(E)-2-methyl-5-phenyl-2-hexenoic acid

• 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)-2-methyl-5-phenyl-2-hexenoic acid
• 英文别名: (E)-2-methyl-5-phenylhex-2-enoic acid
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: NWBDMYKOWUKZTH-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  惕格酸 、 (1-溴乙基)苯 在 N,N-二乙醇十二酰胺 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 (E)-2-methyl-5-phenyl-2-hexenoic acid 、 2-methyl-2-(1-phenylethyl)but-3-enoic acid
  参考文献：
  名称：

  Regiocontrol in Alkylation of Lithium Dienediolates of Unsaturated Carboxylic Acids

  摘要：

  用苄基卤化物对来自不饱和羧酸的二烯二醇盐进行烷基化，通常会导致区域异构体混合物的产生。然而，这可以通过对反应条件的适当改良来控制。因此，加入DMI主要导致α-区域异构体的生成，而加入12-冠-4则允许从相同反应物中获得作为主要产物的γ-区域异构体。

  DOI：

  10.1055/s-2001-9721

文献信息

• Regioselective Alkylation of Lithium Dienediolates of α,β-Unsaturated Carboxylic Acids
  作者：Eva M. Brun、Salvador Gil、Ramón Mestres、Margarita Parra

  DOI：10.1055/s-2000-6323

  日期：——

  Lithium carboxylic acids dienediolates are regioselectively alkylated at the α-carbon by reaction with tosylates derived from both primary and secondary alcohols. Both regio- and diastereoselectivity are improved when compared with those obtained in the corresponding alkylation with alkyl halides.

  锂羧酸二烯二醇化物在反应中与由伯醇和仲醇衍生的甲磺酸酯作用，能区域选择性地在α-碳位进行烷基化。与相应的烷基卤代物进行烷基化反应相比，无论是区域选择性还是立体选择性都有所提高。
• Enantioselective α-alkylation of unsaturated carboxylic acids using a chiral lithium amide
  作者：Eva M. Brun、Salvador Gil、Margarita Parra

  DOI：10.1016/s0957-4166(01)00152-5

  日期：2001.4

  The regio- and stereochemistry of the alkylation of dienediolates from unsaturated carboxylic acids with benzylic halides, which often results in mixtures of isomers, can be controlled by means of changes in the lithium amide, allowing the α-regioisomer to be obtained as the major diastereoisomer. In addition, when chiral amines are used, moderate enantiomeric excesses can be attained.

  来自不饱和羧酸与苄基卤化物的二烯二醇酯烷基化的区域和立体化学（通常会导致异构体的混合物）可以通过改变氨基锂来控制，从而可以将α-区域异构体作为主要的非对映异构体获得。另外，当使用手性胺时，可以获得中等的对映体过量。
• Lithium enediolates and dienediolates of carboxylic acids in synthesis: Alkylation with secondary halides
  作者：Eva M. Brun、Salvador Gil、Ramón Mestres、Margarita Parra

  DOI：10.1016/s0040-4020(98)00957-0

  日期：1998.12

  High yields in the alkylation of dianions of alpha,beta-unsaturated carboxylic acids with secondary halides can be obtained despite elimination reactions occurring. alpha-Regioselectivity for the alkylation of but-2-enoic acids (1-4) is seldom obtained. Although double bond stereoselectivity is higher than 99% for gamma-alkylated products, stereoselectivity is rather poor for most of the alpha-alkylated products. (C) 1998 Elsevier Science Ltd. AII rights reserved.
• INTRAOCULAR LENS COMPOSITIONS
  申请人：Teleon Holding B.V.

  公开号：EP3934705A1

  公开（公告）日：2022-01-12
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  公开号：US20130234084A1

  公开（公告）日：2013-09-12

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