methyl (2E)-2-[4-(methylsulfanyl)benzylidene]butanoate | 1246268-47-2

• 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: methyl (2E)-2-[4-(methylsulfanyl)benzylidene]butanoate
• 英文别名: methyl (2E)-2-[(4-methylsulfanylphenyl)methylidene]butanoate
• CAS: 1246268-47-2
• 化学式: C₁₃H₁₆O₂S
• 分子量: 236.335
• InChiKey: CTCRYGZJXOXKCT-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2E)-2-[4-(methylsulfanyl)benzylidene]butanoate 在 二异丁基氢化铝 、 水 、 sodium acetate 作用下， 以 正己烷 、 二氯甲烷 、 甲醇 为溶剂， 反应 2.0h， 以89%的产率得到(2E)-2-[4-(methylsulfanyl)benzylidene]butan-1-ol
  参考文献：
  名称：

  An approach for the enantioselective synthesis of biologically active furanones from a Morita–Baylis–Hillman adduct

  摘要：

  Herein, we disclose an approach for the asymmetric synthesis of both enantiomers of an anti-inflammatory furanone. The approach is based on the utilization of a Morita-Baylis-Hillman adduct as starting material and has as key step a selective epoxide-opening/benzylic oxidation mediated by Palladium (II). This sequence afforded an advanced intermediate, which was used to accomplish the total synthesis. Experimental evidences allowed us to suggest a mechanistic proposal for the oxidation Palladium(II)-mediated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.077
• 作为产物：
  描述：

  (+/-)-methyl 2-((acetyloxy)[4-(methylsulfanyl)phenyl]methyl)acrylate 、 甲基锂 在 copper(l) iodide 作用下， 以 乙醚 为溶剂， 反应 8.0h， 以60%的产率得到methyl (2E)-2-[4-(methylsulfanyl)benzylidene]butanoate
  参考文献：
  名称：

  An approach for the enantioselective synthesis of biologically active furanones from a Morita–Baylis–Hillman adduct

  摘要：

  Herein, we disclose an approach for the asymmetric synthesis of both enantiomers of an anti-inflammatory furanone. The approach is based on the utilization of a Morita-Baylis-Hillman adduct as starting material and has as key step a selective epoxide-opening/benzylic oxidation mediated by Palladium (II). This sequence afforded an advanced intermediate, which was used to accomplish the total synthesis. Experimental evidences allowed us to suggest a mechanistic proposal for the oxidation Palladium(II)-mediated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.077