(E)-ethyl 3-(cyclohexylthio)acrylate | 1351708-19-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: (E)-ethyl 3-(cyclohexylthio)acrylate
• CAS: 1351708-19-4
• 化学式: C₁₁H₁₈O₂S
• 分子量: 214.329
• InChiKey: ILVSVODQKDROGX-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  环己硫醇 、 顺式-3-碘丙烯酸乙酯 在 copper(I) oxide 、 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以72%的产率得到(Z)-ethyl 3-(cyclohexylthio)acrylate
  参考文献：
  名称：

  Efficient Copper-Catalyzed S-Vinylation of Thiols with Vinyl Halides

  摘要：

  The synthesis of vinyl sulfides through the coupling reaction of thiols with vinyl iodides, bromides, and chlorides is described. The thiols can couple with aryl iodides in the presence of only 0.5 mol % Cu2O without the need for an ancillary ligand. In the presence of 5 mol % of Cu2O and 10 mol % 1,10-phenanthroline as the ligand, the more challenging alkyl vinyl bromides can also be coupled with thiols, giving the vinyl sulfides in good to excellent yields.

  DOI：

  10.1021/ol2020863

文献信息

• One-pot synthesis of (Z)-β-sulfonyl enoates from ethyl propiolate
  作者：C. Wade Downey、Smaranda Craciun、Ana M. Neferu、Christina A. Vivelo、Carly J. Mueller、Brian C. Southall、Stephanie Corsi、Eric W. Etchill、Ryan J. Sault

  DOI：10.1016/j.tetlet.2012.08.051

  日期：2012.10

  β-Sulfonyl enoates may be synthesized through a one-pot two-step sequence from ethyl propiolate with good to excellent selectivity for the Z isomer. Trialkylamines catalyze thioconjugate additions of aryl thiols, and alkoxides catalyze the addition of aliphatic thiols. Addition of meta-chloroperbenzoic acid (mCPBA) and LiClO4 to the reaction mixture provides rapid access to the sulfonyl enoates. Yields

  β-磺酰基烯醇酸酯可以通过一锅两步的顺序由丙酸乙酯合成，对Z异构体具有良好的选择性。三烷基胺催化芳基硫醇的硫共轭加成，而醇盐催化脂肪族硫醇的加成。向反应混合物中加入间氯过苯甲酸（m CPBA）和LiClO 4可以快速获得磺酰基烯醇酸酯。纯Z异构体的产率为51-90％。