(2S,3R)-3-amino-2-methyl-1,3-diphenylpropan-1-one | 1315331-24-8

• 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: (2S,3R)-3-amino-2-methyl-1,3-diphenylpropan-1-one
• CAS: 1315331-24-8
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: CQSQVRNPRBRKRN-SWLSCSKDSA-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：

  (2S,3R)-3-amino-2-methyl-1,3-diphenylpropan-1-one 在 sodium 、 异丙醇 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 20.0h， 生成 5-methyl-4,6-diphenyltetrahydro-1,3-oxazine
  参考文献：
  名称：

  Diastereoselective synthesis of .gamma.-amino alcohols with three chiral centers by reduction of .beta.-amino ketones and derivatives

  摘要：

  DOI：

  10.1021/jo00221a018
• 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 (2S,3R)-3-amino-2-methyl-1,3-diphenylpropan-1-one
  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

• A Tandem Isomerization-Mannich Reaction for the Enantioselective Synthesis of β-Amino Ketones and β-Amino Alcohols with Applications as Key Intermediates for ent-Nikkomycins and ent-Funebrine
  作者：Hai Thuong Cao、Thierry Roisnel、Alain Valleix、René Grée

  DOI：10.1002/ejoc.201100352

  日期：2011.7

  P-Amino ketones, with a primary amino group, are easily obtained in good yields and excellent enantioselectivities through a short sequence that involves, as a key step, a tandem isomerization-Mannich reaction from allylic alcohols with N-tert-butanesulfinimines. This method was used for the enantioselective synthesis of corresponding β-amino alcohols and also for key intermediates in the preparation

  具有伯氨基的对氨基酮很容易通过短序列以良好的产率和出色的对映选择性获得，该序列涉及作为关键步骤的烯丙醇与 N-叔丁烷亚磺亚胺的串联异构化-曼尼希反应。该方法用于相应β-氨基醇的对映选择性合成，也用于制备ent-nikkomycins或ent-funebrine的关键中间体。
• 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
• BARLUENGA, J.;OLANO, B.;FUSTERO, S., J. ORG. CHEM., 1983, 48, N 13, 2255-2259
  作者：BARLUENGA, J.、OLANO, B.、FUSTERO, S.

  DOI：——

  日期：——
• 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.
• Diastereoselective synthesis of .gamma.-amino alcohols with three chiral centers by reduction of .beta.-amino ketones and derivatives
  作者：Jose Barluenga、Bernardo Olano、Santos Fustero

  DOI：10.1021/jo00221a018

  日期：1985.10