(2S)-2-Benzylideneamino-3-phenylpropan-1-ol | 99306-88-4

• 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: (2S)-2-Benzylideneamino-3-phenylpropan-1-ol
• 英文别名: (S)-2-(Benzylideneamino)-3-phenylpropan-1-ol；(2S)-2-(benzylideneamino)-3-phenylpropan-1-ol
• CAS: 99306-88-4
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: XPAUYOLNAAYWDN-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-Benzylideneamino-3-phenylpropan-1-ol 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 68.0h， 生成 (S)-N-benzyl-4-benzyl-3-aza-1,5-pentanediol
  参考文献：
  名称：

  β-氨基醇的高度对映选择性合成：催化形式

  摘要：

  通过使用催化量的三氟乙酸酐，可以实现β-氨基醇的高度对映选择性重排。

  DOI：

  10.1021/jo071028x
• 作为产物：
  描述：

  L-苯丙氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium tetrahydroborate 、 碘 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 19.0h， 生成 (2S)-2-Benzylideneamino-3-phenylpropan-1-ol
  参考文献：
  名称：

  Synthesis of novel C2-symmetric and pseudo C2-symmetric based diols, epoxides and dideoxy derivatives of HIV protease inhibitors

  摘要：

  The Julia's olefination reaction between the sulfone derivative (10) and the aldehyde (13) (both obtained from L-phenylalanine) followed by debenzylation led to the formation (2S,5S,3E)-2,5-bis-[( I,l-dimethyl ethoxy)-carbonyl]amino-l ,6-diphenylhex-3-ene (4a). Similarly (2S,5S,3E)-2,5-bis- [(1,1-dimethylethoxy)-carbonyl]amino- 1-phenyl-6-(p-methoxy)phenylhex-3-ene (4b) was also synthesised from the sulfone (10) and L-tyrosine derived aldehyde (21). These novel intermediates (4a and 4b) were subjected to epoxidation, hydrogenation, hydroboration-oxidation and dihydroxylation reactions. These modifications resulted in the synthesis of known and unknown, C-2-symmetric and pseudo-C-2-symmetric diamino-epoxides, dideoxy derivatives, diols and deoxy diols based HIV protease inhibitors. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00160-9

文献信息

• An iterative approach to novel polyamines via nucleophilic ring-opening of aziridinium ions with β-amino alcohols
  作者：Christopher McKay、Robert J. Wilson、Christopher M. Rayner

  DOI：10.1039/b401447b

  日期：——

  An iterative procedure for the synthesis of a novel class of synthetic polyamines has been developed, utilising the regioselective ring-opening of aziridinium ion intermediates; facile N-allyl deprotection of intermediate polyamines allows the rapid construction of high molecular weight, stereochemically defined compounds in a convergent manner.

  利用叠氮鎓离子中间体的区域选择性开环，已经开发出一种用于合成一类新的合成多胺的迭代方法。中间体多胺的N-烯丙基轻松脱保护可以以收敛的方式快速构建高分子量，立体化学定义的化合物。
• Asymmetric reduction of acetophenone using lithium aluminium hydride modified with some novel amino alcohol Schiff bases
  作者：Recep Tümerdem、Giray Topal、Yılmaz Turgut

  DOI：10.1016/j.tetasy.2004.12.020

  日期：2005.2

  chiral Schiff bases have been prepared in good yields from various carbonyl groups and two 2-amino alcohols. LiAlH4 was treated with different equivalents of the Schiff bases. Enantioselective reduction of acetophenone is achieved in high chemical yield (up to 93%) with moderate enantiomeric excess (up to 22%) by use of the new reducing agents.

  已经从各种羰基和两种2-氨基醇中以高收率制备了一些新的手性席夫碱。用不同当量的席夫碱处理LiAlH 4。通过使用新的还原剂，苯乙酮的对映选择性还原可实现高化学收率（最高93％）和适度的对映体过量（最高22％）。
• N-Alkyl oxazolidines as stereocontrol elements in asymmetric Diels–Alder cycloadditions of 9-substituted anthracene derivatives
  作者：Harry Adams、Ramadan A. Bawa、Simon Jones

  DOI：10.1039/b610055d

  日期：——

  Chiral 9-oxazolidinyl anthracene derivatives have been prepared as single diastereoisomers by condensation of 9-anthraldehyde with the appropriate N-alkyl amino alcohol. Asymmetric Diels–Alder cycloadditions of these with N-methyl maleimide proceeds in good yield and in good diastereoselectivity, the sense of which may be controlled by judicious choice of the N-alkyl group.

  通过 9-蒽醛与适当的 N-烷基氨基醇缩合，制备出了手性 9-噁唑烷基蒽衍生物单非对映异构体。这些衍生物与 N-甲基马来酰亚胺的不对称 DielsâAlder 环加成反应具有良好的产率和非对映选择性。
• Substituent effects in ring-chain tautomerism of the condensation products of non-racemic 1,2-aminoalcohols with aromatic aldehydes
  作者：Márta Juhász、László Lázár、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2011.11.011

  日期：2011.12

  at 300 K as three-component (ringcis-open-ringtrans) tautomeric mixtures. The electronic effects of the 2-aryl substituents on the tautomeric equilibria were described by the Hammett equation. Good correlations were found between the equilibrium constants and the Hammett–Brown parameter (σ+) of the substituent X on the 2-phenyl group.

  （S）-2-氨基-2-苯基乙醇或（S）-2-氨基-3-苯基丙醇与取代的苯甲醛在甲醇或水中的缩合生成结晶产物，证明该产物在300 K的CDCl 3中以3 -组分（环顺式-开环反式）互变异构混合物。通过哈米特方程描述了2-芳基取代基对互变异构体平衡的电子效应。在平衡常数与2-苯基上的取代基X的Hammett-Brown参数（σ +）之间发现了良好的相关性。
• Rearrangement of N-alkyl 1,2-amino alcohols. Synthesis of (S)-toliprolol and (S)-propanolol
  作者：Béranger Duthion、Thomas-Xavier Métro、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1016/j.tet.2009.05.072

  日期：2009.8

  N-alkyl 1,2-amino alcohols were rearranged stereospecifically by using TFAA/Et3N. This rearrangement has been used to synthesize N-isopropyl-3-(aryloxy)-2-hydroxypropylamines, beta-adrenergic blocking agents such as (S)-toliprolol and (S)-propanolol. (C) 2009 Elsevier Ltd. All rights reserved.