2-chloro-1,3,2-oxathiaphospholane

• 分子结构分类: 有机化合物 - 有机磷化合物 - 有机硫代磷化合物
• 英文名称: 2-chloro-1,3,2-oxathiaphospholane
• 英文别名: 1,3,2-Oxathiaphospholane
• 化学式: C₂H₅OPS
• 分子量: 108.101
• InChiKey: CHXSLWJRKFESRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-羟基丙腈 、 2-chloro-1,3,2-oxathiaphospholane 在 吡啶 、 sulfur 作用下， 反应 60.0h， 以73%的产率得到2-cyanoethoxy-2-thiono-1,3,2-oxathiaphospholane
  参考文献：
  名称：

  An Oxathiaphospholane Approach to One-pot Phosphorothioylation of Isoprenoid Alcohols

  摘要：

  Allyl, isopentenyl, geranyl, citronellyl, farnesyl, and phytyl alcohols were transformed in good yield (>60%) into their phosphorothioates via a DBU-assisted 1,3,2-oxathiaphospholane ring-opening condensation with 2-(2-cyanoethoxy)-2-thiono-1,3,2-oxathiaphospholane, a reagent that is stable and easy to handle, followed by subsequent removal of the 2-cyanoethyl group from the intermediate phosphorothioate diester under basic conditions.

  DOI：

  10.1021/ol049771o

文献信息

• An Oxathiaphospholane Approach to One-pot Phosphorothioylation of Isoprenoid Alcohols
  作者：Katarzyna Zmudzka、Barbara Nawrot、Tadeusz Chojnacki、Wojciech J. Stec

  DOI：10.1021/ol049771o

  日期：2004.4.1

  Allyl, isopentenyl, geranyl, citronellyl, farnesyl, and phytyl alcohols were transformed in good yield (>60%) into their phosphorothioates via a DBU-assisted 1,3,2-oxathiaphospholane ring-opening condensation with 2-(2-cyanoethoxy)-2-thiono-1,3,2-oxathiaphospholane, a reagent that is stable and easy to handle, followed by subsequent removal of the 2-cyanoethyl group from the intermediate phosphorothioate diester under basic conditions.