(Z)-N,3-dimethyl-5-phenylpent-2-enamide | 76757-07-8

• 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: (Z)-N,3-dimethyl-5-phenylpent-2-enamide
• CAS: 76757-07-8
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: HNHKVFSRAWPJTO-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-N,3-dimethyl-5-phenylpent-2-enamide 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 乙醇 、 二乙二醇二甲醚 为溶剂， 反应 68.0h， 以96%的产率得到(S)-N,3-dimethyl-5-phenylpentanamide
  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
• 作为产物：
  描述：

  (E)-3-methyl-5-phenylpent-2-enoic acid 在 草酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (Z)-N,3-dimethyl-5-phenylpent-2-enamide
  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

• Cobalt(II)-Azabis(oxazoline)-Catalyzed Conjugate Reduction of ?,?-Unsaturated Carbonyl Compounds
  作者：Christian Geiger、Peter Kreitmeier、Oliver Reiser

  DOI：10.1002/adsc.200404295

  日期：2005.2

  Azabis(oxazolines) prove to be superior ligands for the enantioselective, cobalt(II)-catalyzed conjugate reduction of α,β-unsaturated carbonyl compounds with sodium borohydride. β-Trisubstituted α,β-unsaturated esters and amides as well as γ-butenolides are readily converted to their corresponding saturated counterparts with enantioselectivities up to 97% ee.

  氮杂双（恶唑啉）被证明是对映选择性，钴（II）催化的硼氢化钠对α，β-不饱和羰基化合物的共轭还原反应的优良配体。β-三取代的α，β-不饱和酯和酰胺以及γ-丁烯内酯很容易转化为相应的饱和对映体，对映选择性高达97％ee。
• Metalated unsaturated amides. Regio- and stereoselective .gamma.-alkylation
  作者：M. Majewski、G. B. Mpango、M. T. Thomas、A. Wu、V. Snieckus

  DOI：10.1021/jo00323a012

  日期：1981.5
• MAJEWSKI M.; MPANGO G. B.; THOMAS M. T.; WU A.; SNIECKUS V., J. ORG. CHEM., 1981, 46, NO 10, 2029-2045
  作者：MAJEWSKI M.、 MPANGO G. B.、 THOMAS M. T.、 WU A.、 SNIECKUS V.

  DOI：——

  日期：——
• Enantioselective conjugate reduction of α,β-unsaturated carboxamides with semicorrin cobalt catalysts
  作者：Peter von Matt、Andreas Pfaltz

  DOI：10.1016/s0957-4166(00)86123-6

  日期：1991.1

  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.