11-bromo-5(Z),8(Z)-undecadienoic acid | 125010-74-4

• 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: 11-bromo-5(Z),8(Z)-undecadienoic acid
• 英文别名: (5Z,8Z)-11-bromoundeca-5,8-dienoic acid
• CAS: 125010-74-4
• 化学式: C₁₁H₁₇BrO₂
• 分子量: 261.159
• InChiKey: FSEOCLOEMBULRN-OVYZBVKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  14.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  11-bromo-5(Z),8(Z)-undecadienoic acid 生成 (10-methoxycarbonyldeca-3,6-cis,cis-dienyl)-triphenylphosphonium bromide
  参考文献：
  名称：

  The total synthesis of 15(S)-HPETE (hydroperoxyeicosatetraenoic acid)

  摘要：

  The total synthesis of 15(S)-HPETE in enantiomerically pure form is achieved through C=C bond formation in the presence of a masked hydroperoxide. Selective reduction of a peracid in the presence of a hydroperoxide affords a mild method for removal of an HPETE methyl ester.

  DOI：

  10.1021/jo00033a006
• 作为产物：
  描述：

  7-(tetrahydro-2H-pyran-2-yloxy)hept-2-yn-1-ol 在 copper(I) bromide dimethylsulfide complex 、 nickel diacetate 、 乙二胺 咪唑 、 sodium tetrahydroborate 、 四溴化碳 、 乙基溴化镁 、 氢气 、 碘 、 铬酸 、 对甲苯磺酸 、 三苯基膦 作用下， 以 甲醇 为溶剂， 生成 11-bromo-5(Z),8(Z)-undecadienoic acid
  参考文献：
  名称：

  The total synthesis of 15(S)-HPETE (hydroperoxyeicosatetraenoic acid)

  摘要：

  The total synthesis of 15(S)-HPETE in enantiomerically pure form is achieved through C=C bond formation in the presence of a masked hydroperoxide. Selective reduction of a peracid in the presence of a hydroperoxide affords a mild method for removal of an HPETE methyl ester.

  DOI：

  10.1021/jo00033a006

文献信息

• Mosset, Paul; Gree, Rene; Falck, J. R., Synthetic Communications, 1989, vol. 19, # 3and4, p. 645 - 658
  作者：Mosset, Paul、Gree, Rene、Falck, J. R.

  DOI：——

  日期：——
• A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE
  作者：Patrick Dussault、In Quen Lee

  DOI：10.1021/jo00106a037

  日期：1995.1

  A new synthetic approach to enantiomerically pure hydroperoxyeicosatetraenoic acids (HPETEs) is described in which the tetraene skeleton is assembled through chemoselective olefination of a protected hydroperoxy aldehyde. Soybean lipoxygenase-mediated dioxygenation of both natural and unnatural fats produces hydroperoxy dienes in high enantiomeric excess; the observed regioselectivity supports a revised hypothesis for substrate specificity. Protection of the diene hydroperoxides as peroxy ketals is followed by regioselective ozonolysis to afford enantiomerically pure 4-peroxy 2,3-enals which undergo olefination to produce peroxytetraenoates. Removal of the monoperoxy ketal and the methyl ester affords enantiomerically pure HPETEs. The generality of the strategy is illustrated with the first chemical synthesis of 5(S)-HPETE.
• MOSSET, PAUL;GREE, RENE;FALCK, J. R., SYNTH. COMMUN., 19,(1989) N-4, C. 645-658
  作者：MOSSET, PAUL、GREE, RENE、FALCK, J. R.

  DOI：——

  日期：——