3,3-dimethyl-5,5-diphenylpentyl (2,2,2-trifluoroethyl)sulfamate

• 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: 3,3-dimethyl-5,5-diphenylpentyl (2,2,2-trifluoroethyl)sulfamate
• 英文别名: (3,3-dimethyl-5,5-diphenylpentyl) N-(2,2,2-trifluoroethyl)sulfamate
• 化学式: C₂₁H₂₆F₃NO₃S
• 分子量: 429.504
• InChiKey: KBLQMCULJGYOAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,1-二苯乙烯 、 isopentyl (2,2,2-trifluoroethyl)sulfamate 在 disodium hydrogenphosphate 、 iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C₂₀]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate 作用下， 以 水 为溶剂， 反应 32.0h， 以89%的产率得到3,3-dimethyl-5,5-diphenylpentyl (2,2,2-trifluoroethyl)sulfamate
  参考文献：
  名称：

  γ-Alkylation of Alcohols Enabled by Visible-Light Induced 1,6-Hydrogen Atom Transfer

  摘要：

  Site-selective remote alkylation of alcohol is attractive but challenging in organic synthesis. Herein, we report a novel visible-light mediated gamma-alkylation of alcohol derivatives via the formation of C-sp3-C-sp3 bond through C-sp3-H bond functionalization under mild conditions. The use of sulfamate esters enables the directed, otherwise rare 1,6-HAT to generate gamma-selective C-centered radical, which is complementary to delta-selective 1,5-HAT of alcohols. This redox-neutral protocol provides a general and operationally simple method to access gamma-alkylated alcohols.

  DOI：

  10.1021/acs.orglett.9b02255

文献信息

• <i>γ</i>-Alkylation of Alcohols Enabled by Visible-Light Induced 1,6-Hydrogen Atom Transfer
  作者：Wei Shu、Hui Zhang、Yan Huang

  DOI：10.1021/acs.orglett.9b02255

  日期：2019.8.2

  Site-selective remote alkylation of alcohol is attractive but challenging in organic synthesis. Herein, we report a novel visible-light mediated gamma-alkylation of alcohol derivatives via the formation of C-sp3-C-sp3 bond through C-sp3-H bond functionalization under mild conditions. The use of sulfamate esters enables the directed, otherwise rare 1,6-HAT to generate gamma-selective C-centered radical, which is complementary to delta-selective 1,5-HAT of alcohols. This redox-neutral protocol provides a general and operationally simple method to access gamma-alkylated alcohols.