(R)-3-[(diphenylmethyl)amino]-1-phenylpropan-1-ol | 1452423-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-[(diphenylmethyl)amino]-1-phenylpropan-1-ol
• 英文别名: (1R)-3-(benzhydrylamino)-1-phenylpropan-1-ol
• CAS: 1452423-58-3
• 化学式: C₂₂H₂₃NO
• 分子量: 317.431
• InChiKey: PCMNZIFNHLRMMG-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (R)-3-[(diphenylmethyl)amino]-1-phenylpropan-1-ol 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成 3-(diphenylmethyl)-6-phenyl-1,3-oxazinane
  参考文献：
  名称：

  A Selective Transformation of Enals into Chiral γ-Amino Alcohols

  摘要：

  A one-pot synthesis of chiral amino alcohols from alpha,beta-unsaturated aldehydes is reported which circumvents competitive 1,2-versus 1,4-boryl addition, by means of using a sterically hindered amine-derived imine. In addition to the complete chemoselectivity, modification of the Cu(I) catalyst with readily available chiral diphosphines, such as (R)-DM-BINAP, gave the 1,4-boryl addition products with high levels of asymmetric induction.

  DOI：

  10.1021/ol4022029
• 作为产物：
  描述：

  N-[(3-phenylprop-2-en)methylene]-α-phenylbenzenemethanamine 在 (S)-联萘(3,5-二甲苯基)膦 、 联硼酸频那醇酯 、 copper(l) chloride 、 sodium t-butanolate 、 sodium tetrahydroborate 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以50%的产率得到(R)-3-[(diphenylmethyl)amino]-1-phenylpropan-1-ol
  参考文献：
  名称：

  A Selective Transformation of Enals into Chiral γ-Amino Alcohols

  摘要：

  A one-pot synthesis of chiral amino alcohols from alpha,beta-unsaturated aldehydes is reported which circumvents competitive 1,2-versus 1,4-boryl addition, by means of using a sterically hindered amine-derived imine. In addition to the complete chemoselectivity, modification of the Cu(I) catalyst with readily available chiral diphosphines, such as (R)-DM-BINAP, gave the 1,4-boryl addition products with high levels of asymmetric induction.

  DOI：

  10.1021/ol4022029

文献信息

• Preparation of Chiral γ-Secondary Amino Alcohols via Ni-Catalyzed Asymmetric Reductive Coupling of 2-Aza-butadiene with Aldehydes
  作者：Lei Yang、Weidong Shang、Li Zhang、Xia Zhang

  DOI：10.1021/acs.orglett.2c03090

  日期：2022.10.28

  The first Ni-catalyzed asymmetric reductive coupling of 2-aza-butadiene with aldehydes was achieved to synthesize chiral γ-secondary amino alcohols. This transformation features good enantioselectivity and tolerance to various functional groups, which may serve as a complementary method to previously reported noble-metal-catalyzed protocols. Through competition reaction, 2-aza-butadiene was proved

  实现了第一次 Ni 催化的 2-氮杂-丁二烯与醛的不对称还原偶联，以合成手性 γ-仲氨基醇。这种转化具有良好的对映选择性和对各种官能团的耐受性，可以作为先前报道的贵金属催化方案的补充方法。通过竞争反应，2-氮杂丁二烯被证明是比其全碳类似物 1,3-丁二烯更具反应性的偶联组分。值得注意的是，该反应产生 β-甲硅烷氧基亚胺，这是一种很难通过常规方法获得的氮杂醛醇型产物。
• A Selective Transformation of Enals into Chiral γ-Amino Alcohols
  作者：Adam D. J. Calow、Andrei S. Batsanov、Alba Pujol、Cristina Solé、Elena Fernández、Andrew Whiting

  DOI：10.1021/ol4022029

  日期：2013.9.20

  A one-pot synthesis of chiral amino alcohols from alpha,beta-unsaturated aldehydes is reported which circumvents competitive 1,2-versus 1,4-boryl addition, by means of using a sterically hindered amine-derived imine. In addition to the complete chemoselectivity, modification of the Cu(I) catalyst with readily available chiral diphosphines, such as (R)-DM-BINAP, gave the 1,4-boryl addition products with high levels of asymmetric induction.