(R)-(-)-3-methyl-2-phenylbutyramide | 13490-79-4

• 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: (R)-(-)-3-methyl-2-phenylbutyramide
• 英文别名: (R)-3-methyl-2-phenylbutyramide；(R)-(-)-α-Isopropyl-phenylacetamid；(R)-(-)-α-Isopropylphenylacetamid；(2R)-3-methyl-2-phenylbutanamide
• CAS: 13490-79-4
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: TZWZKDIRNLJDQG-SNVBAGLBSA-N

物化性质

• 熔点：
  138-140 °C
• 沸点：
  322.5±21.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(-)-3-methyl-2-phenylbutyramide 在 劳森试剂 、 吡啶 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 24.03h， 生成 (S)-5-(2-methyl-1-phenylpropyl)-3H-1,2,4-dithiazol-3-one
  参考文献：
  名称：

  Synthesis of chiral disulfides: potential reagents for enantioselective sulfurization

  摘要：

  Synthesis of chiral phosphorothioates for use as antisense oligonucleotides might benefit from the use of chiral disulfides. This paper reports the synthesis of chiral analogs of phenylacetyl disulfide and of 5-methyl-3H-1,2,4-dithiazol-3-one from the same set of 2-arylalkanoic acids. The X-ray crystal structures of the disulfides derived from (R) and [S]-2-phenylpropanoic acid establish the stereochemistry and the helicity of these materials, and density functional theory calculations suggest that the high specific rotations can be due to preferred retention of this helicity in solution. Chiral HPLC showed that the final products were formed with enantiomeric purities from 86.1% to99.9%. [image omitted].

  DOI：

  10.1080/17415993.2011.580346
• 作为产物：
  描述：

  (2R)-3-methyl-2-phenylbutanoyl chloride 在 ammonium hydroxide 、 水 作用下， 以 苯 为溶剂， 生成 (R)-(-)-3-methyl-2-phenylbutyramide
  参考文献：
  名称：

  Synthesis of chiral disulfides: potential reagents for enantioselective sulfurization

  摘要：

  Synthesis of chiral phosphorothioates for use as antisense oligonucleotides might benefit from the use of chiral disulfides. This paper reports the synthesis of chiral analogs of phenylacetyl disulfide and of 5-methyl-3H-1,2,4-dithiazol-3-one from the same set of 2-arylalkanoic acids. The X-ray crystal structures of the disulfides derived from (R) and [S]-2-phenylpropanoic acid establish the stereochemistry and the helicity of these materials, and density functional theory calculations suggest that the high specific rotations can be due to preferred retention of this helicity in solution. Chiral HPLC showed that the final products were formed with enantiomeric purities from 86.1% to99.9%. [image omitted].

  DOI：

  10.1080/17415993.2011.580346

文献信息

• Exploring the Crystal Landscape of 3-Methyl-2-phenylbutyramide: Crystallization of Metastable Racemic Forms from the Stable Conglomerate
  作者：U. B. Rao Khandavilli、Declan P. Gavin、Anita R. Maguire、Michael Nolan、Simon E. Lawrence

  DOI：10.1021/acs.cgd.8b00348

  日期：2018.6.6

  In the solid state, (±)-3-methyl-2-phenylbutyramide 1 spontaneously resolves into a conglomerate (Form I) that crystallizes in a racemic form (Form II) upon melting followed by vapor crystallization, a rarely reported phenomenon. An additional racemic polymorph, Form III, has been characterized, and the thermodynamic relationship between the three forms established by a variety of computational and experimental

  在固态下，（±）-3-甲基-2-苯基丁酰胺1自发地分解为团聚体（形式I），该团聚体在熔融后结晶为外消旋形式（形式II），随后发生气相结晶，这是很少报道的现象。表征了另一种外消旋多晶型物形式III，并通过多种计算和实验方法（包括研磨，浆液结晶和晶种技术）建立了这三种形式之间的热力学关系。外消旋形式II和III是亚稳和容易地转换为更稳定的砾岩，的不同多晶型物的晶型I的密度泛函理论计算1所表明的对映异构体1（- [R ＆小号）比两种外消旋形式都更稳定。
• 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.
• Resolution and configuration of .alpha.-substituted phenylacetic acids
  作者：Colin Aaron、David L. Dull、Joel L. Schmiegel、David Jaeger、Yoko Ohashi、Harry S. Mosher

  DOI：10.1021/jo01284a035

  日期：1967.9
• Cervinka,O. et al., Collection of Czechoslovak Chemical Communications, 1970, vol. 35, p. 724 - 726
  作者：Cervinka,O. et al.

  DOI：——

  日期：——
• Cervinka,O. et al., Zeitschrift fur Chemie, 1969, vol. 9, p. 267 - 268
  作者：Cervinka,O. et al.

  DOI：——

  日期：——