(S)-(+)-2-benzylpentanoic acid | 58635-84-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-(+)-2-benzylpentanoic acid
• 英文别名: (S)-(+)-2-Benzylpentansaeure；(2S)-2-benzylpentanoic acid
• CAS: 58635-84-0
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: VXOWGOAKTRJAMM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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-benzylpentanoic acid 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 C₁₂H₁₅ClO
  参考文献：
  名称：

  The first organocatalyst-mediated enantioselective substitution of racemic iodoalkanes under radical conditions

  摘要：

  We have demonstrated for the first time an organocatalyst-mediated enantioselective substitution of racemic iodoalkanes at either a tertiary or a secondary stereogenic center leading to the corresponding optically active products with a tertiary or a quaternary allylated stereogenic center under radical conditions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.031
• 作为产物：
  描述：

  (2S)-2-benzyl-pentan-1-ol 在 Jones reagent 作用下， 以 丙酮 为溶剂， 以56%的产率得到(S)-(+)-2-benzylpentanoic acid
  参考文献：
  名称：

  The first organocatalyst-mediated enantioselective substitution of racemic iodoalkanes under radical conditions

  摘要：

  We have demonstrated for the first time an organocatalyst-mediated enantioselective substitution of racemic iodoalkanes at either a tertiary or a secondary stereogenic center leading to the corresponding optically active products with a tertiary or a quaternary allylated stereogenic center under radical conditions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.031

文献信息

• Remarkable Electronic and Steric Effects in the Nitrile Biotransformations for the Preparation of Enantiopure Functionalized Carboxylic Acids and Amides:  Implication for an Unsaturated Carbon−Carbon Bond Binding Domain of the Amidase
  作者：Ming Gao、De-Xian Wang、Qi-Yu Zheng、Zhi-Tang Huang、Mei-Xiang Wang

  DOI：10.1021/jo070581b

  日期：2007.8.1

  various functionalized racemic nitriles catalyzed by Rhodococcus erythropolis AJ270, a nitrile hydratase/amidase-containing microbial whole-cell catalyst, were studied. While the nitrile hydratase exhibits high catalytic efficiency but very low enantioselectivity against almost all nitrile substrates examined, the amidase is very sensitive toward the structure of the amides. The release of the steric crowdedness

  红球菌催化各种功能化外消旋腈的生物转化研究了含腈水合酶/酰胺酶的微生物全细胞催化剂AJ270。尽管腈水合酶显示出高的催化效率，但对几乎所有所检测的腈底物的对映选择性都非常低，但酰胺酶对酰胺的结构非常敏感。围绕基质立体中心的空间拥挤的释放以及向基质中引入不饱和碳-碳键导致反应速率的显着加速和对映选择性的显着提高。腈的生物转化提供了独特的，高产的合成路线，可合成被烯丙基，炔丙基，烯基或乙烯基官能化的高度对映体纯的羧酸和酰胺。H-喹啉-2-酮衍生物。
• Asymmetric synthesis of R and S .alpha.-alkylalkanoic acids from metalation and alkylation of chiral 2-oxazolines
  作者：A. I. Meyers、Gerald Knaus、Kazuyuki Kamata、Michael E. Ford

  DOI：10.1021/ja00418a041

  日期：1976.1
• The first organocatalyst-mediated enantioselective substitution of racemic iodoalkanes under radical conditions
  作者：Masatoshi Murakata、Toshiaki Jono、Tetsuya Shoji、Akiko Moriya、Yoko Shirai

  DOI：10.1016/j.tetasy.2008.10.031

  日期：2008.11

  We have demonstrated for the first time an organocatalyst-mediated enantioselective substitution of racemic iodoalkanes at either a tertiary or a secondary stereogenic center leading to the corresponding optically active products with a tertiary or a quaternary allylated stereogenic center under radical conditions. (C) 2008 Elsevier Ltd. All rights reserved.