S-chlorodifluoromethyl O-octadecyl carbonodithioate | 1609974-69-7

• 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: S-chlorodifluoromethyl O-octadecyl carbonodithioate
• 英文别名: O-octadecyl [chloro(difluoro)methyl]sulfanylmethanethioate
• CAS: 1609974-69-7
• 化学式: C₂₀H₃₇ClF₂OS₂
• 分子量: 431.095
• InChiKey: ZSKOKBHJHWFNML-UHFFFAOYSA-N

物化性质

• 沸点：
  424.6±45.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  26
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  66.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione 、 S-chlorodifluoromethyl O-octadecyl carbonodithioate 在 过氧化双月桂酰 作用下， 反应 0.17h， 以80%的产率得到
  参考文献：
  名称：

  Radical Instability in Aid of Efficiency: A Powerful Route to Highly Functional MIDA Boronates

  摘要：

  The inability of the sp(3) boron in MIDA boronates to stabilize an adjacent radical makes possible the efficient addition of a wide array Of xanthates to vinyl MIDA boronate, leading to highly functionalized and diverse aliphatic organoboron structures. The lack of radical Stabilization also allows the exchange Of the Xanthate in the adducts with a bromine. In one case, the bromine was substituted to generate a cyclopropyl MIDA derivative.

  DOI：

  10.1021/jacs.5b03893
• 作为产物：
  描述：

  硬脂醇 在 sodium hydride 作用下， 以 四氢呋喃 、 环己烷 、 mineral oil 为溶剂， 反应 23.5h， 生成 S-chlorodifluoromethyl O-octadecyl carbonodithioate
  参考文献：
  名称：

  用于与 [18F] 氟化物进行亲核卤素交换的 2-（氯二氟甲基）吲哚的合成

  摘要：

  2-[ 18 F] 三氟甲基化吲哚是通过与 [ 18 F] 氟化物的无金属亲核卤素交换 (halex) 反应从 2-(氯二氟甲基) 吲哚获得的，而相对温和的条件是通过支持性消除-加成机制实现的在 2-甲基上。

  DOI：

  10.1002/ejoc.202100937

文献信息

• A Practical Source of Chlorodifluoromethyl Radicals. Convergent Routes to <i>gem</i>-Difluoroalkenes and -dienes and (2,2-Difluoroethyl)-indoles, -azaindoles, and -naphthols
  作者：Pierre Salomon、Samir Z. Zard

  DOI：10.1021/ol501063a

  日期：2014.6.6

  The preparation of O-octadecyl-S-chlorodifluoromethyl xanthate from chlorodifluoroacetic acid and its use as a convenient source of chlordifluoromethyl radicals is described. This reagent may be used to access gem-difluoroalkenes and -dienes, as well as (2,2-difluoroethyl)-indolines, -indoles, and -naphthols.
• Synthesis of 2‐(Chlorodifluoromethyl)indoles for Nucleophilic Halogen Exchange with [ ¹⁸ F]Fluoride
  作者：Leonard Bock、Stefanie K. Schultheiß、Simone Maschauer、Roman Lasch、Susanne Gradl、Olaf Prante、Samir Z. Zard、Markus R. Heinrich

  DOI：10.1002/ejoc.202100937

  日期：2021.12.14

  2-[18F]Trifluoromethylated indoles were obtained from 2-(chlorodifluoromethyl)indoles via a metal-free nucleophilic halogen exchange (halex) reaction with [18F]fluoride, whereat the comparably mild conditions are enabled by a supportive elimination-addition mechanism on the 2-methyl group.

  2-[ 18 F] 三氟甲基化吲哚是通过与 [ 18 F] 氟化物的无金属亲核卤素交换 (halex) 反应从 2-(氯二氟甲基) 吲哚获得的，而相对温和的条件是通过支持性消除-加成机制实现的在 2-甲基上。
• Radical Instability in Aid of Efficiency: A Powerful Route to Highly Functional MIDA Boronates
  作者：Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1021/jacs.5b03893

  日期：2015.6.3

  The inability of the sp(3) boron in MIDA boronates to stabilize an adjacent radical makes possible the efficient addition of a wide array Of xanthates to vinyl MIDA boronate, leading to highly functionalized and diverse aliphatic organoboron structures. The lack of radical Stabilization also allows the exchange Of the Xanthate in the adducts with a bromine. In one case, the bromine was substituted to generate a cyclopropyl MIDA derivative.