(RS)-2-(N,N-dibenzylamino)-4-methylpentan-1-ol | 307532-07-6

• 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: (RS)-2-(N,N-dibenzylamino)-4-methylpentan-1-ol
• 英文别名: 2-(Dibenzylamino)-4-methyl-1-pentanol；2-(dibenzylamino)-4-methylpentan-1-ol
• CAS: 307532-07-6
• 化学式: C₂₀H₂₇NO
• 分子量: 297.44
• InChiKey: FWNZCCUWXPYXDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  (RS)-2-(N,N-dibenzylamino)-4-methylpentan-1-ol 在 吡啶 、 盐酸 、 正丁基锂 、 草酰氯 、 20 % Pd(OH)2/C 、 氢气 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， -78.0~90.0 ℃ 、506.66 kPa 条件下， 反应 105.5h， 生成 (S,S)-4-(N-acetylamino)-5-isobutylpyrrolidin-2-one
  参考文献：
  名称：

  Parallel Kinetic Resolution of Acyclic γ-Amino-α,β-unsaturated Esters: Application to the Asymmetric Synthesis of 4-Aminopyrrolidin-2-ones

  摘要：

  Conjugate addition of a 50:50 pseudoenantiomeric mixture of lithium (R)-N-benzyl-N(alpha-methylbenzyl)amide and lithium (S)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide to a range of racemic acyclic gamma-amino-alpha,beta-unsaturated esters (derived from the corresponding a-amino acids) effects their efficient parallel kinetic resolution, allowing the preparation of enantiopure beta,gamma-diamino esters. The beta,gamma-dlamlno ester products of these reactions are readily converted into the corresponding substituted 4-aminopyrrolidin-2-ones via N-debenzylation and cyclization.

  DOI：

  10.1021/ol203011u
• 作为产物：
  描述：

  DL-亮氨酸 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 (RS)-2-(N,N-dibenzylamino)-4-methylpentan-1-ol
  参考文献：
  名称：

  Parallel Kinetic Resolution of Acyclic γ-Amino-α,β-unsaturated Esters: Application to the Asymmetric Synthesis of 4-Aminopyrrolidin-2-ones

  摘要：

  Conjugate addition of a 50:50 pseudoenantiomeric mixture of lithium (R)-N-benzyl-N(alpha-methylbenzyl)amide and lithium (S)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide to a range of racemic acyclic gamma-amino-alpha,beta-unsaturated esters (derived from the corresponding a-amino acids) effects their efficient parallel kinetic resolution, allowing the preparation of enantiopure beta,gamma-diamino esters. The beta,gamma-dlamlno ester products of these reactions are readily converted into the corresponding substituted 4-aminopyrrolidin-2-ones via N-debenzylation and cyclization.

  DOI：

  10.1021/ol203011u

文献信息

• Stereoselective synthesis of (3R,4S)-statine utilising the iron acetyl complex [(η5-C5H5)Fe(CO)(PPh3)COMe] as a chiral acetate enolate equivalent.
  作者：Jason W.B. Cooke、Stephen G. Davies、Alan Naylor

  DOI：10.1016/s0040-4020(01)88019-4

  日期：1993.9

  Diethylaluminium enolates derived from the iron acetyl complex [(eta5-C5H5)Fe(CO)(PPh3)COMe] undergo highly diastereoselective aldol reactions with the homochiral aldehydes; N,N-dibenzyl valinal and N,N-dibenzyl leucinal. The diastereoselectivity is explained in terms of Masamune's model of double asymmetric indUCtion using the concept of matched and mismatched pairs. The matched pair aldol product arising from the reaction with N,N-dibenzyl leucinal is converted into the known gamma-amino-beta-hydroxy acid, (3R,4S)-statine.
• Parallel Kinetic Resolution of Acyclic γ-Amino-α,β-unsaturated Esters: Application to the Asymmetric Synthesis of 4-Aminopyrrolidin-2-ones
  作者：Stephen G. Davies、James A. Lee、Paul M. Roberts、James E. Thomson、Jingda Yin

  DOI：10.1021/ol203011u

  日期：2012.1.6

  Conjugate addition of a 50:50 pseudoenantiomeric mixture of lithium (R)-N-benzyl-N(alpha-methylbenzyl)amide and lithium (S)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide to a range of racemic acyclic gamma-amino-alpha,beta-unsaturated esters (derived from the corresponding a-amino acids) effects their efficient parallel kinetic resolution, allowing the preparation of enantiopure beta,gamma-diamino esters. The beta,gamma-dlamlno ester products of these reactions are readily converted into the corresponding substituted 4-aminopyrrolidin-2-ones via N-debenzylation and cyclization.