O-ethyl [1-(1,3-dioxoisoindol-2-yl)cyclopropanecarbonyl]sulfanylmethanethioate | 823797-58-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: O-ethyl [1-(1,3-dioxoisoindol-2-yl)cyclopropanecarbonyl]sulfanylmethanethioate
• CAS: 823797-58-6
• 化学式: C₁₅H₁₃NO₄S₂
• 分子量: 335.405
• InChiKey: JFMXUQOBXDQHMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O-ethyl [1-(1,3-dioxoisoindol-2-yl)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 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 (E)-2-tert-butoxycarbonylamino-6-[1-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-cyclopropyl]-6-oxo-hex-4-enoic acid methyl ester
  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：

  环丙羧酸,1-(1,3-二氢-1,3-二羰基-2H-异吲哚-2-基)- 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.25h， 生成 O-ethyl [1-(1,3-dioxoisoindol-2-yl)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

• A convergent approach to γ-carbonyl vinyl boronates
  作者：Markus R. Heinrich、Lisa A. Sharp、Samir Z. Zard

  DOI：10.1039/b502885j

  日期：——

  γ-Carbonyl vinyl boronates can be prepared by a visible light induced radical chain addition of an S-acyl dithiocarbonate (xanthate) to the pinacol ester of vinyl boronic acid, followed by treatment with base.

  γ-碳基乙烯硼酸酯可以通过可见光诱导的自由基链加成反应，将S-酰基二硫碳酸酯（黄药）与乙烯硼酸的匹卡醇酯反应，接着再用碱处理。
• 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.