(1R,2R)-1-amino-1-phenyl-3-(phenylmethoxy)propan-2-ol | 250605-24-4

• 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: (1R,2R)-1-amino-1-phenyl-3-(phenylmethoxy)propan-2-ol
• 英文别名: (1R,2R)-1-amino-1-phenyl-3-phenylmethoxy-2-propanol；(1R,2R)-1-amino-1-phenyl-3-phenylmethoxypropan-2-ol
• CAS: 250605-24-4
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: WASGTYFFRPQWQA-JKSUJKDBSA-N

物化性质

• 沸点：
  428.2±45.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-(phenylmethoxy)propan-2-ol 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (4R,5R)-4-phenyl-5-(phenylmethoxymethyl)-1,3,2-oxazaborolidine
  参考文献：
  名称：

  A New Family of Modular Chiral Ligands for the Catalytic Enantioselective Reduction of Prochiral Ketones

  摘要：

  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.

  DOI：

  10.1021/jo990942q
• 作为产物：
  描述：

  (2S,3S)-O-benzyl-2,3-epoxy-3-phenylpropan-1-ol 在 sodium tetrahydroborate 、 sodium azide 、 lithium perchlorate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 40.0h， 生成 (1R,2R)-1-amino-1-phenyl-3-(phenylmethoxy)propan-2-ol
  参考文献：
  名称：

  A New Family of Modular Chiral Ligands for the Catalytic Enantioselective Reduction of Prochiral Ketones

  摘要：

  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.

  DOI：

  10.1021/jo990942q

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。
• 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。
• (<i>S</i>)-2-[(<i>R</i>)-Fluoro(phenyl)methyl]oxirane:  A General Reagent for Determining the ee of α-Chiral Amines
  作者：Sergi Rodríguez-Escrich、Dana Popa、Ciril Jimeno、Anton Vidal-Ferran、Miquel A. Pericàs

  DOI：10.1021/ol051110j

  日期：2005.9.1

  (S)-2-[(R)-Fluoro(phenyl)methyl]oxirane is a new, synthetic, yet enantiopure, chiral resolution reagent, readily obtained from enantiopure (2S,3S)-phenylglycidol, that reacts with a variety of alpha-chiral primary and secondary amines in a straightforward manner through a regioselective ring-opening. Diastereomeric products are easily identified and quantified by (19)F, (1)H, and (13)C NMR and by HPLC

  （S）-2-[（R）-氟（苯基）甲基]环氧乙烷是一种新的，合成的但对映体纯的手性拆分试剂，可轻松从对映纯（2S，3S）-苯基缩水甘油中获得，与多种α通过区域选择性开环以直接的方式-手性伯胺和仲胺。非对映异构产物易于通过（19）F，（1）H和（13）C NMR以及HPLC进行鉴定和定量，这使得该氟化化合物成为分析胺类规模混合物的最通用试剂。[反应：看文字]
• Chiral derivatives of semisquaric acid as new modular ligands for asymmetric catalysis
  作者：Sı́lvia Ferrer、Mireia Pastó、Belén Rodrı́guez、Antoni Riera、Miquel A. Pericàs

  DOI：10.1016/s0957-4166(03)00355-0

  日期：2003.6

  A family of enantiomerically pure ligands based on the cyclobutenedione structure, and containing either an enantiomerically pure amino alcohol or a diamine as the chiral element, has been synthesized. As first examples of their application, these versatile and modularly constructed ligands have been tested in the transfer hydrogenation of acetophenone and in the reduction using borane of this same substrate. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Parallel synthesis of modular chiral Schiff base ligands and evaluation in the titatium(IV) catalyzed asymmetric trimethylsilylcyanation of aldehydes
  作者：Belén Rodríguez、Mireia Pastó、Ciril Jimeno、Miquel A. Pericàs

  DOI：10.1016/j.tetasy.2005.11.022

  日期：2006.1

  Highly modular tridentate Schiff base ligands arising from enantiopure epoxyalcohols have been prepared and evaluated in catalysis using parallel methods. The key structural motifs and experimental parameters have been identified, allowing enantioselectivities of up to 77% ee in the titatium-catalyzed trimetbylsilyl cyanide addition to aldehydes. (c) 2005 Elsevier Ltd. All rights reserved.