Dimethyl 2-(3,3-dimethyl-5-thiophen-2-ylhexylidene)propanedioate | 866466-95-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Dimethyl 2-(3,3-dimethyl-5-thiophen-2-ylhexylidene)propanedioate
• 英文别名: dimethyl 2-(3,3-dimethyl-5-thiophen-2-ylhexylidene)propanedioate
• CAS: 866466-95-7
• 化学式: C₁₇H₂₄O₄S
• 分子量: 324.441
• InChiKey: FCPGUVJLRZNJHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Dimethyl 2-(3,3-dimethyl-5-thiophen-2-ylhexylidene)propanedioate 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以68%的产率得到Dimethyl 2,4,4-trimethyl-2-thiophen-2-ylcyclohexane-1,1-dicarboxylate
  参考文献：
  名称：

  Room Temperature Hydroalkylation of Electron-Deficient Olefins:  sp³ C−H Functionalization via a Lewis Acid-Catalyzed Intramolecular Redox Event

  摘要：

  A practical method for the intramolecular hydroalkylation of electron-deficient olefins has been developed. The direct transformation of benzylic, tertiary, and sterically hindered secondary sp3 C-H bonds into C-C bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.

  DOI：

  10.1021/ja053337f
• 作为产物：
  描述：

  6-庚烯-2-酮,4,4-二甲基- 在 三乙基硅烷 、 sodium periodate 、 四氧化锇 、 正丁基锂 、 三氟化硼乙醚 、 L-脯氨酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 35.42h， 生成 Dimethyl 2-(3,3-dimethyl-5-thiophen-2-ylhexylidene)propanedioate
  参考文献：
  名称：

  Room Temperature Hydroalkylation of Electron-Deficient Olefins:  sp³ C−H Functionalization via a Lewis Acid-Catalyzed Intramolecular Redox Event

  摘要：

  A practical method for the intramolecular hydroalkylation of electron-deficient olefins has been developed. The direct transformation of benzylic, tertiary, and sterically hindered secondary sp3 C-H bonds into C-C bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.

  DOI：

  10.1021/ja053337f

文献信息

• Room Temperature Hydroalkylation of Electron-Deficient Olefins:  sp³ C−H Functionalization via a Lewis Acid-Catalyzed Intramolecular Redox Event
  作者：Stefan J. Pastine、Kevin M. McQuaid、Dalibor Sames

  DOI：10.1021/ja053337f

  日期：2005.9.1

  A practical method for the intramolecular hydroalkylation of electron-deficient olefins has been developed. The direct transformation of benzylic, tertiary, and sterically hindered secondary sp3 C-H bonds into C-C bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.