(1S,6R,8R)-3,3-Dimethyl-8-vinyl-2,9,10-trioxa-1-phospha-bicyclo[4.3.1]dec-4-ene 1-oxide | 887144-88-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (1S,6R,8R)-3,3-Dimethyl-8-vinyl-2,9,10-trioxa-1-phospha-bicyclo[4.3.1]dec-4-ene 1-oxide
• 英文别名: (1R,6R,8R)-8-ethenyl-3,3-dimethyl-2,9,10-trioxa-1lambda5-phosphabicyclo[4.3.1]dec-4-ene 1-oxide；(1R,6R,8R)-8-ethenyl-3,3-dimethyl-2,9,10-trioxa-1λ5-phosphabicyclo[4.3.1]dec-4-ene 1-oxide
• CAS: 887144-88-9
• 化学式: C₁₀H₁₅O₄P
• 分子量: 230.2
• InChiKey: QNAQEPYPXVOAJC-KOSWAMCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,6R,8R)-3,3-Dimethyl-8-vinyl-2,9,10-trioxa-1-phospha-bicyclo[4.3.1]dec-4-ene 1-oxide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 Hoveyda-Grubbs catalyst second generation 氢气 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 20.0~37.0 ℃ 、2.07 MPa 条件下， 反应 24.0h， 生成 (1S,6R,8S)-8-[4-(4-Methoxy-benzyloxy)-butyl]-3,3-dimethyl-2,9,10-trioxa-1-phospha-bicyclo[4.3.1]dec-4-ene 1-oxide
  参考文献：
  名称：

  Temporary Phosphate Tethers:  A Metathesis Strategy to Differentiated Polyol Subunits

  摘要：

  Studies probing reactivity and selectivity of cross metathesis (CM) with an exocyclic olefin in a P-chiral bicyclo[4.3.1]phosphate triester are described. Studies have revealed a Type III CM reactivity pattern for the exocyclic olefin within this phosphate triester. This versatile method allows for simple, selective manipulation of a P-chiral building block en route to advanced polyol subunits.

  DOI：

  10.1021/ol0602809
• 作为产物：
  描述：

  (4R,6R)-2-chloro-4,6-bis(ethenyl)-1,3,2lambda5-dioxaphosphinane 2-oxide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (1S,6R,8R)-3,3-Dimethyl-8-vinyl-2,9,10-trioxa-1-phospha-bicyclo[4.3.1]dec-4-ene 1-oxide
  参考文献：
  名称：

  Temporary Phosphate Tethers:  A Metathesis Strategy to Differentiated Polyol Subunits

  摘要：

  Studies probing reactivity and selectivity of cross metathesis (CM) with an exocyclic olefin in a P-chiral bicyclo[4.3.1]phosphate triester are described. Studies have revealed a Type III CM reactivity pattern for the exocyclic olefin within this phosphate triester. This versatile method allows for simple, selective manipulation of a P-chiral building block en route to advanced polyol subunits.

  DOI：

  10.1021/ol0602809

文献信息

• Temporary Phosphate Tethers:  A Metathesis Strategy to Differentiated Polyol Subunits
  作者：Joshua D. Waetzig、Paul R. Hanson

  DOI：10.1021/ol0602809

  日期：2006.4.1

  Studies probing reactivity and selectivity of cross metathesis (CM) with an exocyclic olefin in a P-chiral bicyclo[4.3.1]phosphate triester are described. Studies have revealed a Type III CM reactivity pattern for the exocyclic olefin within this phosphate triester. This versatile method allows for simple, selective manipulation of a P-chiral building block en route to advanced polyol subunits.