2,2,2-trichloroethyl cinnamate | 74502-16-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2,2,2-trichloroethyl cinnamate
• 英文别名: Zimtsaeure-2.2.2-trichlorethylester；2,2,2-Trichloroethyl 3-phenylprop-2-enoate；2,2,2-trichloroethyl 3-phenylprop-2-enoate
• CAS: 74502-16-2
• 化学式: C₁₁H₉Cl₃O₂
• 分子量: 279.55
• InChiKey: DQTDGMYJUFKFIX-UHFFFAOYSA-N

物化性质

• 沸点：
  368.0±42.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl cinnamate 在 2,2'-联吡啶 、 copper(l) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以92%的产率得到1-chloroethenyl cinnamate
  参考文献：
  名称：

  Copper(I)-Promoted Dechlorinative Surzur−Tanner Rearrangement of 2,2,2-Trichloroethyl Carboxylates

  摘要：

  [GRAPHICS]2,2,2-Trichloroethyl carboxylates undergo highly efficient dechlorinative Surzur-Tanner rearrangement with 2 equiv of a 1:1 molar mixture of CuCl and bpy in boiling DCE to give 1-chloroethenyl carboxylates in which copper appears to play an important role, probably by coordinating the initial radical or as a Lewis acid catalyst.

  DOI：

  10.1021/ol027139u
• 作为产物：
  描述：

  別桂皮酸 在 氯化亚砜 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 2,2,2-trichloroethyl cinnamate
  参考文献：
  名称：

  Copper(I)-Promoted Dechlorinative Surzur−Tanner Rearrangement of 2,2,2-Trichloroethyl Carboxylates

  摘要：

  [GRAPHICS]2,2,2-Trichloroethyl carboxylates undergo highly efficient dechlorinative Surzur-Tanner rearrangement with 2 equiv of a 1:1 molar mixture of CuCl and bpy in boiling DCE to give 1-chloroethenyl carboxylates in which copper appears to play an important role, probably by coordinating the initial radical or as a Lewis acid catalyst.

  DOI：

  10.1021/ol027139u

文献信息

• Water is an efficient medium for Wittig reactions employing stabilized ylides and aldehydes
  作者：Jesse Dambacher、Wen Zhao、Amer El-Batta、Robert Anness、Changchun Jiang、Mikael Bergdahl

  DOI：10.1016/j.tetlet.2005.04.105

  日期：2005.6

  Water is demonstrated to be an excellent medium for the Wittig reaction employing stabilized ylides and aldehydes. Although the solubility in water appears to be an unimportant characteristic in achieving good chemical yields and E/Z-ratios, the rate of Wittig reactions in water is unexpectedly accelerated.

  事实证明，水是采用稳定化的丙烯化物和醛类进行维蒂希反应的极佳介质。尽管在水中的溶解度对于获得良好的化学收率和E / Z-比值似乎不是重要的特征，但是水中的维蒂希反应速率却出乎意料地加快了。
• N-Heterocyclic carbene-catalyzed oxidations
  作者：Brooks E. Maki、Audrey Chan、Eric M. Phillips、Karl A. Scheidt

  DOI：10.1016/j.tet.2008.10.033

  日期：2009.4

  N-Hererocyclic carbenes catalyze the oxidation of allylic and benzylic alcohols as well as saturated aldehydes to esters with manganese(IV) oxide in excellent yields. A variety of esters can be synthesized,, protected carboxylates. The oxidation proceeds Under mild conditions, with low loadings of including a simple triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable triazolium salt pre-catalyst in the presence of base. Substrates containing potentially epimerizable centers are oxidized while preserving stereochemical integrity. The acyl triazolium intermediate generated under catalytic conditions can be employed as a chiral acylating agent in the desymmetrization of meso-diols.
• Copper(I)-Promoted Dechlorinative Surzur−Tanner Rearrangement of 2,2,2-Trichloroethyl Carboxylates
  作者：Ram、Nabin Kumar Meher

  DOI：10.1021/ol027139u

  日期：2003.1.1

  [GRAPHICS]2,2,2-Trichloroethyl carboxylates undergo highly efficient dechlorinative Surzur-Tanner rearrangement with 2 equiv of a 1:1 molar mixture of CuCl and bpy in boiling DCE to give 1-chloroethenyl carboxylates in which copper appears to play an important role, probably by coordinating the initial radical or as a Lewis acid catalyst.