(2S)-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadien-1-ol | 173289-74-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S)-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadien-1-ol
• 英文别名: (2S,3Z,6Z)-2-[tert-butyl(diphenyl)silyl]oxydodeca-3,6-dien-1-ol
• CAS: 173289-74-2
• 化学式: C₂₈H₄₀O₂Si
• 分子量: 436.71
• InChiKey: NCKKVNLDWRQEKF-BAMTXDRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadien-1-ol 在 4 A molecular sieve 、 sodium acetate 、 pyridinium chlorochromate 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 反应 4.58h， 生成 (10S)-methyl 10-<(tert-butyldiphenylsilyl)oxy>eicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoate
  参考文献：
  名称：

  Synthesis of 10(S)-Hydroxyeicosatetraenoic Acid:  A Novel Cytochrome P-450 Metabolite of Arachidonic Acid

  摘要：

  10(S)-(-)-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid methyl ester (2) was synthesized in eight steps starting from enantiomerically pure (Ri-glyceraldehyde acetonide. The 10(R)-(+)-enantiomer was prepared using an identical method except that the starting material was (S)-glyceraldehyde acetonide. By use of these authentic standards, it was possible to confirm that arachidonic acid was converted to a mixture of 10(S)-(-)-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid (1) and the 10(R)-(+)-enantiomer by phenobarbital-induced rat Liver microsomes.

  DOI：

  10.1021/jo951061w
• 作为产物：
  描述：

  [(3Z)-3-nonen-1-yl]triphenylphosphonium bromide 在 盐酸 、 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 、 lithium hexamethyldisilazane 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 39.5h， 生成 (2S)-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadien-1-ol
  参考文献：
  名称：

  Synthesis of 10(S)-Hydroxyeicosatetraenoic Acid:  A Novel Cytochrome P-450 Metabolite of Arachidonic Acid

  摘要：

  10(S)-(-)-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid methyl ester (2) was synthesized in eight steps starting from enantiomerically pure (Ri-glyceraldehyde acetonide. The 10(R)-(+)-enantiomer was prepared using an identical method except that the starting material was (S)-glyceraldehyde acetonide. By use of these authentic standards, it was possible to confirm that arachidonic acid was converted to a mixture of 10(S)-(-)-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid (1) and the 10(R)-(+)-enantiomer by phenobarbital-induced rat Liver microsomes.

  DOI：

  10.1021/jo951061w

文献信息

• Synthesis of 10(<i>S</i>)-Hydroxyeicosatetraenoic Acid:  A Novel Cytochrome P-450 Metabolite of Arachidonic Acid
  作者：Suresh N. Yeola、Samir A. Saleh、Alan R. Brash、Chandra Prakash、Douglass F. Taber、Ian A. Blair

  DOI：10.1021/jo951061w

  日期：1996.1.1

  10(S)-(-)-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid methyl ester (2) was synthesized in eight steps starting from enantiomerically pure (Ri-glyceraldehyde acetonide. The 10(R)-(+)-enantiomer was prepared using an identical method except that the starting material was (S)-glyceraldehyde acetonide. By use of these authentic standards, it was possible to confirm that arachidonic acid was converted to a mixture of 10(S)-(-)-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid (1) and the 10(R)-(+)-enantiomer by phenobarbital-induced rat Liver microsomes.