3'-phenyl-2'(E)-propenyl 2-propynoate | 29584-68-7

• 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: 3'-phenyl-2'(E)-propenyl 2-propynoate
• 英文别名: (3-phenyl-2-propene-1-yl) propiolate；Propiolansaeure-trans-zimtalkoholester；[(E)-3-phenylprop-2-enyl] prop-2-ynoate
• CAS: 29584-68-7
• 化学式: C₁₂H₁₀O₂
• 分子量: 186.21
• InChiKey: CYJWUSOJOVLXMI-RMKNXTFCSA-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：

  3'-phenyl-2'(E)-propenyl 2-propynoate 在 水 、 potassium thioacyanate 作用下， 反应 10.0h， 以78%的产率得到cinnamyl (Z)-3-thiocyanatoacrylate
  参考文献：
  名称：

  Deep eutectic solvent promoted hydrothiocyanation of alkynoates leading to Z-3-thiocyanatoacrylates

  摘要：

  A mild and efficient protocol for the selective construction of Z-3-thiocyanatoacrylates is described. Various alkynoates reacted with KSCN and H2O by using cheap and recyclable deep eutectic solvent as the catalyst and reaction media to produce the corresponding products in excellent yields with mild reaction conditions and wide substrate scope. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2019.07.014
• 作为产物：
  描述：

  3-苯基丙-2-烯-1-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 乙醚 为溶剂， 以64%的产率得到3'-phenyl-2'(E)-propenyl 2-propynoate
  参考文献：
  名称：

  Dihydropyridine derivative

  摘要：

  二氢吡啶衍生物具有以下结构式，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，如脑梗死发作后急性期内由缺血引起的脑病、脑出血或类似疾病、阿尔茨海默病等。

  公开号：

  US06350766B1

文献信息

• Synthesis of functionalized carbo- and heterocycles via gold-catalyzed cycloisomerization reactions of enynes
  作者：Lucie Leseurre、Chung-Meng Chao、Tomohiro Seki、Emilie Genin、Patrick Y. Toullec、Jean-Pierre Genêt、Véronique Michelet

  DOI：10.1016/j.tet.2008.11.105

  日期：2009.2

  conditions were compatible with various functional groups on the nucleophiles. Severe limitations were observed when the allylic position of the enyne is substituted by electron-withdrawing groups. The mechanism of the reaction was investigated via the synthesis of a deuterated aromatic ring: we showed that the source of proton involved in the protodemetallation step originates from the acidic activated

  PPh 3 AuCl / AgSbF 6催化体系促进了Friedel-Crafts串联式将富电子的芳族和杂芳族衍生物加到未活化的烯烃中，然后进行C-C键环化反应。该系统的效率允许在很短的时间内进行室温反应。研究了该反应的范围和局限性。反应条件与亲核试剂上的各种官能团相容。当烯炔的烯丙基位置被吸电子基团取代时，观察到严重的局限性。通过氘代芳环的合成研究了反应机理：我们表明，参与原金属脱金属步骤的质子源于亲核试剂的酸性活化C-H键。
• Ultrasound-promoted Brønsted acid ionic liquid-catalyzed hydrothiocyanation of activated alkynes under minimal solvent conditions
  作者：Chao Wu、Ling-Hui Lu、Ai-Zhong Peng、Guo-Kai Jia、Cun Peng、Zhong Cao、Zilong Tang、Wei-Min He、Xinhua Xu

  DOI：10.1039/c8gc00491a

  日期：——

  protocol for the synthesis of Z-vinyl thiocyanates through ultrasound-promoted Brønsted acid ionic liquid-catalyzed hydrothiocyanation of activated alkynes under minimal solvent conditions has been developed. This process effectively avoids the use of organic solvents, metal catalysts and harsh reaction conditions. This reaction shows attractive characteristics such as operational simplicity, broad substrate

  通过使用水作为氢源，已开发了一种环保且实用的方案，可在最小的溶剂条件下通过超声促进的布朗斯台德酸离子液体催化的炔烃氢硫氰化来合成Z-乙烯基硫氰酸酯。该过程有效地避免了使用有机溶剂，金属催化剂和苛刻的反应条件。该反应显示出诱人的特性，例如操作简便，具有良好的优良收率的宽范围的底物，易于规模化生产和高能源效率以及可回收和可重复使用的催化剂。
• Intramolecular cyclization of allylic propiolates mediated by the addition of stannyl radicals: A new synthetic route to α-methylene-γ-butyrolactones
  作者：Eun Lee、Sung Bo Ko、Kyung Woon Jung、Moon Ho Chang

  DOI：10.1016/s0040-4039(01)80626-2

  日期：1989.1

  Allylic propiolates react with tributyl- or triphenylstannane to yield α-(stannyl)methylene-γ-butyrolactones. α-Methylene-γ-butyrolactones are easily prepared by destannylation.

  烯丙基丙酸酯与三丁基锡或三苯基锡烷反应生成α-（锡烷基）亚甲基-γ-丁内酯。α-亚甲基-γ-丁内酯很容易通过脱锡反应制备。
• Novel dihydropyridine derivative
  申请人：AJINOMOTO CO., INC.

  公开号：US20020111494A1

  公开（公告）日：2002-08-15

  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. 1

  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，例如在脑梗死、脑出血等急性期缺血引起的脑病、阿尔茨海默病等方面。
• NOVEL DIHYDROPYRIDINE DERIVATIVE
  申请人：Ajinomoto Co., Inc.

  公开号：EP0985667A1

  公开（公告）日：2000-03-15

  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.

  下式的二氢吡啶衍生物、其类似物及其药学上可接受的盐类具有选择性抑制 N 型钙通道作用的活性。它们可用于治疗与 N 型钙通道有关的各种疾病，如脑梗塞、脑出血等发病后急性期缺血引起的脑病、阿尔茨海默病等。