methyl (E)-5-undecenoate | 67270-84-2

• 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: methyl (E)-5-undecenoate
• 英文别名: 5-Hendecensaeuremethylester；methyl (E)-undec-5-enoate
• CAS: 67270-84-2
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: VDDLADIPQFIPEC-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  methyl (E)-5-undecenoate 在 氢氧化钾 、 乙醇 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (Z)-5-undecenoic acid
  参考文献：
  名称：

  Eutectic potassium-sodium-aluminum chloride as a mild catalyst for ene reactions: simple synthesis of the sex pheromone from Douglas fir tussock moth

  摘要：

  DOI：

  10.1021/jo00416a036
• 作为产物：
  描述：

  (E)-undec-5-enoic acid 、 甲醇 生成 methyl (E)-5-undecenoate
  参考文献：
  名称：

  EWEISS, N. F., J. UNIV. KUWEIT(SCI.), 1982, 9, N 2, 229-235

  摘要：

  DOI：

文献信息

• Simple methods for the syntheses of (E)-4- and (E)-5-alkenoic acids by the SN2′ type reactions of γ-vinyl-γ-butyrolactone and δ-vinyl-δ-valerolactone with organocopper reagents
  作者：Tamotsu Fujisawa、Toshio Sato、Masatoshi Kawashima、Kouichi Naruse、Kouichi Tamai

  DOI：10.1016/s0040-4039(00)87676-5

  日期：1982.1
• Enzymes in organic synthesis. 27. Lipase-Catalyzed Synthesis of (5R,6S)-6-Acetoxyalkan-5-olides - homologues of the mosquito oviposition attractant pheromone
  作者：B. Henkel、A. Kunath、Hans Schick

  DOI：10.1002/prac.19973390176

  日期：——

  Sixteen homologous (5R*,6S*)-6-hydroxyalkan-5-olides rac-5 and their acetoxy derivatives rac-6 were synthesized from the corresponding methyl (Z)-alk-5-enoates 3 by osmium(VIII) oxide catalyzed cis-hydroxylation to the dihydroxy esters rac-4 and hydrolysis of these esters followed by lactonization. Pancreatin-catalyzed lactonization of the dihydroxy esters rac-4 afforded enantiomerically enriched hydroxy lactones ent-5, five of which were obtained enantiomerically pure by recrystallization. Acetylation of the 6-hydroxyalkan-5-olides rac-5 by vinyl acetate catalyzed by the lipase SP 526 provided enantiomerically enriched 6-acetoxyalkan-5-olides 6 with an enantiomeric excess of more than 90% in nine cases. These compounds are known as mosquito oviposition attractant pheromone (6h) or its homologues.
• FUJISAWA, TAMOTSU;SATO, TOSHIO;KAWASHIMA, MASATOSHI;NARUSE, KOUICHI;TAMAI+, TETRAHEDRON LETT., 1982, 23, N 35, 3583-3586
  作者：FUJISAWA, TAMOTSU、SATO, TOSHIO、KAWASHIMA, MASATOSHI、NARUSE, KOUICHI、TAMAI+

  DOI：——

  日期：——
• Eutectic potassium-sodium-aluminum chloride as a mild catalyst for ene reactions: simple synthesis of the sex pheromone from Douglas fir tussock moth
  作者：Bjorn Akermark、Anders Ljungqvist

  DOI：10.1021/jo00416a036

  日期：1978.10
• EWEISS, N. F., J. UNIV. KUWEIT(SCI.), 1982, 9, N 2, 229-235
  作者：EWEISS, N. F.

  DOI：——

  日期：——