(2Z)-Diethyl 2-(trimethylsilyl)-2-heptenyl phosphate | 168104-81-2

• 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: (2Z)-Diethyl 2-(trimethylsilyl)-2-heptenyl phosphate
• 英文别名: diethyl [(Z)-2-trimethylsilylhept-2-enyl] phosphate
• CAS: 168104-81-2
• 化学式: C₁₄H₃₁O₄PSi
• 分子量: 322.457
• InChiKey: AMXGIPURTGHGIH-OWBHPGMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  庚醛 、 (2Z)-Diethyl 2-(trimethylsilyl)-2-heptenyl phosphate 在 chromium dichloride 、 lithium iodide 作用下， 以 various solvent(s) 为溶剂， 反应 168.0h， 生成 (6R*,5R*)-5-<(1-Trimethylsilyl)ethenyl>dodecan-6-ol 、 (6R*,5S*)-5-<(1-Trimethylsilyl)ethenyl>dodecan-6-ol
  参考文献：
  名称：

  Chromium(II)-Mediated Stereodivergent Additions of Allylic Phosphates and Halides to Aldehydes

  摘要：

  The addition of gamma-disubstituted allylchromium(III) reagents to aldehydes proceeds in a stereodivergent manner, in contrast to the case of gamma-monosubstituted allylchromium(III) species. The method allows the preparation of a variety of homoallylic alcohols bearing a quaternary center of defined relative configuration in the alpha-position. The preparation of both stereomeric homoallylic alcohols 13 is possible by using either of the two (E)- or (Z)-allylic precursors. The reaction has been extended to a gamma-monosubstituted beta-(trimethylsilyl)allylic system. The intermediate allylic chromium(III) reagents can be conveniently prepared from the corresponding phosphates (or chlorides) in DMPU or THF in the presence of catalytic amounts of LiI.

  DOI：

  10.1021/jo00114a026
• 作为产物：
  描述：

  氯磷酸二乙酯 、 (Z)-2-(Trimethylsilyl)-2-hepten-1-ol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (2Z)-Diethyl 2-(trimethylsilyl)-2-heptenyl phosphate
  参考文献：
  名称：

  Chromium(II)-Mediated Stereodivergent Additions of Allylic Phosphates and Halides to Aldehydes

  摘要：

  The addition of gamma-disubstituted allylchromium(III) reagents to aldehydes proceeds in a stereodivergent manner, in contrast to the case of gamma-monosubstituted allylchromium(III) species. The method allows the preparation of a variety of homoallylic alcohols bearing a quaternary center of defined relative configuration in the alpha-position. The preparation of both stereomeric homoallylic alcohols 13 is possible by using either of the two (E)- or (Z)-allylic precursors. The reaction has been extended to a gamma-monosubstituted beta-(trimethylsilyl)allylic system. The intermediate allylic chromium(III) reagents can be conveniently prepared from the corresponding phosphates (or chlorides) in DMPU or THF in the presence of catalytic amounts of LiI.

  DOI：

  10.1021/jo00114a026

文献信息

• Chromium(II)-Mediated Stereodivergent Additions of Allylic Phosphates and Halides to Aldehydes
  作者：Stefan Nowotny、Charles E. Tucker、Carole Jubert、Paul Knochel

  DOI：10.1021/jo00114a026

  日期：1995.5

  The addition of gamma-disubstituted allylchromium(III) reagents to aldehydes proceeds in a stereodivergent manner, in contrast to the case of gamma-monosubstituted allylchromium(III) species. The method allows the preparation of a variety of homoallylic alcohols bearing a quaternary center of defined relative configuration in the alpha-position. The preparation of both stereomeric homoallylic alcohols 13 is possible by using either of the two (E)- or (Z)-allylic precursors. The reaction has been extended to a gamma-monosubstituted beta-(trimethylsilyl)allylic system. The intermediate allylic chromium(III) reagents can be conveniently prepared from the corresponding phosphates (or chlorides) in DMPU or THF in the presence of catalytic amounts of LiI.