3-丙基-2-己烯酸甲酯 | 156572-89-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3-丙基-2-己烯酸甲酯
• 英文名称: 3-Propyl-2-hexenoic acid methyl ester
• 英文别名: 3-propyl-hex-2-enoic acid methyl ester；Methyl 3-propylhex-2-enoate
• CAS: 156572-89-3
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: KRIVRZWZACFKEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  6
• 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：

  3-丙基-2-己烯酸甲酯 在 palladium on barium sulfate lithium aluminium tetrahydride 、 氢气 作用下， 生成 3-丙基-1-己醇
  参考文献：
  名称：

  Taillandier; Benoit Guyod; Boucherle, European Journal of Medicinal Chemistry, 1975, vol. 10, # 5, p. 453 - 462

  摘要：

  DOI：
• 作为产物：
  描述：

  4-庚酮 、 三甲基膦酰基乙酸酯 在 lithium hydroxide 、 4 A molecular sieve 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以42%的产率得到3-丙基-2-己烯酸甲酯
  参考文献：
  名称：

  Horner-Wadsworth-Emmons羰基化合物烯化的新方法

  摘要：

  醛通过与氢氧化锂生成膦酸酯碳负离子而进行有效的E-立体选择性Horner-Wadsworth-Emmons烯化反应。在活化沸石的存在下，并通过缓慢添加碱，该反应可令人满意地用线性，环状，多官能酮进行。

  DOI：

  10.1016/s0040-4039(00)76914-0

文献信息

• A new procedure for Horner-Wadsworth-Emmons olefination of carbonyl compounds
  作者：Francesco Bonadies、Antonella Cardilli、Alessandra Lattanzi、Liliana R. Orelli、Arrigo Scettri

  DOI：10.1016/s0040-4039(00)76914-0

  日期：1994.5

  aldehydes undergo an efficient E-stereoselective Horner-Wadsworth-Emmons olefination by generation of phosphonate carbanion with lithium hydroxide. The reaction proceeds satisfactorily with linear, cyclic, polifunctional ketones in the presence of activated zeolites and and by the slow addition of the base.

  醛通过与氢氧化锂生成膦酸酯碳负离子而进行有效的E-立体选择性Horner-Wadsworth-Emmons烯化反应。在活化沸石的存在下，并通过缓慢添加碱，该反应可令人满意地用线性，环状，多官能酮进行。
• Bonadies Francesco, Cardilli Antonella, Lattanzi Alessandra, Orelli Lilia+, Tetrahedron Lett, 35 (1994) N 20, S 3383-3386
  作者：Bonadies Francesco, Cardilli Antonella, Lattanzi Alessandra, Orelli Lilia+

  DOI：——

  日期：——
• Enynones in Organic Synthesis. 6. Synthesis of Spirocyclic Methylenecyclopentenones and Analogs of the Methylenomycin Class of Antibiotics. Mechanism of Phenol Catalysis
  作者：Peter A. Jacobi、Lisa M. Armacost、Harry L. Brielmann、Reginald O. Cann、Joseph I. Kravitz、Michael J. Martinelli

  DOI：10.1021/jo00097a035

  日期：1994.9

  Spirocyclic methylenecyclopentenones of general structure 18 were prepared in a single step from bis-acetylenic alcohols 29 by a process involving initial oxy-Cope rearrangement to afford (Z)-enynones 30-Z followed by electrocyclic ring closure. Mechanistic studies indicate that the initial step leading from 30-Z to 18 is a thermal 1,5-prototropic shift to afford dienols which can cyclize by a symmetry-allowed (pi(4)s + sigma(2)s + pi(2)a) process. This last step is catalyzed by certain phenols having low oxidation potentials, most likely by a mechanism involving single electron transfer. Dramatic rate enhancements were also observed for the cyclization of simple enynones 37 to methylenecyclopentenones 39 upon catalysis with either a-tocopherol (vitamin E, 40) or tert-butylcatechol(41). Further enhancements in both rate and yield were obtained under conditions of photoassisted single electron transfer (PET), which afforded 39 in yields of 80-98%.
• Taillandier; Benoit Guyod; Boucherle, European Journal of Medicinal Chemistry, 1975, vol. 10, # 5, p. 453 - 462
  作者：Taillandier、Benoit Guyod、Boucherle、et al.

  DOI：——

  日期：——