(S)-2-methyl-1-<<2'-(hydroxymethyl)pyrrolidinyl>carbonyl>benzene | 115512-57-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-methyl-1-<<2'-(hydroxymethyl)pyrrolidinyl>carbonyl>benzene
• 英文别名: (S)-N-(2-methylbenzoyl)-prolinol；(S)-2-methyl-1-{[2'-(hydroxymethyl)pyrrolidinyl]carbonyl}benzene；[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-(2-methylphenyl)methanone
• CAS: 115512-57-7
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: CXZNPQGZFHPMBP-NSHDSACASA-N

物化性质

• 熔点：
  66-69 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  397.1±25.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-methyl-1-<<2'-(hydroxymethyl)pyrrolidinyl>carbonyl>benzene 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (S)-2-methyl-1-<(2'-formylpyrrolidinyl)carbonyl>benzene
  参考文献：
  名称：

  An enantioselective method for reductive alkylation of aromatic carboxylic acid derivatives. Examination of the factors that provide stereoselectivity

  摘要：

  DOI：

  10.1021/ja00231a038
• 作为产物：
  描述：

  邻甲基苯甲酰氯 、 L-脯氨醇 在 三乙胺 作用下， 以 氯仿 为溶剂， 以81%的产率得到(S)-2-methyl-1-<<2'-(hydroxymethyl)pyrrolidinyl>carbonyl>benzene
  参考文献：
  名称：

  Influence of the nature of chiral auxiliaries on the diastereoselective hydrogenation of ortho-substituted benzoic acid derivatives

  摘要：

  The diastereoselective hydrogenation of o-toluic acid or o-methoxy benzoic acid covalently bound to different chiral auxiliaries was performed on Rh and Ru supported catalysts. The cis-isomers were formed predominantly, with a diastereoselectivity largely influenced by the structure of the chiral inductor and the steric hindrance brought for the preferential adsorption of one face of the aromatic substrate. The effect of the functional group on the proline auxiliary (alcohol or ester groups susceptible to modify the anchoring of the aromatic substrate) was weak. Hydrogenolysis occurred rather extensively with the methoxy benzoic acid and constituted the most important hydrogenation pathway on Rh/C. The presence of the C=O group in the pyroglutamic acid methyl ester is a determining factor for obtaining good diastereoselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00112-9

文献信息

• Stereospecific Palladium-Catalyzed Decarboxylative C(sp³)C(sp²) Coupling of 2,5-Cyclohexadiene-1-carboxylic Acid Derivatives with Aryl Iodides
  作者：Chih-Ming Chou、Indranil Chatterjee、Armido Studer

  DOI：10.1002/anie.201103450

  日期：2011.9.5

  Walk on the same side! The title reaction occurs by means of highly stereospecific 1,3‐metal migration. The starting carboxylic acids are readily prepared by Birch reduction, and the developed protocol provides an efficient route to enantiomerically pure 5‐arylated‐1,3‐cyclohexadiene derivatives (see scheme).

  走在同一边！标题反应是通过高度立体定向的1,3-金属迁移发生的。可以通过Birch还原轻松制备起始羧酸，并且开发的方案为对映体纯的5芳基化1,3-环己二烯衍生物提供了一条有效途径（参见方案）。
• SCHULTZ, ARTHUR G.;MACIELAG, MARK;SUNDARARAMAN, PADMANABHAN;TAVERAS, ARTH+, J. AMER. CHEM. SOC., 110,(1988) N 23, C. 7828-7841
  作者：SCHULTZ, ARTHUR G.、MACIELAG, MARK、SUNDARARAMAN, PADMANABHAN、TAVERAS, ARTH+

  DOI：——

  日期：——
• Influence of the nature of chiral auxiliaries on the diastereoselective hydrogenation of ortho-substituted benzoic acid derivatives
  作者：Michèle Besson、Pierre Gallezot、Samuel Neto、Catherine Pinel

  DOI：10.1016/s0957-4166(00)00112-9

  日期：2000.5

  The diastereoselective hydrogenation of o-toluic acid or o-methoxy benzoic acid covalently bound to different chiral auxiliaries was performed on Rh and Ru supported catalysts. The cis-isomers were formed predominantly, with a diastereoselectivity largely influenced by the structure of the chiral inductor and the steric hindrance brought for the preferential adsorption of one face of the aromatic substrate. The effect of the functional group on the proline auxiliary (alcohol or ester groups susceptible to modify the anchoring of the aromatic substrate) was weak. Hydrogenolysis occurred rather extensively with the methoxy benzoic acid and constituted the most important hydrogenation pathway on Rh/C. The presence of the C=O group in the pyroglutamic acid methyl ester is a determining factor for obtaining good diastereoselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• An enantioselective method for reductive alkylation of aromatic carboxylic acid derivatives. Examination of the factors that provide stereoselectivity
  作者：Arthur G. Schultz、Mark. Macielag、Padmanabhan. Sundararaman、Arthur G. Taveras、Martha. Welch

  DOI：10.1021/ja00231a038

  日期：1988.11