Diethyl 3-methylhept-2(Z)-enyl phosphate | 144375-46-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Diethyl 3-methylhept-2(Z)-enyl phosphate
• 英文别名: diethyl [(Z)-3-methylhept-2-enyl] phosphate
• CAS: 144375-46-2
• 化学式: C₁₂H₂₅O₄P
• 分子量: 264.302
• InChiKey: JUMCSFLIRKIJIB-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  苯甲醛 、 Diethyl 3-methylhept-2(Z)-enyl phosphate 在 chromium dichloride 、 lithium iodide 作用下， 以 various solvent(s) 为溶剂， 以95%的产率得到(1S*,2R*)-2-Ethenyl-2-methyl-1-phenyl-1-hexanol
  参考文献：
  名称：

  Stereodivergent additions of allylic chromium(III) reagents to aldehydes

  摘要：

  In contrast to gamma-monosubstituted allylic chromium reagents, gamma-disubstituted allylic chromium(III) organometallics undergo highly stereoselective stereodivergent additions to aldehydes.

  DOI：

  10.1021/jo00050a005
• 作为产物：
  描述：

  (Z)-3-methylhept-2-en-1-ol 、 氯磷酸二乙酯 在 吡啶 作用下， 生成 Diethyl 3-methylhept-2(Z)-enyl 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.
• Stereodivergent additions of allylic chromium(III) reagents to aldehydes
  作者：Carole Jubert、Stefan Nowotny、Dirk Kornemann、Iris Antes、Charles E. Tucker、Paul Knochel

  DOI：10.1021/jo00050a005

  日期：1992.11

  In contrast to gamma-monosubstituted allylic chromium reagents, gamma-disubstituted allylic chromium(III) organometallics undergo highly stereoselective stereodivergent additions to aldehydes.