(Z)-6-Phenyl-hex-4-enoic acid | 84565-04-8

• 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)-6-Phenyl-hex-4-enoic acid
• CAS: 84565-04-8
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: NQAGOKSFEAOCKC-DJWKRKHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-ethoxy-5-vinyltetrahydrofurane 以 四氢呋喃 为溶剂， 生成 (Z)-6-Phenyl-hex-4-enoic acid
  参考文献：
  名称：

  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

  摘要：

  DOI：

  10.1016/s0040-4039(00)87676-5

文献信息

• Unravelling the olefin cross metathesis on solid support. Factors affecting the reaction outcome
  作者：Andrés A. Poeylaut-Palena、Ernesto G. Mata

  DOI：10.1039/c004729e

  日期：——

  Olefin cross metathesis on solid support under a variety of conditions is described. A comprehensive analysis considering diverse factors governing the reaction outcome gives a series of patterns for the application of this useful methodology in organic synthesis. If the intrasite reaction is not possible, homodimerization of the soluble olefin is crucial. When the homodimer is less reactive than its monomer, reaction outcome depends on the homodimerization rate, which, in turn, depends on the precatalyst used and the reaction conditions. If the site–site interaction is a feasible process, the cross metathesis product is obtained exclusively when the newly-formed double bond is resilient to further metathetic events. Taking into account these considerations, we have demonstrated that excellent results in terms of cross metathesis coupling can be obtained under the optimized conditions, and that microwave irradiation is also an interesting alternative for the development of a practical and energy-efficient cross metathesis on solid support.

  描述了在多种条件下固体支持上的烯烃交叉致密反应。对影响反应结果的各种因素进行综合分析，提供了一系列模式，便于在有机合成中应用这一有用的方法论。如果站点内反应不可行，溶解烯烃的同聚化至关重要。当同聚物的反应性低于其单体时，反应结果取决于同聚化速率，而这又取决于所使用的前催化剂和反应条件。如果站点间相互作用是可行的过程，当新形成的双键对进一步的致密反应具有抵抗力时，将独占性地获得交叉致密产物。考虑到这些因素，我们展示了在优化条件下可以获得交叉致密耦合的优秀结果，并且微波辐射也是开发实用且节能的固体支持交叉致密反应的一个有趣选择。
• NEW SYNTHETIC METHOD OF (Z)-4-ALKENOIC ACIDS USING RING-OPENING REACTION OF (Z)-4-HEXENOLIDE WITH ORGANOCOPPER REAGENT
  作者：Tamotsu Fujisawa、Kazuto Umezu、Masatoshi Kawashima

  DOI：10.1246/cl.1984.1795

  日期：1984.10.5

  (Z)-4-Hexenolide reacted regioselectively with diorganocuprates to give (Z)-4-alkenoic acids in high yields. Synthetic utility was demonstrated by the convenient synthesis of cis-jasmone.

  (Z)-4-己烯内酯与二有机铜酸盐发生区域选择性反应，以高产率得到 (Z)-4-链烯酸。顺式茉莉酮的方便合成证明了合成效用。