(1S,2R,3R)-3-amino-2-methyl-1,3-diphenylpropan-1-ol | 1315331-52-2

• 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: (1S,2R,3R)-3-amino-2-methyl-1,3-diphenylpropan-1-ol
• CAS: 1315331-52-2
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: ZUZICNWIVVTAPD-WQVCFCJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 盐酸 、 sodium tetrahydroborate 、 二异丁基氢化铝 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 (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

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。
• Synthesis of 1,3-Amino Alcohols from 2-Aza-1,3-dienes by Reduction of 5,6-Dihydro-2<i>H</i>-1,3-oxazines
  作者：José Barluenga、Jesús Joglar、Francisco J. González、Santos Fustero、Carl Krüger、Y. -H. Tsay

  DOI：10.1055/s-1991-26473

  日期：——

  5,6-Dihydro-2H-1,3-oxazines 3, prepared from 2-aza-1,3-dienes 4, react with sodium in 2-propanol, giving tetrahydro-2H-1,3-oxazines 5. The acid hydrolysis of 5 leads to 1,3-amino alcohols 6 with three stereocenters. The reduction of 3 with lithium aluminum hydride affords N-alkyl derivatives of 1,3-amino alcohols 7 with four stereocenters. The stereochemistry of these compounds was established by X-ray crystallography of (4S*,5S*,6R*)-5-methyl -4,6-diphenyl-3-[(1R*)-1-phenylpropyl]tetrahydro-2H-1,3-oxazine (8).

  5,6-二氢-2H-1,3-恶嗪3，由2-氮杂-1,3-二烯4制备，与钠在2-丙醇中反应，得到四氢-2H-1,3-恶嗪5。 5的水解产生具有三个立构中心的1,3-氨基醇6。用氢化铝锂还原3得到具有四个立构中心的1,3-氨基醇的N-烷基衍生物7。这些化合物的立体化学是通过(4S*,5S*,6R*)-5-甲基-4,6-二苯基-3-[(1R*)-1-苯基丙基]四氢-2H-的X射线晶体学确定的1,3-恶嗪(8)。
• 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
• Reduction of 5,6-dihydro-2H-1,3-oxazines. A simple approach to 1,3-aminoalcohols from 2-aza-1,3-dienes
  作者：José Barluenga、Jesús Joglar、Francisco J. González、Santos Fustero

  DOI：10.1016/s0040-4039(00)99635-7

  日期：1989.1
• BARLUENGA, J.;JOGLAR, J.;GONZALEZ, F. J.;FUETERO, S., TETRAHEDRON LETT., 30,(1989) N5, C. 2001-2004
  作者：BARLUENGA, J.、JOGLAR, J.、GONZALEZ, F. J.、FUETERO, S.

  DOI：——

  日期：——