(Z)-dec-4-en-1,2-diol | 89616-41-1

• 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: (Z)-dec-4-en-1,2-diol
• 英文别名: (2RS,4Z)-4-decen-1,2-diol；(Z)-dec-4-ene-1,2-diol
• CAS: 89616-41-1
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: WBMVOLPFVJEVDJ-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-dec-4-en-1,2-diol 在 lead(IV) acetate 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-壬-3-烯醛
  参考文献：
  名称：

  Irreversible inhibition of prostaglandin and leukotriene biosynthesis from arachidonic acid by 11,12-dehydro- and 5,6-dehydroarachidonic acids, respectively

  摘要：

  DOI：

  10.1021/ja00370a058
• 作为产物：
  描述：

  2,2-dimethyl-4-[(Z)-oct-2-enyl]-1,3-dioxolane 在 溶剂黄146 作用下， 反应 20.0h， 以92%的产率得到(Z)-dec-4-en-1,2-diol
  参考文献：
  名称：

  Synthesis of the Eight Enantiomerically Pure Diastereomers of the 12-F₂-Isoprostanes

  摘要：

  Syntheses of the eight enantiomerically pure diastereomers of the 12-F-2-isoprostanes (4-11) are described. The key steps included rhodium-mediated intramolecular cyclopropanation and enzymatic resolution of the racemic diol 12.

  DOI：

  10.1021/ja020816v

文献信息

• Absolute configuration of C(1)C(5) fragment of AAL-toxin: Conformationally rigid acyclic aminotriol moiety
  作者：Hideaki Oikawa、Isamu Matsuda、Akitami Ichihara、Keisuke Kohmoto

  DOI：10.1016/0040-4039(94)88029-8

  日期：1994.2

  Degradation of AAL-toxin 1 a host-specific phytotoxin and synthesis of model aminotriol 7a - 7d allowed us to determine the absolute configuration of C(1)C(5) fragment as 2S, 4S and 5R. Unusually rigid conformation of this acyclic fragment was also discussed.

  AAL-毒素降解1宿主特异性植物毒素和模型aminotriol的合成图7a - 7D使我们能够确定C的绝对构型（1）C（5）片段作为2小号，4小号和5 - [R 。还讨论了该无环片段的异常刚性构象。
• An efficient preparation of stereospecific β-hydroxy nitriles
  作者：Sheila H. Jacobo、Mustafa Adiyaman、Chih-Tsung Chang、Nam-In Kang、William S. Powell、Joshua Rokach

  DOI：10.1016/j.tetlet.2004.10.174

  日期：2005.1

  The cyanide-ring opening of thionocarbonates with NaCN in DMF and TBACN in THF is described. This reaction occurred regioselectively to afford β-hydroxy nitrile with preserved stereochemistry of the hydroxy group in high yield.

  描述了在DMF中用NaCN和在THF中用TBACN对硫代碳酸酯的氰化物环的开环。该反应选择性地发生，从而以高收率提供了具有保留的羟基立体化学的β-羟基腈。
• A convenient strategy for the synthesis of β,γ-unsaturated aldehydes and acids. A construction of skipped dienes
  作者：Goutam Saha、Manas K. Basu、Seongjin Kim、Young-Ju Jung、Yurdanur Adiyaman、Mustafa Adiyaman、William S. Powell、Garret A. FitzGerald、Joshua Rokach

  DOI：10.1016/s0040-4039(99)01498-7

  日期：1999.10

  A novel strategy is described for the synthesis of beta,gamma-unsaturated aldehydes which are the useful synthons for the synthesis of arachidonic acid and other eicosanoid products. These beta,gamma-unsaturated aldehydes have been used in the total synthesis of arachidonic acid. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Absolute configuration of main chain of AAL-toxins.
  作者：Hideaki Oikawa、Isamu Matsuda、Takashi Kagawa、Akitami Ichihara、Keisuke Kohmoto

  DOI：10.1016/s0040-4020(01)89343-1

  日期：1994.1

  AAL-toxins TA(1) 1 and TA(2) 2, host-specific toxins produced by Alternaria alternata, were degraded to 2-methylbutanol, 3-methylnonan-1,9-diol and N-protected 4-aminobutan-1-3-diol, which were further converted to (R)-MTPA esters. These esters were correlated with synthesis samples by comparison of their 500 MHz H-1-NMR spectra. The remaining stereocenters were determined by the comparison of H-1-NMR spectra of 6a and 7 derived from 1 and 2 with those of synthetic model compounds. These data conclude that AAL-toxins possess 2S, 4S, 5R, 11S, 13S, 14R and 15R configurations.
• Stereochemical course of 5-lipoxygenation of arachidonate by rat basophil leukemic cell (RBL-1) and potato enzymes
  作者：E. J. Corey、Peter T. Lansbury

  DOI：10.1021/ja00350a059

  日期：1983.6