(2E,12Z,15Z)-1-hydroxyheneicosa-2,12,15-trien-4-one | 344770-43-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,12Z,15Z)-1-hydroxyheneicosa-2,12,15-trien-4-one
• 英文别名: (2E,12Z,15Z)-1-hydroxyhenicosa-2,12,15-trien-4-one
• CAS: 344770-43-0
• 化学式: C₂₁H₃₆O₂
• 分子量: 320.516
• InChiKey: HYSAQRFMZWHDTN-BJFGNJKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,12Z,15Z)-1-hydroxyheneicosa-2,12,15-trien-4-one 、 苯硼酸 在 4 A molecular sieve 、 二异丙胺 作用下， 以 甲苯 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  Enantioselective, Organocatalytic Oxy-Michael Addition to γ/δ-Hydroxy-α,β-enones:  Boronate-Amine Complexes as Chiral Hydroxide Synthons

  摘要：

  An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha, beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.

  DOI：

  10.1021/ja076802c
• 作为产物：
  描述：

  乙醇醛二聚体 、 dimethyl (10Z,13Z)-2-oxononadeca-10,13-dienylphosphonate 在 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以51%的产率得到(2E,12Z,15Z)-1-hydroxyheneicosa-2,12,15-trien-4-one
  参考文献：
  名称：

  Enantioselective, Organocatalytic Oxy-Michael Addition to γ/δ-Hydroxy-α,β-enones:  Boronate-Amine Complexes as Chiral Hydroxide Synthons

  摘要：

  An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha, beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.

  DOI：

  10.1021/ja076802c

文献信息

• Novel hepatic disorder suppressant
  申请人：Arimoto Yasushi

  公开号：US20050163877A1

  公开（公告）日：2005-07-28

  A hepatic disorder suppressant comprising extracts having hepatic disorder suppressing effect as effective ingredients, wherein the extracts is obtained by extracting an avocado plant and/or a processed product thereof with an organic solvent is disclosed.

  本发明公开了一种肝功能紊乱抑制剂，其有效成分包括具有肝功能紊乱抑制作用的提取物，其中的提取物是通过用有机溶剂提取牛油果植物和/或其加工产品获得的。
• US7081480B2
  申请人：——

  公开号：US7081480B2

  公开（公告）日：2006-07-25
• US7101913B2
  申请人：——

  公开号：US7101913B2

  公开（公告）日：2006-09-05
• Enantioselective, Organocatalytic Oxy-Michael Addition to γ/δ-Hydroxy-α,β-enones:  Boronate-Amine Complexes as Chiral Hydroxide Synthons
  作者：De Run Li、Andiappan Murugan、J. R. Falck

  DOI：10.1021/ja076802c

  日期：2008.1.1

  An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha, beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.