(1R,2R)-1-amino-1-phenyl-3-(diphenylmethoxy)propan-2-ol | 250605-28-8

• 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: (1R,2R)-1-amino-1-phenyl-3-(diphenylmethoxy)propan-2-ol
• 英文别名: (1R,2R)-1-amino-1-phenyl-3-(benzhydryloxy)-2-propanol；(1R,2R)-1-amino-1-phenyl-3-diphenylmethoxy-2-propanol；(1R,2R)-1-amino-3-benzhydryloxy-1-phenylpropan-2-ol
• CAS: 250605-28-8
• 化学式: C₂₂H₂₃NO₂
• 分子量: 333.43
• InChiKey: AXCTXENGSODQPH-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 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：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-amino-1-phenyl-3-(diphenylmethoxy)propan-2-ol 在 硼烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 11.33h， 生成 (3S,4S)-1-[(1R,2R)-3-(benzhydryloxy)-2-hydroxy-1-phenylpropyl]-3-ethyl-4-(2-hydroxyethyl)piperidine
  参考文献：
  名称：

  动态动力学拆分和去对称化过程：哌啶的对映选择性合成的直接方法。

  摘要：

  报道了合成对映纯多取代哌啶的简单方法。它涉及直接产生已经在杂环上掺入碳取代基的手性非外消旋恶唑并[3，2-a]哌啶酮内酰胺，随后除去手性助剂。关键步骤是（R）-苯基甘醇或其他氨基醇与外消旋或手性δ-氧代（二）酸衍生物在高度立体选择性的过程中进行的环缩合反应，该过程涉及动态动力学拆分和/或非对映体或对映体酯基的去对称化。

  DOI：

  10.1002/chem.200600420
• 作为产物：
  描述：

  (2S,3S)-2-((diphenylmethoxy)methyl)-3-phenyloxirane 在 ammonium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 反应 23.0h， 以71%的产率得到(1R,2R)-1-amino-1-phenyl-3-(diphenylmethoxy)propan-2-ol
  参考文献：
  名称：

  Synthesis of enantiopure amino alcohols by ring-opening of epoxyalcohols and epoxyethers with ammonia

  摘要：

  Arylglycidols and their corresponding ethers undergo regioselective ring-opening with aqueous ammonia in the presence of organic co-solvents (isopropanol or 1,4-dioxane) to afford 1,2-amino alcohols in high yield. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.124

文献信息

• Phosphinooxazolines Derived from 3-Amino-1,2-diols: Highly Efficient ModularP-N Ligands
  作者：Dana Popa、Cristina Puigjaner、Montserrat Gómez、Jordi Benet-Buchholz、Anton Vidal-Ferran、Miquel A. Pericàs

  DOI：10.1002/adsc.200600599

  日期：2007.10.8

  palladium complexes have been used as chiral mediators in the asymmetric allylic alkylation reaction. The oxazoline moiety in 12 contains a C-4 aryl and a C-5 alkoxymethyl substituent that can be independently optimized for high catalytic activity and enantioselectivity. A methoxymethyl substituent at C-5 has been found to provide the best results in terms of enantioselectivity and activity in the alkylation

  制备了由对映体纯的β-氨基醇衍生而来的手性膦恶唑啉系列（12a–e），其钯配合物已用作不对称烯丙基烷基化反应中的手性介体。12中的恶唑啉部分含有一个C-4芳基和一个C-5烷氧基甲基取代基，可以针对高催化活性和对映选择性进行独立优化。在热和微波辅助活化下，已发现在C-5处的甲氧基甲基取代基在对映选择性和在多种烯丙基底物家族的烷基化中的活性方面提供了最佳结果。这项工作中描述的钯-膦基恶唑啉配合物非常坚固，因为不对称烯丙基烷基化反应中记录的对映选择性在20至130°C的温度范围内基本保持不变。在1，3-二苯基烯丙基和1，3-二甲基烯丙基烷基化底物之间观察到前所未有的对映选择性逆转，并且已经通过ONIOM QM / MM计算解释了这种行为的起因。
• Fine-Tuning of Modular Amino Alcohol Ligands for the Enantioselective Transfer Hydrogenation of Ketones
  作者：Mireia Pastó、Antoni Riera、Miquel A. Pericàs

  DOI：10.1002/1099-0690(200207)2002:14<2337::aid-ejoc2337>3.0.co;2-q

  日期：2002.7

  stereodefined, modular amino alcohols (3-alkoxy-1-amino-1-phenyl-2-propanols), in which the steric bulk of the alkoxy and amino substituents varies smoothly, has been synthesized from enantiomerically pure phenylglycidol, prepared by Sharpless epoxidation. These amino alcohols have been evaluated as ligands in the catalyzed [(amino alcohol)(arene)RuII] transfer hydrogenation of alkyl aryl ketones,

  一系列立体定义的模块化氨基醇（3-烷氧基-1-氨基-1-苯基-2-丙醇），其中烷氧基和氨基取代基的空间体积变化平稳，已从对映体纯苯基缩水甘油合成，制备如下无锐环氧化。这些氨基醇已被评估为催化 [(氨基醇)(芳烃)RuII] 烷基芳基酮转移氢化中的配体，2-丙醇作为氢源。氮取代基和烷氧基均已针对所考虑的过程中的最大对映选择性和催化活性进行了优化。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• Modular Bis(oxazoline) Ligands for Palladium Catalyzed Allylic Alkylation: Unprecedented Conformational Behaviour of a Bis(oxazoline) Palladium 3-1,3-Diphenylallyl Complex
  作者：Miquel Angel Pericàs、Cristina Puigjaner、Antoni Riera、Anton Vidal-Ferran、Montserrat Gómez、Francisco Jiménez、Guillermo Muller、Mercè Rocamora

  DOI：10.1002/1521-3765(20020916)8:18<4164::aid-chem4164>3.0.co;2-g

  日期：2002.9.16

  5-cis (6 c) stereochemistry at the individual rings have been prepared in high yield. Their eta(3)-allyl palladium complexes (8 a-g, 9 c and 10) have been used as catalytic precursors in allylic alkylation reactions with excellent enantioselectivities (up to 96 %) for the trans oxazoline derivatives, while Pd/6 c system was inactive. NMR studies on palladium eta(3)-1,3-diphenylallyl intermediates (11

  高产率地制备了在各个环上具有4,5-反式（5 ag）或4,5-顺式（6 c）立体化学的新对映体双（恶唑啉）家族。他们的eta（3）-烯丙基钯配合物（8 ag，9 c和10）已被用作烯丙基烷基化反应的催化前体，对恶唑啉衍生物具有出色的对映选择性（最高96％），而Pd / 6 c体系为不活跃。对钯eta（3）-1,3-二苯基烯丙基中间体（11a，c和e）的NMR研究表明，溶液中存在syn / syn-和syn / anti-烯丙基异构体。这类似于包含衍生自丙二酸的双（恶唑啉）的Pd烯丙基络合物中eta（3）-eta（1）-eta（3）异构的第一个例子。
• Highly enantioselective dynamic kinetic resolution and desymmetrization processes by cyclocondensation of chiral aminoalcohols with racemic or prochiral δ-oxoacid derivatives
  作者：Mercedes Amat、Oriol Bassas、Miquel A. Pericàs、Mireia Pastó、Joan Bosch

  DOI：10.1039/b413937b

  日期：——

  Cyclocondensation reactions of aminoalcohols and with racemic or prochiral delta-oxoacid derivatives provide polysubstituted lactams with high enantioselectivity in a process that involves dynamic kinetic resolution and/or desymmetrization of enantiotopic or diastereotopic ester groups.

  在涉及动态动力学拆分和/或对映异构或非对映异构酯基团的不对称化的过程中，氨基醇与外消旋或前手性δ-含氧酸衍生物的环缩合反应可提供具有高对映选择性的多取代内酰胺。
• A New Family of Modular Chiral Ligands for the Catalytic Enantioselective Reduction of Prochiral Ketones
  作者：Cristina Puigjaner、Anton Vidal-Ferran、Albert Moyano、Miquel A. Pericàs、Antoni Riera

  DOI：10.1021/jo990942q

  日期：1999.10.1

  A family of enantiomerically pure (4R,5R)-2-alkyl-4-phenyl-5-(R-oxymethyl) 1,3,2-oxazaborolidines (5) [boron substituent: H, CH3, n-C4H9; R-oxy group: CH3O, CH3OCH2CH2O, CH3(OCH2CH2)(2)O, PhCH2O, Ph2CHO, Ph3CO] has been prepared from (2S,3S)-2,3-epoxy-3-phenylpropanol (2) through a four-step sequence involving protection of the alcohol, regioselective ring-opening of the epoxide with sodium azide in acetonitrile in the presence of LiClO4, reduction of the azido group (H-2/PdC/MeOH or NaBH4/THF-MeOH), and formation of the oxazaborolidine ring with the appropriate boron reagent. Both the boron substituent and the R-oxy group have been optimized for maximal enantioselectivity in the reduction of prochiral ketones with borane. The optimal oxazaborolidine (5a-Me) [boron substituent: CH3; R-oxy group: CH3O] has been employed (10% molar amount, THF, 0 degrees C to room temperature) in the reduction of a representative family of 10 substrates comprising alkyl aryl ketones and dialkyl ketones. In these reductions, Ba-Rie induces the formation of secondary alcohols of S configuration with high enantioselectivity (93% mean enantiomeric excess). The origin of the enantioselectivity in the reduction has been rationalized by means of semiempirical AM1 calculations.