O-Ethyl 3-phenylthio-2-propenoate | 73818-80-1

• 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: O-Ethyl 3-phenylthio-2-propenoate
• 英文别名: thiocinnamate d'ethyle；O-ethyl 3-phenyl-2-propenethioic acid；O-ethyl 3-phenylpropenethioate；ethyl thionocinnamate；O-ethyl 3-phenylprop-2-enethioate
• CAS: 73818-80-1
• 化学式: C₁₁H₁₂OS
• 分子量: 192.282
• InChiKey: BBGYVZJRHVBAEI-UHFFFAOYSA-N

物化性质

• 沸点：
  80 °C(Press: 0.2 Torr)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  41.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-Ethyl 3-phenylthio-2-propenoate 在 镍 作用下， 以 乙醚 为溶剂， 生成 (3-乙氧基丙基)苯
  参考文献：
  名称：

  Formation of ethers by the reductive desulfurization of thiono esters

  摘要：

  DOI：

  10.1021/jo00155a048
• 作为产物：
  描述：

  肉桂酸乙酯 在 tetraphosphorus decasulfide 、 六甲基二硅氧烷 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以72%的产率得到O-Ethyl 3-phenylthio-2-propenoate
  参考文献：
  名称：

  用五硫化二磷和六甲基二硅氧烷的试剂组合进行亚硫酰化。

  摘要：

  P4S10和六甲基二硅氧烷的组合可将酯，内酯，酰胺，内酰胺和酮有效地转化为其相应的硫代衍生物。在元素硫的存在下，该试剂将3-氧代酯转化为二硫代硫酮。产率与使用劳森试剂获得的产率相当或更高。该方法的优点在于，可以通过简单的水解后处理或通过硅胶过滤而不是通过劳氏试剂所要求的色谱法来除去试剂衍生的副产物。

  DOI：

  10.1021/jo0256742

文献信息

• Thionation of esters and lactones with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane
  作者：Thomas J Curphey

  DOI：10.1016/s0040-4039(01)02144-x

  日期：2002.1

  The combination of P4S10 and hexamethyldisiloxane converts esters and lactones to thionoesters and thionolactones in yields comparable to or superior to those obtained with Lawesson's reagent. The method has the advantage that reagent-derived byproducts may be removed by a simple hydrolytic workup or by filtration through silica gel, rather than by chromatography, as required for Lawesson's reagent. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Novel natural product-based cinnamates and their thio and thiono analogs as potent inhibitors of cell adhesion molecules on human endothelial cells
  作者：Sarvesh Kumar、Brajendra K. Singh、Pragya Arya、Shashwat Malhotra、Rajesh Thimmulappa、Ashok K. Prasad、Erik Van der Eycken、Carl E. Olsen、Anthony L. DePass、Shyam Biswal、Virinder S. Parmar、Balaram Ghosh

  DOI：10.1016/j.ejmech.2011.09.008

  日期：2011.11

  In the present study, we report the design and synthesis of novel analogs of cinnamates, thiocinnamates and thionocinnamates and evaluated the potencies of these analogs to inhibit TNF-alpha induced ICAM-1 expression on human endothelial cells. By using whole cell-ELISA, our screening data demonstrated that ethyl 3',4',5'-trimethoxythionocinnamate (ETMTC) is the most potent inhibitor of TNF-alpha induced ICAM-1, VCAM-1 and E-selectin. As functional consequences, ETMTC abrogated TNF-alpha induced adhesion of neutrophils to the endothelial monolayer. Structure activity relationship studies revealed the critical role of the chain-length of the alkyl group in the alcohol moiety, number of methoxy groups in the aromatic ring of the cinnamoyl moiety and the presence of the alpha, beta- C-C double bond in the thiocinnamates and thionocinnamates. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Difluorination of esters. Preparation of .alpha.,.alpha.-difluoro ethers
  作者：William H. Bunnelle、Bradley R. McKinnis、B. A. Narayanan

  DOI：10.1021/jo00289a067

  日期：1990.1
• Fischer, Helmut; Treier, Kornelia; Troll, Carsten, Chemische Berichte, 1995, vol. 128, # 9, p. 883 - 890
  作者：Fischer, Helmut、Treier, Kornelia、Troll, Carsten

  DOI：——

  日期：——
• Guerrera; Sarva; Siracusa, Farmaco, Edizione Scientifica, 1988, vol. 43, # 6, p. 551 - 558
  作者：Guerrera、Sarva、Siracusa、Ronsisvalle、Conforto、Dibennardo、Failla、Matera

  DOI：——

  日期：——