, vol. 332, # 5, p. 610 - 618

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酸乙酯 在 哌啶 、 sodium hydride 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 19.0h， 生成 2-(4-氯苯甲酰基)-3-苯基丙烯腈
  参考文献：
  名称：

  Tandem cross-Rauhut–Currier/cyclization reactions of activated alkenes to give densely functionalized 3,4-dihydropyrans

  摘要：

  A novel tandem cross-Rauhut-Currier/cyclization reaction between alpha,beta-unsaturated ketones was developed. Using DABCO (20 mol %) as the catalyst, a series of densely functionalized 3,4-dihydropyrans were obtained in excellent yields and stereoselectivities (up to 98% yield, >99:1 dr). A tentative catalytic cycle was proposed with key intermediates confirmed by ESIMS studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.036

文献信息

• Facile synthesis of polysubstituted furans and dihydrofurans via cyclization of bromonitromethane with oxodienes
  作者：Rongshun Chen、Xia Fan、Zhaozhong Xu、Zhengjie He

  DOI：10.1016/j.tetlet.2017.08.027

  日期：2017.9

  A series of polysubstituted furans and dihydrofurans have been prepared from readily available oxodienes and bromonitromethane in modest to excellent yields. This facile synthetic method is developed on the basis of proprietary properties of nitro group such as strong electron-withdrawing ability and cleavability. The conversion of nitro-substituted dihydrofurans to furans is presumably realized by

  已经从容易获得的氧二烯和溴硝基甲烷以中等至优异的产率制备了一系列多取代的呋喃和二氢呋喃。这种简便的合成方法是基于硝基的专有特性（如强大的吸电子能力和可裂解性）而开发的。硝基取代的二氢呋喃向呋喃的转化大概是通过在DABCO的帮助下消除HNO 2来实现的。
• Construction of CF₃-Functionalized Fully Substituted Benzonitriles through Rauhut–Currier Reaction Initiated [3 + 3] Benzannulation
  作者：Qing Mao、Qian Zhao、Mu-Ze Li、Rui Qin、Meng-Lan Luo、Jing Xue、Ben-Hong Chen、Hai-Jun Leng、Cheng Peng、Gu Zhan、Bo Han

  DOI：10.1021/acs.joc.1c01631

  日期：2021.11.5

  Though numerous cyanation reactions have been developed for the synthesis of benzonitriles, the construction of valuable fully substituted benzonitriles is still a challenging task. Herein, we reported a tertiary amine-catalyzed [3 + 3]-benzannulation for the green synthesis of CF3-functionalized fully substituted benzonitriles. This strategy features exclusive chemoselectivity, high atom-economy,

  尽管已经开发了许多用于合成苯甲腈的氰化反应，但构建有价值的完全取代的苯甲腈仍然是一项具有挑战性的任务。在此，我们报道了一种叔胺催化的 [3 + 3] -苄基化反应，用于绿色合成 CF 3官能化的完全取代的苄腈。该策略具有独特的化学选择性、高原子经济性和良好的阶梯经济性，以及环境友好的试剂和温和的条件。使用这种方法可以快速构建独特的三苯基取代的二氰基苯甲酸酯产品。成功的放大合成证明了该反应的实用性和可靠性。一项机理研究表明 [3 + 3]-benzannulation 是由分子间 Rauhut-Currier 反应引发的。
• N-Heterocyclic Carbene Catalyzed [4+2] Cycloaddition of Nitroalkenes with Oxodienes
  作者：Xiang-Yu Chen、Li-Hui Sun、Song Ye

  DOI：10.1002/chem.201204539

  日期：2013.4.2

  NHC catalysis: N‐heterocyclic carbenes were found to be efficient catalysts for the unprecedented [4+2] cycloaddition of nitroalkenes and oxodienes, giving the corresponding dihydropyrans in good yield with good diastereoselectivity (see scheme). Deuteration experiment reveals that the reaction is possibly initiated by the addition of N‐heterocylic carbene to nitroalkenes.

  NHC催化：N-杂环卡宾被发现是硝基烯烃和氧二烯前所未有的[4 + 2]环加成反应的有效催化剂，从而以高收率和良好的非对映选择性提供相应的二氢吡喃（参见方案）。氘化实验表明，该反应可能是通过在硝基烯烃中添加N-杂环卡宾而引发的。
• Substituent‐Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and <i>Oxa</i> ‐Bridged Fused Heterocycles
  作者：Tianlong Zeng、Jingyang Kong、Hongkai Wang、Lingyan Liu、Weixing Chang、Jing Li

  DOI：10.1002/adsc.202100523

  日期：2021.8.13

  Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the

  在此，我们报告了在 PtI 2存在下查耳酮和芳基炔醇的取代基控制的发散级联环加成反应。根据查耳酮上的取代基，在相同的反应条件下，可以以 86-97% 和 87-95% 的产率获得螺缩酮或氧杂桥连的稠合杂环。进行对照实验以阐明高化学选择性的起源。这些为合成各种结构复杂的含氧杂环提供了一种方法。
• Tandem Access to Acridones and their Fused Derivatives: [1+2+3] Annulation of Isocyanides with Unsaturated Carbonyls
  作者：Ling‐Juan Zhang、Wenhui Yang、Zhongyan Hu、Xian‐Ming Zhang、Xianxiu Xu

  DOI：10.1002/adsc.201901560

  日期：2020.6.15

  acridones and their cyclo[b ]‐fused derivatives are efficiently constructed by a double annulation of o ‐enoyl arylisocyanides with α , β ‐unsaturated carbonyls under simple metal‐free condition. This protocol is general, efficient and practical, featuring the successive formation of two rings by a one‐pot domino transformation. A tandem process involing an isocyanide‐based [1+4] cycloaddition, an aminofuran‐based

  在简单的无金属条件下，通过邻烯基芳基异氰酸酯与α，β-不饱和羰基的双环化，可以有效地构建各种各样的a烯及其环[ b ]稠合衍生物。该协议是通用，高效和实用的，其特点是通过一锅多米诺骨牌变换连续形成两个环。提出了将异氰酸酯基[1 + 4]环加成，氨基呋喃基分子内[4 + 2]环加成，开环和芳构化等串联过程。