(S)-4-((E)-Hex-2-enyl)-2-oxo-4,7-dihydro-2λ⁵-[1,3,2]dioxaphosphepin-2-ol | 862973-41-9

• 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: (S)-4-((E)-Hex-2-enyl)-2-oxo-4,7-dihydro-2λ⁵-[1,3,2]dioxaphosphepin-2-ol
• 英文别名: (4S)-4-[(E)-hex-2-enyl]-2-hydroxy-4,7-dihydro-1,3,2lambda5-dioxaphosphepine 2-oxide；(4S)-4-[(E)-hex-2-enyl]-2-hydroxy-4,7-dihydro-1,3,2λ5-dioxaphosphepine 2-oxide
• CAS: 862973-41-9
• 化学式: C₁₀H₁₇O₄P
• 分子量: 232.216
• InChiKey: VKKWMAZLQDQKFS-YEZKRMTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-((E)-Hex-2-enyl)-2-oxo-4,7-dihydro-2λ⁵-[1,3,2]dioxaphosphepin-2-ol 在 红铝 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以21 mg的产率得到(S,2Z,6E)-deca-2,6-diene-1,4-diol
  参考文献：
  名称：

  Multivalent Activation in Temporary Phosphate Tethers:  A New Tether for Small Molecule Synthesis

  摘要：

  A new tether for small molecule synthesis is reported. This functionally active tether mediates the desymmetrization of a pseudo-C-2-symmetric tris-allylic phosphate triester to generate a P-chiral bicyclo[4.3.1]phosphate containing ample steric and stereoelectronic differentiation for investigating chemo-, regio-, and stereoselective transformations. Overall, the method reported herein demonstrates a fundamentally new role of phosphates in synthesis and provides differentiated polyol building blocks for use in natural product synthesis.

  DOI：

  10.1021/ol0512886
• 作为产物：
  描述：

  (3S,5S)-hepta-1,6-diene-3,5-diol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 、 lithium chloride 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.67h， 生成 (S)-4-((E)-Hex-2-enyl)-2-oxo-4,7-dihydro-2λ⁵-[1,3,2]dioxaphosphepin-2-ol
  参考文献：
  名称：

  Multivalent Activation in Temporary Phosphate Tethers:  A New Tether for Small Molecule Synthesis

  摘要：

  A new tether for small molecule synthesis is reported. This functionally active tether mediates the desymmetrization of a pseudo-C-2-symmetric tris-allylic phosphate triester to generate a P-chiral bicyclo[4.3.1]phosphate containing ample steric and stereoelectronic differentiation for investigating chemo-, regio-, and stereoselective transformations. Overall, the method reported herein demonstrates a fundamentally new role of phosphates in synthesis and provides differentiated polyol building blocks for use in natural product synthesis.

  DOI：

  10.1021/ol0512886

文献信息

• Multivalent Activation in Temporary Phosphate Tethers:  A New Tether for Small Molecule Synthesis
  作者：Alan Whitehead、Matthew D. McReynolds、Joel D. Moore、Paul R. Hanson

  DOI：10.1021/ol0512886

  日期：2005.7.1

  A new tether for small molecule synthesis is reported. This functionally active tether mediates the desymmetrization of a pseudo-C-2-symmetric tris-allylic phosphate triester to generate a P-chiral bicyclo[4.3.1]phosphate containing ample steric and stereoelectronic differentiation for investigating chemo-, regio-, and stereoselective transformations. Overall, the method reported herein demonstrates a fundamentally new role of phosphates in synthesis and provides differentiated polyol building blocks for use in natural product synthesis.