(5Z,8Z)-10-Bromo-deca-5,8-dienoic acid methyl ester | 785822-64-2

• 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: (5Z,8Z)-10-Bromo-deca-5,8-dienoic acid methyl ester
• 英文别名: methyl (5Z,8Z)-10-bromodeca-5,8-dienoate
• CAS: 785822-64-2
• 化学式: C₁₁H₁₇BrO₂
• 分子量: 261.159
• InChiKey: PWCMGQRJHFESAR-RMFUBFLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5Z,8Z)-10-Bromo-deca-5,8-dienoic acid methyl ester 在 chromium dichloride 、 sodium periodate 、 溶剂黄146 、 nickel dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 (5Z,8Z,13E)-(11S,12S,15S)-15-(tert-Butyl-dimethyl-silanyloxy)-12-hydroxy-11-(pyrrolidine-1-carbothioyloxy)-icosa-5,8,13-trienoic acid methyl ester
  参考文献：
  名称：

  Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilator

  摘要：

  The four stereoisomers of the endothelial-derived vasorelaxant 11,12,15(S)-trihydroxyeicosatrienoic acid [1, 11,12,15(S)THETA] were prepared by a triply convergent, asymmetric route that exploited the stereospecific, copper mediated cross-coupling of alpha,beta-dialkoxystannanes with organic electrophiles and the utility of dialkylthionocarbarnates as orthogonal alcohol protective groups. Only 11(R),12(S),15(S)-THETA was comparable to natural material by HPLC, GC/MS, and in vitro bioassay. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.019
• 作为产物：
  描述：

  10-(tert-Butyl-diphenyl-silanyloxy)-deca-5,8-diynoic acid methyl ester 在 P-2 nickel sodium tetrahydroborate 、 四溴化碳 、 camphor-10-sulfonic acid 、 氢气 、 nickel diacetate 、 乙二胺 、 三苯基膦 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 (5Z,8Z)-10-Bromo-deca-5,8-dienoic acid methyl ester
  参考文献：
  名称：

  Total synthesis of the cytochrome P-450 epoxygenase metabolites 5(R),6(S)-, 5(S),6(R)-, and 14(R),15(S)-epoxyeicosatrienoic acid (EET) and hydration products 5(R),6(R)- and 14(R),15(R)-dihydroxyeicosatrienoic acid (DHET)

  摘要：

  DOI：

  10.1021/ja00304a048

文献信息

• Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilator
  作者：J.R. Falck、Deb Barma、Suchismita Mohapatra、A. Bandyopadhyay、Komandla Malla Reddy、Jianjun Qi、William Campbell

  DOI：10.1016/j.bmcl.2004.07.019

  日期：2004.10

  The four stereoisomers of the endothelial-derived vasorelaxant 11,12,15(S)-trihydroxyeicosatrienoic acid [1, 11,12,15(S)THETA] were prepared by a triply convergent, asymmetric route that exploited the stereospecific, copper mediated cross-coupling of alpha,beta-dialkoxystannanes with organic electrophiles and the utility of dialkylthionocarbarnates as orthogonal alcohol protective groups. Only 11(R),12(S),15(S)-THETA was comparable to natural material by HPLC, GC/MS, and in vitro bioassay. (C) 2004 Elsevier Ltd. All rights reserved.
• Total synthesis of the cytochrome P-450 epoxygenase metabolites 5(R),6(S)-, 5(S),6(R)-, and 14(R),15(S)-epoxyeicosatrienoic acid (EET) and hydration products 5(R),6(R)- and 14(R),15(R)-dihydroxyeicosatrienoic acid (DHET)
  作者：Christine A. Moustakis、Jacques Viala、Jorge Capdevila、J. R. Falck

  DOI：10.1021/ja00304a048

  日期：1985.9