(S)-(+)-2-cyano-2-methyl-3-phenylpropanoic acid | 27771-05-7

• 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-cyano-2-methyl-3-phenylpropanoic acid
• 英文别名: (2S)-2-cyano-2-methyl-3-phenylpropanoic acid；(S)-2-cyano-2-methyl-3-phenylpropanoic acid；(S)-3-phenyl-2-methyl-2-cyanopropanoic acid；(S)-2-cyano-2-methyl-3-phenyl-propionic acid；(S)-2-Cyan-2-methyl-3-phenyl-propionsaeure；(L)-3-phenyl-2-cyano-2-methyl-propionic acid
• CAS: 27771-05-7
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: XOKVFRWKAZRXOS-NSHDSACASA-N

物化性质

• 熔点：
  88 °C
• 沸点：
  358.8±30.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-cyano-2-methyl-3-phenylpropanoic acid 在 氯化亚砜 、 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 反应 12.67h， 生成 (2S)-2-cyano-2-methyl-3-phenylpropanoyl azide
  参考文献：
  名称：

  高效分离外消旋-2-氰基-2-甲基-3-苯基丙酸。大规模实验室规模对映体合成（S）-α-甲基苯丙氨酸的合适原料

  摘要：

  已经开发了由苯甲醛和氰基乙酸甲酯合成（S）-α-甲基苯丙氨酸的大规模实验室规模。合成是基于以下顺序：（i）外消旋2-氰基-2-甲基-3-苯基丙酸的制备，（ii）使用去甲麻黄碱通过结晶拆分对映异构体，以及（iii）开发有效的对映收敛合成（的小号从对映体纯（）-α甲基苯丙氨酸小号和（ - ）- [R）-2-氰基-2-甲基-3-苯基丙酸。实验程序的简单性，避免了低温反应，需要惰性气氛和柱色谱，再加上使用廉价且容易获得的试剂，使得该方法在合成上非常有吸引力。

  DOI：

  10.1016/s0957-4166(03)00450-6
• 作为产物：
  描述：

  2-苄基丙二腈 在 Rhodococcus sp. CGMCC 0497 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 (S)-(+)-2-cyano-2-methyl-3-phenylpropanoic acid
  参考文献：
  名称：

  Enantioselective biotransformation of α,α-disubstituted dinitriles to the corresponding 2-cyanoacetamides using Rhodococcus sp. CGMCC 0497

  摘要：

  A new application of nitrile-converting enzymes in the synthesis of optically active alpha,alpha-disubstituted-alpha-cyanoacetamides from alpha,alpha-disubstituted-malononitriles with whole cells of Rhodococcus sp. CGMCC 0497 is described. The products were obtained with enantiomeric excesses of up to >99%, and yields of up to 53%. They are very useful chiral intermediates especially for the synthesis of chiral alpha,alpha-disubstituted amino acids but have never been synthesized directly by chemical or enzymatic methods. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00456-7

文献信息

• Chiral 2-Cyanocinnamates in Conjugate Addition Asymmetric Enolate Trapping Reactions
  作者：Carlos Cativiela、Maria Dolores Diaz-De-Villegas、José Antonio Galvez

  DOI：10.1246/bcsj.65.1657

  日期：1992.6

  Chiral 2-cyanocinnamates react with L-selectride® to give an intermediate enolate which can be stereoselectively trapped with different halides to afford α-substituted phenylalanine precursors with excellent chemical yields and good diastereomeric excess.

  手性 2-氰基肉桂酸酯与 L-selectride® 反应生成中间体烯醇化物，该中间体可以被不同的卤化物立体选择性地捕获，以提供具有优异化学产率和良好非对映体过量的 α-取代苯丙氨酸前体。
• Highly enantioselective synthesis of α,α-disubstituted malonamic acids through asymmetric hydrolysis of dinitriles with Rhodococcus sp. CGMCC 0497Electronic supplementary information (ESI) available: full experimental details. See http://www.rsc.org/suppdata/cc/b2/b210743k/
  作者：Zhong-Liu Wu、Zu-Yi Li

  DOI：10.1039/b210743k

  日期：2003.1.23

  Highly enantioselective hydrolysis of α,α-disubstituted malononitriles by the strain Rhodococcus sp. CGMCC 0497 expressing both nitrile hydratase and amidase activity to give (R)-α,α-disubstituted malonamic acids which could be converted to valuable (R)- or (S)-α-alkylated amino acids are reported and the yields of the products are improved remarkably at a lower reaction temperature.

  报告了表达腈水解酶和酰胺酶活性的 Rhodococcus sp. CGMCC 0497 菌株对δ,δ-二取代丙二腈的高对映选择性水解，得到(R)-δ,δ-二取代丙二酸，这些丙二酸可转化为有价值的(R)-或(S)-δ-烷基化氨基酸。
• WO2007/88571
  申请人：——

  公开号：——

  公开（公告）日：——
• 749. The mechanism of the decarboxylation of substituted malonic acid derivatives
  作者：J. Kenyon、W. A. Ross

  DOI：10.1039/jr9510003407

  日期：——
• The effects of pneumoperitoneum and patient position on hemodynamics during laparoscopic cholecystectomy
  作者：R. Zuckerman、M. Gold、P. Jenkins、L.A. Rauscher、M. Jones、S. Heneghan

  DOI：10.1007/s004640080065

  日期：2001.6

  Background: The purpose of this study was to prospectively examine the combined effects of pneumoperitoneum and the reverse Trendelenberg position on cardiac hemodynamics during laparoscopic cholecystectomy.Methods: Thirty-nine patients undergoing laparoscopic cholecystectomy as performed by a single surgeon were en rolled in the study. Hemodynamic data were collected continuously using a transthoracic bioimpedance monitor. All patients were subjected to insufflation pressures of 15 mmHg. Data were examined using mixed analysis of variance (ANOVA).Results: Cardiac index fell 11% with induction of anesthesia (p < 0.05), with stroke volume decreasing 7.2% (p < 0.05). Insufflation caused significant decreases in stroke volume (SV) left ventricular end diastolic volume (LVEDV) but not cardiac index (CI). Placing the patients in the reverse Trendelenberg position caused no significant changes in these parameters. There were no significant differences between ASA (American Society of Anesthesiologists) classes I and IT patients when compared to ASA III patients.Conclusions: Patients undergoing laparoscopic cholecystectomy experience significant hemodynamic depression. The effect of general anesthesia is the most profound. Insufflation of the abdomen caused more mild hemodynamic effects in our study. The addition of a reverse Trendelenberg position did not alter the patient's hemodynamic status.