(S)-3-phenyl-N-methylbutanamide | 136962-59-9

• 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)-3-phenyl-N-methylbutanamide
• 英文别名: (3S)-N-methyl-3-phenylbutanamide
• CAS: 136962-59-9
• 化学式: C₁₁H₁₅NO
• mdl: MFCD03348263
• 分子量: 177.246
• InChiKey: SPSRNBYKWRFJRB-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-phenylbut-2-enoyl chloride 在 sodium tetrahydroborate 、 (2E)-[(2S)-2-({[二甲基(2-甲基-2-丙基)硅烷基]氧基}甲基)-3,4-二氢-2H-吡咯-5-基][(5S)-5-({[二甲基(2-甲基-2-丙基)硅烷基]氧基}甲基)-2-吡咯烷基亚基]乙腈 、 cobalt(II) chloride 作用下， 以 四氢呋喃 、 乙醇 、 二乙二醇二甲醚 、 水 为溶剂， 反应 283.0h， 生成 (S)-3-phenyl-N-methylbutanamide
  参考文献：
  名称：

  Enantioselective conjugate reduction of α,β-unsaturated carboxamides with semicorrin cobalt catalysts

  摘要：

  Chiral semicorrin cobalt complexes, prepared in situ from cobalt(II) chloride and the free ligands, are efficient, highly enantioselective catalysts for the conjugate reduction of alpha,beta-unsaturated carboxamides with sodium borohydride. Enantiomeric excesses of up to 99 %, essentially quantitative yields, and high substrate/catalyst ratios (1 000 - 10 000:1) are attractive attributes of this catalytic process.

  DOI：

  10.1016/s0957-4166(00)86123-6

文献信息

• Asymmetric substitution: highly enantioselective substitutions induced at the carbanion of a racemic organolithium substrate by (-)-sparteine
  作者：Peter Beak、Hua Du

  DOI：10.1021/ja00059a062

  日期：1993.3
• Investigation of a broadly applicable chiral selector used in enantioselective chromatography (Whelk-O 1) as a chiral solvating agent for NMR determination of enantiomeric composition
  作者：Michael E. Koscho、William H. Pirkle

  DOI：10.1016/j.tetasy.2005.08.032

  日期：2005.10

  A chiral solvating agent (CSA) based on the chiral selector used in the Whelk-O I chiral stationary phase (CSP) was prepared and its scope evaluated. This chiral selector possesses a cleft flanked with aromatic groups and produces upfield chemical shifts for analytes. which are held in this cleft. The enantiomers of each of the Whelk-O I resolvable analytes surveyed show non-equivalent H-1 NMR spectra at room temperature with the addition of only 0.5 equiv of the CSA. Similar non-equivalence is sometimes noted for enantiomers, which do not resolve on this CSP. In such cases, it is apparent that a hydrogen bond acceptor is required and higher CSA to substrate ratios and/or lower temperatures may be needed if adequate resolution of enantiomeric signals is to be obtained. (c) 2005 Elsevier Ltd. All rights reserved.