(Z)-8,9-Dihydroxy-non-5-enoic acid methyl ester | 251311-87-2

• 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: (Z)-8,9-Dihydroxy-non-5-enoic acid methyl ester
• 英文别名: methyl (Z)-8,9-dihydroxynon-5-enoate
• CAS: 251311-87-2
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: XMLDAGVZSOKZFG-RQOWECAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (Z)-8,9-Dihydroxy-non-5-enoic acid methyl ester 在 lead(IV) acetate 、 sodium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 花生四烯酸甲酯
  参考文献：
  名称：

  A convenient strategy for the synthesis of β,γ-unsaturated aldehydes and acids. A construction of skipped dienes

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(99)01498-7
• 作为产物：
  描述：

  (Z)-8,9-Bis-triethylsilanyloxy-non-5-enoic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 以99%的产率得到(Z)-8,9-Dihydroxy-non-5-enoic acid methyl ester
  参考文献：
  名称：

  Silyl group deprotection by Pd/C/H2. A facile and selective method

  摘要：

  An easy, high yield, RT, short-reaction-time Pd/C hydrogenation of silyl groups is described. This includes TES, TPS, TBS, TBDMS, TIPS, and TBDPS. The relative selectivity of the process has been investigated and we can show, for example, that TES, TPS, TBS, and TBDMS removal can be performed in the presence of TIPS and TBDPS. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.145