O-ethyl [(1S,3R)-2,2-dimethyl-3-[2-(2-methyl-1,3-dithiolan-2-yl)ethyl]cyclopropanecarbonyl]sulfanylmethanethioate | 823797-68-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: O-ethyl [(1S,3R)-2,2-dimethyl-3-[2-(2-methyl-1,3-dithiolan-2-yl)ethyl]cyclopropanecarbonyl]sulfanylmethanethioate
• CAS: 823797-68-8
• 化学式: C₁₅H₂₄O₂S₄
• 分子量: 364.618
• InChiKey: GCOCHDXOHUUAIA-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O-ethyl [(1S,3R)-2,2-dimethyl-3-[2-(2-methyl-1,3-dithiolan-2-yl)ethyl]cyclopropanecarbonyl]sulfanylmethanethioate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (E)-1-{(1S,3R)-2,2-dimethyl-3-[2-(2-methyl-[1,3]dithiolan-2-yl)-ethyl]cyclopropyl}-3-trimethylsilanyl-propenone
  参考文献：
  名称：

  Generation and Intermolecular Capture of Cyclopropylacyl Radicals

  摘要：

  Cyclopropylacyl radicals derived from S-cyclopropylacyl xanthates (dithiocarbonates) undergo intermolecular additions to olefins without loss of CO or ring opening. In the presence of a phenyl ring on carbon C-1 of the cyclopropane ring, loss can be made to occur in the absence of an olefinic trap. The adducts from the cyclopropylacyl radical additions are easily converted into enones by base-induced beta-elimination of the xanthate group.

  DOI：

  10.1021/ol047892i
• 作为产物：
  描述：

  (1S,3R)-cis-2,2-dimethyl-3-(3-oxobutyl)cyclopropanecarboxylic acid 在 草酰氯 、 三氟化硼乙醚 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.75h， 生成 O-ethyl [(1S,3R)-2,2-dimethyl-3-[2-(2-methyl-1,3-dithiolan-2-yl)ethyl]cyclopropanecarbonyl]sulfanylmethanethioate
  参考文献：
  名称：

  Generation and Intermolecular Capture of Cyclopropylacyl Radicals

  摘要：

  Cyclopropylacyl radicals derived from S-cyclopropylacyl xanthates (dithiocarbonates) undergo intermolecular additions to olefins without loss of CO or ring opening. In the presence of a phenyl ring on carbon C-1 of the cyclopropane ring, loss can be made to occur in the absence of an olefinic trap. The adducts from the cyclopropylacyl radical additions are easily converted into enones by base-induced beta-elimination of the xanthate group.

  DOI：

  10.1021/ol047892i

文献信息

• Generation and Intermolecular Capture of Cyclopropylacyl Radicals
  作者：Markus R. Heinrich、Samir Z. Zard

  DOI：10.1021/ol047892i

  日期：2004.12.1

  Cyclopropylacyl radicals derived from S-cyclopropylacyl xanthates (dithiocarbonates) undergo intermolecular additions to olefins without loss of CO or ring opening. In the presence of a phenyl ring on carbon C-1 of the cyclopropane ring, loss can be made to occur in the absence of an olefinic trap. The adducts from the cyclopropylacyl radical additions are easily converted into enones by base-induced beta-elimination of the xanthate group.