propynoic acid cinnamyl ester

• 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: propynoic acid cinnamyl ester
• 英文别名: (3-Phenyl-2-propene-1-yl) propiolate；3-phenylprop-2-enyl prop-2-ynoate
• 化学式: C₁₂H₁₀O₂
• 分子量: 186.21
• InChiKey: CYJWUSOJOVLXMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  potassium selenocyanate 、 propynoic acid cinnamyl ester 在 乳酸 、 水 作用下， 以94%的产率得到cinnamyl (Z)-3-selenocyanatoacrylate
  参考文献：
  名称：

  Sustainable routes for quantitative green selenocyanation of activated alkynes

  摘要：

  Most organic reactions require the usage of volatile organic compounds in the synthesis, work-up and purification processes, thus resulting in major environmental pollution and high manufacturing cost. By using cheap biomass lactic acid as the reaction media and catalyst, a sustainable protocol for the synthesis of Z-3-selenocyanatoacrylates and analogues through green selenocyanation of activated alkynes has been achieved. A principal advantage of this protocol is that the usage of organic volatile compounds can be avoided entirely, as the conversion of substrate is almost quantitative or quantitative with a minimal amount of lactic acid employed as reaction media, and the pure products can be conveniently collected through water precipitation. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.04.033
• 作为产物：
  描述：

  肉桂醇 、 丙炔酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 propynoic acid cinnamyl ester
  参考文献：
  名称：

  由有机膦加成到 Ynoates 引发的自由基偶联

  摘要：

  将已建立的有机膦的两个电子亲核催化与光氧化还原有机催化相结合，发现了机械上不寻常的吉斯偶联反应。除了解决传统光氧化还原与缺电子炔烃偶联的局限性之外，这些研究还证明了将传统亲核膦有机催化和光氧化还原事件结合起来的反应设计的可行性。

  DOI：

  10.1002/anie.202303869

文献信息

• Improved preparation of aliphatic propynoic esters
  作者：L. Balas、B. Jousseaume、B. Langwost

  DOI：10.1016/s0040-4039(01)80735-8

  日期：1989.1

  An improved procedure of esterification of propynoic acid, based on the N, N′-dicyclohexylcarbodiimide 4-dimethylaminopyridine condensation, is presented, which gives good results with primary, secondary, allylic and homoallylic alcohols. Reactions conditions are mild. Some limitations are given.

  提出了一种基于N，N'-二环己基碳二亚胺4-二甲基氨基吡啶缩合的丙酸酯化反应的改进方法，该方法与伯，仲，烯丙基和均烯丙基醇均能获得良好的结果。反应条件温和。给出了一些限制。
• Palladium-Catalyzed Decarboxylative Coupling of Allylic Alkynoates with Arynes
  作者：Shao-Feng Pi、Bo-Xiao Tang、Jin-Heng Li、Yi-Lin Liu、Yun Liang

  DOI：10.1021/ol900643r

  日期：2009.6.4

  A novel and selective protocol for the synthesis of 1-allyl-2-ethynylbenzenes has been developed by palladium-catalyzed decarboxylative coupling of allylic alkynoates with arynes. This new route allows for both sp−sp2 and sp2−sp3 couplings of allylic alkynoates with arynes in one pot involving a decarboxylation process.

  通过钯催化烯丙基炔酸与芳烃的脱羧偶联，已经开发出一种新颖且选择性的方案，用于合成1-烯丙基-2-乙炔基苯。这一新途径允许在一个罐中将烯丙基炔酸酯与芳烃的sp-sp 2和sp 2 -sp 3偶联，涉及脱羧过程。
• Selective difunctionalization of electron-deficient alkynes: access to (<i>E</i>)-2-iodo-3-(methylthio)acrylate
  作者：Ling-Hui Lu、Guangchuan Ou、Xiongjie Zhao、Yufei Wang、Xuelian Chen、Wenjun Liao、Shundan Li、Chao Wu

  DOI：10.1039/d1ob01287h

  日期：——

  A convenient and efficient approach to (E)-2-iodo-3-(methylthio)acrylate has been developed through direct iodothiomethylation of alkynes with aqueous HI and DMSO under mild conditions. This novel protocol has demonstrated a unique difunctionalization of electron-deficient alkynes with a broad substrate scope and excellent functional-group tolerance. Preliminary mechanistic studies indicated that prior

  通过在温和条件下用 HI 和 DMSO 水溶液直接碘硫甲基化炔烃，开发了一种方便有效的 ( E )-2-iodo-3-(甲硫基)丙烯酸酯方法。这种新颖的协议证明了缺电子炔烃的独特双功能化，具有广泛的底物范围和出色的官能团耐受性。初步机理研究表明，先对炔烃进行二碘化，然后用原位产生的 DMS 进行亲核取代，导致形成 ( E )-2-iodo-3-(methylthio) 丙烯酸酯。
• Palladium-Catalyzed Oxidative Diarylating Carbocyclization of Enynes
  作者：Min Jiang、Tuo Jiang、Jan-E. Bäckvall

  DOI：10.1021/ol301551x

  日期：2012.7.6

  efficient palladium-catalyzed oxidative diarylating carbocyclization of enynes is described. The reaction tolerates a range of functionalized arylboronic acids to give diarylated products in good yields. Control experiments suggest that the reaction starts with an arylpalladation of the alkyne, followed by carbocyclization, transmetalation, and reductive elimination to afford the diarylated product.

  描述了温和且有效的钯催化的炔烃的氧化二芳基化碳环化。该反应容许一系列官能化的芳基硼酸，以高收率得到二芳基化产物。对照实验表明，该反应以炔烃的芳基palladation开始，然后进行碳环化，金属转移和还原消除，得到二芳基化产物。
• Dihydropyridine derivative
  申请人：Ajinomoto Co., Inc.

  公开号：US06995179B2

  公开（公告）日：2006-02-07

  Dihydropyridine derivatives of the following formula, analogs thereof and pharmaceutically acceptable salts thereof have an activity of selectively inhibiting the action of N-type calcium channel. They are used as remedies for various diseases relating to the N-type calcium channel such as encephalopathies caused by the ischemia in the acute phase after the onset of cerebral infarction, cerebral hemorrhage or the like, Alzheimer's disease, etc.

  以下公式的二氢吡啶衍生物、其类似物和药学上可接受的盐具有选择性抑制N型钙通道作用的活性。它们被用作治疗与N型钙通道相关的各种疾病，如脑梗死、脑出血等急性期缺血引起的脑病，阿尔茨海默病等。