(Z,Z)-4-deca-1,4-dien-1-yl-2,2-dimethyl-1,3-dioxolane | 173289-70-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z,Z)-4-deca-1,4-dien-1-yl-2,2-dimethyl-1,3-dioxolane
• 英文别名: (4S)-4-[(1Z,4Z)-deca-1,4-dienyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 173289-70-8
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: GLJMPNDAPITFBD-ROLKAOPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z,Z)-4-deca-1,4-dien-1-yl-2,2-dimethyl-1,3-dioxolane 在 盐酸 、 4-二甲氨基吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (2S)-1-<(tert-butyldimethylsilyl)oxy>-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadiene
  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 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 lithium hexamethyldisilazane 作用下， 生成 (Z,Z)-4-deca-1,4-dien-1-yl-2,2-dimethyl-1,3-dioxolane
  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.