(S)-(+)-2-phenylhexanoic acid | 21490-48-2

• 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: (S)-(+)-2-phenylhexanoic acid
• 英文别名: S-(+)-α-n-Butyl-phenyl-essigsaeure；(S)-n-Butyl-phenylessigsaeure；(S)-2-Phenyl-hexansaeure；(2S)-2-phenylhexanoic acid
• CAS: 21490-48-2
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: PGIOANNVJQQCDT-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-phenylhexanoic acid 、 甲基锂 在 乙醚 作用下， 生成 (3S)-3-phenylheptan-2-one
  参考文献：
  名称：

  The Effect of Ring Formation on Optical Rotatory Power. A Comparison of the Optical Rotations of 2-Phenylcyclopentanone and of Some Acyclic α-Phenyl Ketones

  摘要：

  DOI：

  10.1021/ja01611a056
• 作为产物：
  描述：

  2-phenylhexanoic acid 生成 (S)-(+)-2-phenylhexanoic acid
  参考文献：
  名称：

  旋光色散和绝对构型-XVII：α-烷基苯基乙酸

  摘要：

  对具有伯，仲和叔α-取代基的α-烷基苯基乙酸进行ORD和CD测量，与它们的非对映异构酰胺的气相色谱保留时间一致，从而得出结论，该系列的所有（+）-酸都具有相同的含义配置。

  DOI：

  10.1016/s0040-4020(01)90865-8

文献信息

• 10.1021/jacs.4c05217
  作者：Zhou, Li、Li, Liping、Zhang, Sudong、Kuang, Xiao-Kang、Zhou, You-Yun、Tang, Yong

  DOI：10.1021/jacs.4c05217

  日期：——

  The catalytic regio- and enantioselective hydrocarboxylation of alkenes with carbon dioxide is a straightforward strategy to construct enantioenriched α-chiral carboxylic acids but remains a big challenge. Herein we report the first example of catalytic highly enantio- and site-selective remote hydrocarboxylation of a wide range of readily available unactivated alkenes with abundant and renewable CO2

  烯烃与二氧化碳的催化区域和对映选择性加氢羧化是构建对映体富集的 α-手性羧酸的简单策略，但仍然是一个巨大的挑战。在此，我们报告了在 SaBOX/Ni 催化剂的温和条件下，利用丰富且可再生的 CO 2对各种容易获得的未活化烯烃进行高度对映和位点选择性远程加氢羧化的催化例子。这一成功的关键是利用手性 SaBOX 配体，它与镍结合，同时控制链行走和羧化的对映选择性。该方法以高产率和区域选择性和对映选择性直接提供一系列带有各种官能团的不同烷基链取代或苯并稠合的 α-手性羧酸。此外，通过从商业起始材料中简明合成抗血小板聚集药物（ R ）-吲哚布芬，证明了该方法的合成效用。
• Enantioselective biotransformations of racemic α-substituted phenylacetonitriles and phenylacetamides using Rhodococcus sp. AJ270
  作者：Mei-Xiang Wang、Gang Lu、Gai-Jiao Ji、Zhi-Tang Huang、Otto Meth-Cohn、John Colby

  DOI：10.1016/s0957-4166(00)00025-2

  日期：2000.3

  Rhodococcus sp. AJ270 is an efficient whole-cell system able to catalyze the stereoselective conversions of racemic alpha-substituted phenylacetonitriles and amides under very mild conditions into enantiopure carboxylic acids and derivatives. The nitrile hydratase involved generally has a broad substrate spectrum against phenylacetonitriles irrespective of the electronic nature of the alpha-substituent while the amidase is very sensitive to both the electronic and steric factors of the substituent of amides. The overall enantioselectivity of nitrile hydrolysis is mainly determined by the combination of selectivities of nitrile hydratase and of amidase, with the latter being a major contributor. The amidase has high S-enantiocontrol against amides while the nitrile hydratase exhibits low R-selectivity against nitriles. The scope and limitations of this enantioselective biotransformation process are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Pettersson; Willdeck, Arkiv foer Kemi, 1956, vol. 9, p. 333,334
  作者：Pettersson、Willdeck

  DOI：——

  日期：——
• SHIBATA, SAIZO;MATSUSHITA, HAJIME;KANEKO, HAJIME;NOGUCHI, MASAO;SABURI, M+, BULL. CHEM. SOC. JAP., 1982, 55, N 11, 3546-3551
  作者：SHIBATA, SAIZO、MATSUSHITA, HAJIME、KANEKO, HAJIME、NOGUCHI, MASAO、SABURI, M+

  DOI：——

  日期：——
• The Effect of Ring Formation on Optical Rotatory Power. A Comparison of the Optical Rotations of 2-Phenylcyclopentanone and of Some Acyclic α-Phenyl Ketones
  作者：Kurt Mislow、Charles L. Hamermesh

  DOI：10.1021/ja01611a056

  日期：1955.3