(E)-ethyl 2,5-dimethyl-3-hexenoate | 79918-82-4

• 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: (E)-ethyl 2,5-dimethyl-3-hexenoate
• 英文别名: 2,5-dimethyl-hex-3t-enoic acid ethyl ester；2,5-dimethyl-hex-3-enoic acid ethyl ester；2,5-Dimethyl-hex-3t-ensaeure-aethylester；2,5-Dimethyl-hex-3-ensaeure-aethylester；ethyl (E)-2,5-dimethylhex-3-enoate
• CAS: 79918-82-4
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: CQFBKYVEQWZSQM-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (E)-ethyl 2,5-dimethyl-3-hexenoate 生成 异丁醛
  参考文献：
  名称：

  Cope; Hofmann, Journal of the American Chemical Society, 1941, vol. 63, p. 3458

  摘要：

  DOI：
• 作为产物：
  描述：

  异戊醛 在 碘 、 phosphorus pentoxide 、 锌 、 苯 作用下， 生成 (E)-ethyl 2,5-dimethyl-3-hexenoate
  参考文献：
  名称：

  Crombie et al., Journal of the Chemical Society, 1957, p. 2754,2759

  摘要：

  DOI：

文献信息

• Palladium(0)-catalyzed carbonylation of allyl phosphates and allyl acetates. Selective synthesis of β,γ-unsaturated esters
  作者：Shun-Ichi Murahashi、Yasushi Imada、Yuki Taniguchi、Shin-ya Higashiura

  DOI：10.1016/s0040-4039(00)80648-6

  日期：1988.1

  Palladium catalyzed carbonylations of allyl phosphates and allyl acetates give β,γ-unsaturated esters efficiently. The latter reaction requires bromide ion as a co-catalyst.

  钯催化的烯丙基磷酸酯和乙酸烯丙酯的羰基化反应可有效地生成β，γ-不饱和酯。后一反应需要溴离子作为助催化剂。
• Stereochemistry of deconjugative alkylation of ester dienolates. Stereospecific total synthesis of the litsenolides
  作者：Andrew S. Kende、Bruce H. Toder

  DOI：10.1021/jo00340a041

  日期：1982.1
• Palladium(0)-catalyzed alkoxycarbonylation of allyl phosphates and acetates
  作者：Shunichi Murahashi、Yasushi Imada、Yuki Taniguchi、Shinya Higashiura

  DOI：10.1021/jo00058a040

  日期：1993.3

  Palladium-catalyzed alkoxycarbonylation of allyl phosphates under CO (1 atm) at 50-degrees-C proceeds highly efficiently to give the corresponding beta,gamma-unsaturated esters. The carbonylation of geranyl phosphate ((E)-11) under CO (1 atm) at 50-degrees-C gave ethyl ester of homogeranic acid ((E)-12) stereoselectively. The carbonylation takes place at the least substituted allylic positions with inversion of configuration. Typically, the methoxycarbonylation of cis-5-(methoxycarbonyl)-2-cyclohexen-1-yl phosphate (cis-16) gave trans-dimethyl 2-cyclohexene-1,5-dicarboxylate (trans-17) selectively. Alkoxycarbonylation of allyl acetates is performed for the first time in the presence of a catalytic amount of bromide ion. The reaction can be rationalized by assuming the mechanism which involves oxidative addition of palladium(0) species to allyl acetates to give pi-allylpalladium acetate, fast ligand exchange of the acetate with bromide, insertion of carbon monoxide to give acylpalladium species, and alkoxylation.
• Murahashi Shun-Ichi, Imada Yasushi, Taniguchi Yuki, Higashiura Shinya, J. Org. Chem, 58 (1993) N 6, S 1538-1545
  作者：Murahashi Shun-Ichi, Imada Yasushi, Taniguchi Yuki, Higashiura Shinya

  DOI：——

  日期：——
• MURAHASHI, SHUN-ICHI;IMADA, YASUSHI;TANIQUCHI, YUKI;HIGASHIURA, SHIN-YA, TETRAHEDRON LETT., 29,(1988) N 39, C. 4945-4948
  作者：MURAHASHI, SHUN-ICHI、IMADA, YASUSHI、TANIQUCHI, YUKI、HIGASHIURA, SHIN-YA

  DOI：——

  日期：——