(2R*,3R*)-3-Amino-2-methyl-1,3-diphenyl-1-propanone | 85356-30-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2R*,3R*)-3-Amino-2-methyl-1,3-diphenyl-1-propanone
• 英文别名: (2S,3S)-3-amino-2-methyl-1,3-diphenylpropan-1-one
• CAS: 85356-30-5
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: CQSQVRNPRBRKRN-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R*,3R*)-3-Amino-2-methyl-1,3-diphenyl-1-propanone 在 二异丁基氢化铝 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以72%的产率得到(1S,2R,3R)-3-amino-2-methyl-1,3-diphenylpropan-1-ol
  参考文献：
  名称：

  Stereoselective synthesis of 1,3-amino alcohols and 1,3-amino ketones

  摘要：

  Syn,anti-N-Alkyl-1,3-amino alcohols 2 with three chiral centers are synthesized with high stereoselectively by reduction of the corresponding anti-N-acylamino ketones 1 with LiAlH4/TiCl4. The intermediate N-acylamino alcohols 3 can be isolated when DIBALH/ZnCl2 is used instead of the prior reducing system. Cyclic models are proposed to explain the steric course of the reaction in both cases. On the other hand, hydrolysis of tetrahydropyrimidines 8 with 1 N HCl at 25-degrees-C leads to syn-1,3-amino ketones 9 with high stereoselectivity. Several reducing reagents and conditions are tested in the conversion of syn-9 into the subsequent 1,3-amino alcohols. DIBALH/ZnCl2 gives the best results in the last reaction leading to syn,syn-1,3-amino alcohols 10 as practically a single diastereoisomer.

  DOI：

  10.1021/jo00030a033
• 作为产物：
  描述：

  3-imino-1,3,N-triphenyl-2-methylprop-1-enylamine 在 盐酸 、 sodium tetrahydroborate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 (2R*,3R*)-3-Amino-2-methyl-1,3-diphenyl-1-propanone
  参考文献：
  名称：

  Stereoselective synthesis of 1,3-amino alcohols and 1,3-amino ketones

  摘要：

  Syn,anti-N-Alkyl-1,3-amino alcohols 2 with three chiral centers are synthesized with high stereoselectively by reduction of the corresponding anti-N-acylamino ketones 1 with LiAlH4/TiCl4. The intermediate N-acylamino alcohols 3 can be isolated when DIBALH/ZnCl2 is used instead of the prior reducing system. Cyclic models are proposed to explain the steric course of the reaction in both cases. On the other hand, hydrolysis of tetrahydropyrimidines 8 with 1 N HCl at 25-degrees-C leads to syn-1,3-amino ketones 9 with high stereoselectivity. Several reducing reagents and conditions are tested in the conversion of syn-9 into the subsequent 1,3-amino alcohols. DIBALH/ZnCl2 gives the best results in the last reaction leading to syn,syn-1,3-amino alcohols 10 as practically a single diastereoisomer.

  DOI：

  10.1021/jo00030a033

文献信息

• Reduction of 1,3-diimines. A new and general method of synthesis of .gamma.-diamines, .beta.-amino ketones, and derivatives with two and three chiral centers
  作者：Jose Barluenga、Bernardo Olano、Santos Fustero

  DOI：10.1021/jo00161a022

  日期：1983.7
• Diastereospecific Synthesis of Enantiomerically Pure Polysubstituted Azetidines from 1,3-Amino Alcohols with Three Chiral Centers
  作者：José Barluenga、Félix Fernández-Marí、Argimiro L. Viado、Enrique Aguilar、Bernardo Olano

  DOI：10.1021/jo960494b

  日期：1996.1.1
• Stereoselective synthesis of 1,3-amino alcohols and 1,3-amino ketones
  作者：Jose Barluenga、Enrique Aguilar、Santos Fustero、Bernardo Olano、Argimiro L. Viado

  DOI：10.1021/jo00030a033

  日期：1992.2

  Syn,anti-N-Alkyl-1,3-amino alcohols 2 with three chiral centers are synthesized with high stereoselectively by reduction of the corresponding anti-N-acylamino ketones 1 with LiAlH4/TiCl4. The intermediate N-acylamino alcohols 3 can be isolated when DIBALH/ZnCl2 is used instead of the prior reducing system. Cyclic models are proposed to explain the steric course of the reaction in both cases. On the other hand, hydrolysis of tetrahydropyrimidines 8 with 1 N HCl at 25-degrees-C leads to syn-1,3-amino ketones 9 with high stereoselectivity. Several reducing reagents and conditions are tested in the conversion of syn-9 into the subsequent 1,3-amino alcohols. DIBALH/ZnCl2 gives the best results in the last reaction leading to syn,syn-1,3-amino alcohols 10 as practically a single diastereoisomer.