dithiocarbonic acid ethyl ester (1-phenylcyclopropyl) ester | 823797-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dithiocarbonic acid ethyl ester (1-phenylcyclopropyl) ester
• 英文别名: O-ethyl S-(1-phenylcyclopropyl) carbonodithioate；O-ethyl (1-phenylcyclopropyl)sulfanylmethanethioate
• CAS: 823797-72-4
• 化学式: C₁₂H₁₄OS₂
• 分子量: 238.375
• InChiKey: XGCKPHAMBAXTFB-UHFFFAOYSA-N

物化性质

• 沸点：
  352.2±12.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  66.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸烯丙酯 、 dithiocarbonic acid ethyl ester (1-phenylcyclopropyl) ester 在 DLP 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以22%的产率得到acetic acid 2-ethoxythiocarbonylsulfanyl-3-(1-phenylcyclopropyl)propyl 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：

  1-苯基-1-环丙羧酸 以 丙酮 为溶剂， 反应 1.75h， 生成 dithiocarbonic acid ethyl ester (1-phenylcyclopropyl) 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

文献信息

• Direct Decarboxylative Functionalization of Carboxylic Acids via O–H Hydrogen Atom Transfer
  作者：Christina G. Na、Davide Ravelli、Erik J. Alexanian

  DOI：10.1021/jacs.9b10825

  日期：2020.1.8

  Decarboxylative functionalization via hydrogen atom transfer offers an attractive alternative to standard redox approaches to this important class of transformations. Herein, we report a direct decarboxylative functionalization of aliphatic carboxylic acids using N-xanthylamides. The unique reactivity of amidyl radicals in hydrogen atom transfer enables decarboxylative xanthylation under redox-neutral

  通过氢原子转移进行的脱羧功能化为此类重要转化的标准氧化还原方法提供了一种有吸引力的替代方法。在此，我们报告了使用 N-黄原酰胺对脂肪族羧酸进行直接脱羧功能化。酰胺基自由基在氢原子转移中的独特反应性使得在氧化还原中性条件下脱羧黄嘌呤化成为可能。该平台通过黄药组的后续阐述提供了对一系列衍生物的便利访问。
• 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.