2-(N-benzylamino)-1-phenyl-1-propanol

• 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: 2-(N-benzylamino)-1-phenyl-1-propanol
• 英文别名: threo-2-benzylamino-1-phenylpropan-1-ol；(1RS,2RS)-2-benzylamino-1-phenyl-propan-1-ol；(+/-)-threo-2-Benzylamino-1-phenyl-propanol-(1)；(1RS:2RS)-2-Benzylamino-1-phenyl-propanol-(1)；(1S,2S)-2-(benzylamino)-1-phenylpropan-1-ol
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: BBPJQQNUQARKLX-XJKSGUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-(N-benzylamino)-1-phenyl-1-propanol 在 palladium on activated charcoal ammonium formate 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 (1S,2S)-2-甲氨基-1-苯基丙-1-醇
  参考文献：
  名称：

  Akamanchi; Ranbhan; Shah, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 4, p. 293 - 302

  摘要：

  DOI：
• 作为产物：
  描述：

  扁桃腈 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 乙醚 为溶剂， 反应 5.67h， 生成 2-(N-benzylamino)-1-phenyl-1-propanol
  参考文献：
  名称：

  Applications of Optically Active Aryl Cyanohydrins in the Synthesis of α-Hydroxy Aldehydes, α-Hydroxy Ketones and β-Hydroxy Amines

  摘要：

  从芳基醛中制备的高光学纯度氰基卤素可转化为 α-羟基醛、β-羟基酮和β-羟基胺，且无任何外消旋化现象，在新引入的立体中心处，赤式二对映异构体通常具有良好的立体选择性（90%）。

  DOI：

  10.1071/ch9902045

文献信息

• Diastereoselectivity in the Reduction of α-Oxy- and α-Amino-Substituted Acyclic Ketones by Polymethylhydrosiloxane
  作者：Durgesh Nadkarni、James Hallissey、Carlos Mojica

  DOI：10.1021/jo0260544

  日期：2003.1.1

  Diastereoselectivity in the reduction of alpha-alkoxy-, alpha-acyloxy-, and alpha-alkylamino-substituted ketones with polymethylhydrosiloxane (PMHS) in the presence of fluoride ion catalysis was investigated. High syn-selectivity was observed in the reduction of alpha-alkoxy, alpha-acyloxy, and alpha-dialkylamino ketones. Reduction of alpha-monoalkylamino ketone proceeded in anti-selective manner with

  研究了在氟离子催化下，用聚甲基氢硅氧烷（PMHS）还原α-烷氧基-，α-酰氧基-和α-烷基氨基取代的酮的非对映选择性。在还原α-烷氧基，α-酰氧基和α-二烷基氨基酮中观察到高的顺选择性。α-单烷基氨基酮的还原以中等选择性的反选择性方式进行。基于Felkin-Anh和Cram-chelate模型解释了观察到的选择性。
• Catalytic asymmetric addition of diethylzinc to aldehydes via chiral, non-racemic β-hydroxy and β-methoxy salicylhydrazone catalysts
  作者：Sucharita Banerjee、Gregory M. Ferrence、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2010.04.021

  日期：2010.4

  (1S,2S)-Pseudoephedrine and (1S,2S)-pseudonorephedrine have been converted to their corresponding hydrazines and condensed with either o-salicylaldehyde or 2-hydroxy-1-naphthaldehyde to afford a series of beta-hydroxysalicylhydrazones that have been employed in the asymmetric addition of diethylzinc to 2-naphthalclehyde in up to 56% ee In addition to this, the Ephedra hydrazines were also condensed with the o-hydroxyacetophenone derivative to form related hydrazones The use of these corresponding hydrazones in the asymmetric addition reaction with the diethylzinc did not yield improved enantioselectivines. Finally, Enders' hydrazine was used as a chiral scaffold for the synthesis of beta-methoxysalicylhydrazones. These compounds were employed in the asymmetric addition of diethylzinc to a variety of aromatic aldehydes with enantiomeric excesses as high as 68% ee (C) 2010 Elsevier Ltd All rights reserved

  (1S,2S)-伪麻黄碱和(1S,2S)-伪去甲麻黄碱已转化为相应的肼，并与邻-水杨醛或2-羟基-1-萘醛缩合，生成一系列β-羟基水杨醛肼，这些化合物在二乙基锌与2-萘甲醛的不对称加成反应中实现了高达56%的对映体过量。此外，麻黄碱肼还与邻-羟基乙酰苯酮衍生物缩合，形成相关肼。在这些对应肼与二乙基锌进行的不对称加成反应中，并未显著提高对映选择性。最后，Enders的肼被用作手性骨架，用于合成β-甲氧基水杨醛肼。这些化合物在多种芳香醛与二乙基锌的不对称加成反应中表现出高达68%的对映体过量。 © 2010 Elsevier Ltd. 保留所有权利。
• Diastereoselective reduction of α-aminoketones: Synthesis of <i>anti</i>- and <i>syn</i>-β-aminoalcohols
  作者：David S Fraser、Sheldon B Park、J Michael Chong

  DOI：10.1139/v03-165

  日期：2004.2.1

  Reduction of N-t-BOC-protected-N-alkyl α-aminoketones with LiEt₃BH or Li(s-Bu)₃BH furnishes protected syn-β-aminoalcohols with high selectivities. In contrast, removal of the BOC group followed by reduction of the aminoketone gives anti-β-aminoalcohols with variable selectivities. With aromatic ketones, selectivities are typically high while aliphatic ketones show mediocre to high selectivities depending on steric considerations.Key words: β-aminoalcohol, diastereoselective reduction.

  N-t-BOC保护的N-烷基α-氨基酮通过LiEt3BH或Li(s-Bu)3BH还原得到具有高选择性的保护的同型β-氨基醇。相反，去除BOC基团后再还原氨基酮会得到具有可变选择性的反型β-氨基醇。对于芳香酮，选择性通常很高，而脂肪族酮则根据立体位阻考虑显示出一般到高的选择性。关键词：β-氨基醇，对映选择性还原。
• Van Delft, Floris L.; Timmers, Cornelis M.; Van Der Marel, Gijs A., Synthesis, 1997, # 4, p. 450 - 454
  作者：Van Delft, Floris L.、Timmers, Cornelis M.、Van Der Marel, Gijs A.、Van Boom, Jacques H.

  DOI：——

  日期：——
• N-Pyridylmethylephedrine derivatives in the catalytic asymmetric addition of diethylzinc to aldehydes and diphenylphosphinoylimines
  作者：Sucharita Banerjee、Jonathan A. Groeper、Jean M. Standard、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2009.08.014

  日期：2009.9

  N-Pyridylmethyl-substituted Ephedra derivatives were synthesized by either direct alkylation or reductive alkylation of (1R,2S)-norephedrine, (1S,2S)-pseudo norephedrine, and (1R,2S)-ephedrine. These derivatives were then employed in asymmetric addition reactions with diethylzinc and aldehydes and diphenylphosphinoylimines. The use of the diastereomers from the Ephedra family allowed for a systematic evaluation of the contribution of the N-pyridylmethyl. (C) 2009 Elsevier Ltd. All rights reserved.