(R*,R*)-2-(2-chloroethyl)-4,4,5-trimethyl-2-oxo-1,3,2-dioxaphospholane | 347868-18-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (R*,R*)-2-(2-chloroethyl)-4,4,5-trimethyl-2-oxo-1,3,2-dioxaphospholane
• 英文别名: 1,3,2-Dioxaphospholane, 2-(2-chloroethyl)-4,4,5-trimethyl-, 2-oxide, (2R,5R)-rel-；(2S,5S)-2-(2-chloroethyl)-4,4,5-trimethyl-1,3,2λ5-dioxaphospholane 2-oxide
• CAS: 347868-18-2
• 化学式: C₇H₁₄ClO₃P
• 分子量: 212.613
• InChiKey: YXYMVGPMTFEARS-QTTZVWFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-环氧-2-甲基丁烷 在 2,6-二甲基吡啶 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 苯 为溶剂， 反应 7.0h， 生成 (R*,R*)-2-(2-chloroethyl)-4,4,5-trimethyl-2-oxo-1,3,2-dioxaphospholane
  参考文献：
  名称：

  Study of the Addition of Monoalkylphosphonic Acids onto Trialkyl-Substituted Epoxides

  摘要：

  The addition of 2-chloroethylphosphonic acid (or ethephon), a well-known stimulating molecule for the production of latex by Hevea brasiliensis, onto 2,3-epoxy-2-methylbutane was investigated to enhance the understandings on the addition mechanisms of reagents of alkylphosphonic acid type onto trialkyl-substituted epoxides. It was demonstrated that the addition occurs according to a three-step mechanism including a rapid nucleophilic attack of the phosphorated anion on the most alkyl-substituted carbon of the oxirane, followed by formation of a dioxaphospholane structure with release of water, and finally a hydrolytic cleavage of the dioxaphospholane cycle to generate the regioisomer 1:1 adduct where the phosphorated group is on the less alkyl-substituted carbon of the initial oxirane.

  DOI：

  10.1021/jo001453p

文献信息

• Study of the Addition of Monoalkylphosphonic Acids onto Trialkyl-Substituted Epoxides
  作者：Daniel Derouet、Laurent Cauret、Jean-Claude Brosse

  DOI：10.1021/jo001453p

  日期：2001.6.1

  The addition of 2-chloroethylphosphonic acid (or ethephon), a well-known stimulating molecule for the production of latex by Hevea brasiliensis, onto 2,3-epoxy-2-methylbutane was investigated to enhance the understandings on the addition mechanisms of reagents of alkylphosphonic acid type onto trialkyl-substituted epoxides. It was demonstrated that the addition occurs according to a three-step mechanism including a rapid nucleophilic attack of the phosphorated anion on the most alkyl-substituted carbon of the oxirane, followed by formation of a dioxaphospholane structure with release of water, and finally a hydrolytic cleavage of the dioxaphospholane cycle to generate the regioisomer 1:1 adduct where the phosphorated group is on the less alkyl-substituted carbon of the initial oxirane.