methyl (6S,13R)-6,13-dihydroxy-2E,4E,8E-tetradecatrienoate | 211751-74-5

• 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: methyl (6S,13R)-6,13-dihydroxy-2E,4E,8E-tetradecatrienoate
• 英文别名: methyl (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate；methyl (2E,4E,6S,8E,13R)-6,13-dihydroxytetradeca-2,4,8-trienoate
• CAS: 211751-74-5
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: SJYBMSQTXHDPLR-SYALTKAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 、 methyl (6S,13R)-6,13-dihydroxy-2E,4E,8E-tetradecatrienoate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2E,4E,8E)-(6S,13R)-6,13-Bis-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-tetradeca-2,4,8-trienoic acid methyl ester
  参考文献：
  名称：

  A hydroxytetradecatrienoic acid from Mycosphaerella rubella

  摘要：

  Investigations on the acidic fractions from extracts of a culture of Mycosphaerella rubella led to the isolation of a new unsaturated dihydroxy acid, 6,13-dihydraxytetradeca-2,4,8-trienoic acid, and two of its derivatives, which are probably artifacts. Their structures were determined on the basis of H-1 and C-13 NMR evidence. The absolute configuration of the chiral centres of the new acid was elucidated using the modified Mosher's method. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00027-2
• 作为产物：
  描述：

  methyl (6S,13R)-6,13-di-(tert-butyldiphenylsilyloxy)tetradeca-(2E,4E,8E)-trienoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以87%的产率得到methyl (6S,13R)-6,13-dihydroxy-2E,4E,8E-tetradecatrienoate
  参考文献：
  名称：

  A chemoenzymatic asymmetric synthesis of methyl (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate, a component of Mycosphaerella rubella

  摘要：

  The first asymmetric synthesis of (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate has been developed. The key steps of the synthesis were the use of an efficient lipase-catalyzed acylation, a chiral template-driven enantiocontrolled allylation for introducing the stereogenic centers, and a cross-meta thesis for controlling the C-8 olefin geometry. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.04.004

文献信息

• A chemoenzymatic asymmetric synthesis of methyl (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate, a component of Mycosphaerella rubella
  作者：Anubha Sharma、Sunita Gamre、Subrata Chattopadhyay

  DOI：10.1016/j.tetasy.2009.04.004

  日期：2009.6

  The first asymmetric synthesis of (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate has been developed. The key steps of the synthesis were the use of an efficient lipase-catalyzed acylation, a chiral template-driven enantiocontrolled allylation for introducing the stereogenic centers, and a cross-meta thesis for controlling the C-8 olefin geometry. (C) 2009 Elsevier Ltd. All rights reserved.
• A hydroxytetradecatrienoic acid from Mycosphaerella rubella
  作者：Alberto Arnone、Gianluca Nasini、Orso Vajna de Pava

  DOI：10.1016/s0031-9422(98)00027-2

  日期：1998.6

  Investigations on the acidic fractions from extracts of a culture of Mycosphaerella rubella led to the isolation of a new unsaturated dihydroxy acid, 6,13-dihydraxytetradeca-2,4,8-trienoic acid, and two of its derivatives, which are probably artifacts. Their structures were determined on the basis of H-1 and C-13 NMR evidence. The absolute configuration of the chiral centres of the new acid was elucidated using the modified Mosher's method. (C) 1998 Elsevier Science Ltd. All rights reserved.