(2R)-1-azido-3-phenoxypropan-2-ol | 140630-37-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R)-1-azido-3-phenoxypropan-2-ol
• 英文别名: 1-azido-3-phenoxy-2-propanol；(R)-1-azido-3-phenoxy-2-propanol
• CAS: 140630-37-1
• 化学式: C₉H₁₁N₃O₂
• 分子量: 193.205
• InChiKey: ZWUXAZDVDTZWFW-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-1-azido-3-phenoxypropan-2-ol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (2R)-1-氨基-3-苯氧基-2-丙醇
  参考文献：
  名称：

  Enzyme assisted preparation of enantiomerically pure β-adrenergic blockers II. Building blocks of high optical purity and their synthetic conversion

  摘要：

  Based on previous screening results a series of potential building blocks 2-4 for beta-adrenergic blockers were prepared both by enzymatic hydrolysis and acyltransfer and further transformed into the corresponding oxiranes and aminoalcohols of defined absolute configurations.

  DOI：

  10.1016/s0957-4166(00)80191-3
• 作为产物：
  描述：

  (R)-α-(2-环氧乙基)苯甲醚 在 ammonium sulfate 、 sodium azide 作用下， 以 乙二醇甲醚 、 水 为溶剂， 反应 16.0h， 生成 (2R)-1-azido-3-phenoxypropan-2-ol 、 (2S)-2-azido-3-phenoxypropan-1-ol
  参考文献：
  名称：

  Aziridines as Precursors for Chiral Amide-Containing Surfactants

  摘要：

  Optically active aziridines can be used as precursors in the synthesis of several enantiopure amide-containing surfactants. Acylation of the aziridines is a convenient method for both the activation of the aziridine ring and the introduction of the hydrocarbon chain. The regioselectivity of the ring-opening reactions using dibenzyl phosphate could be controlled by varying the reaction temperature. In this way both regioisomers of the phospholipid analogues could be obtained. In the course of these experiments, an unprecedented rearrangement of a-acylamino phosphotriesters was observed. A mechanism for this group exchange reaction was proposed based on the compared reactivities of related compounds and FT-IR spectroscopic data Application of high pressures (12 kBar) for the ring opening of the activated aziridines with imidazole led to the efficient formation of the desired surfactant with complete regioselectivity.

  DOI：

  10.1021/jo962298a

文献信息

• Biocatalytic Cascade for the Synthesis of Enantiopure β-Azidoalcohols and β-Hydroxynitriles
  作者：Joerg H. Schrittwieser、Iván Lavandera、Birgit Seisser、Barbara Mautner、Wolfgang Kroutil

  DOI：10.1002/ejoc.200900091

  日期：2009.5

  one-pot reaction sequence starting from prochiral α-chloroketones leading to enantiopure β-azidoalcohols and β-hydroxynitriles is described. Asymmetric bioreduction of α-chloroketones by hydrogen transfer catalysed by an alcohol dehydrogenase (ADH) established the stereogenic centre in the first step to furnish enantiopure chlorohydrin intermediates. Subsequent biocatalysed ring closure to the epoxide

  描述了从前手性 α-氯酮开始导致对映纯 β-叠氮醇和 β-羟基腈的三步、两酶、一锅反应序列。通过由醇脱氢酶 (ADH) 催化的氢转移对 α-氯酮进行不对称生物还原，在第一步中建立了立体中心，以提供对映纯的氯醇中间体。随后通过非选择性卤代醇脱卤酶 (Hhe) 催化环氧化物的生物催化闭环和用叠氮化物 N3- 或氰化物 CN- 的亲核开环进行完全保留构型，得到对映体纯的 β-叠氮醇和 β-羟基腈，分别。合成了各种光学纯 β-叠氮醇和 β-羟基腈的两种对映异构体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Exploring the Biocatalytic Scope of a Novel Enantioselective Halohydrin Dehalogenase from an Alphaproteobacterium
  作者：Feng Xue、Xiangju Ya、Yuansong Xiu、Qi Tong、Yuqi Wang、Xinhai Zhu、He Huang

  DOI：10.1007/s10562-019-02659-0

  日期：2019.2

  AbstractA gene encoding halohydrin dehalogenase from an alphaproteobacterium (AbHHDH) was identified, cloned and over-expressed in Escherichia coli. AbHHDH was able to catalyze the stereoselective dehalogenation of prochiral and racemic halohydrins. It showed the highest enantioselectivity in the dehalogenation of 20 mM (R,S)-2-bromo-1-phenylethanol, which yielded (S)-2-bromo-1-phenylethanol with 99%

  摘要 鉴定、克隆并在大肠杆菌中过表达了编码来自α变形杆菌的卤代醇脱卤酶（AbHHDH）的基因。AbHHDH 能够催化前手性和外消旋卤代醇的立体选择性脱卤。它在 20 mM (R,S)-2-bromo-1-苯基乙醇的脱卤反应中表现出最高的对映选择性，生成 (S)-2-bromo-1-苯基乙醇，ee 为 99%，产率为 34.5%。此外，AbHHDH 以低至中等 (S)-对映选择性催化环氧化物的叠氮分解。当 (R,S)-苄基缩水甘油醚用作底物时，观察到最高的对映选择性 (E = 18.6)。由 HHDH 催化的连续动力学拆分用于合成手性 1-氯-3-苯氧基-2-丙醇。我们制备了对映纯 (S)-异构体，ee> 99% 的高对映纯度和 30 的产率。20 mM 底物的动力学分辨率为 7%（E 值：21.3）。从 40 到 150 mM (R,S)-1-chloro-3-phenoxy-2-propanol
• Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH
  作者：Ana Mikleušević、Ines Primožič、Tomica Hrenar、Branka Salopek-Sondi、Lixia Tang、Maja Majerić Elenkov

  DOI：10.1016/j.tetasy.2016.08.003

  日期：2016.10

  Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E = 1-16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-beta-azido alcohols and (R)-alpha-azido alcohols (ee >= 99%) were obtained. (C) 2016 Published by Elsevier Ltd.
• Enantioselective ring opening of epoxides with trimethylsilyl azide (TMSN3) in the presence of β-cyclodextrin: an efficient route to 1,2-azido alcohols
  作者：Ahmed Kamal、M Arifuddin、Maddamsetty V Rao

  DOI：10.1016/s0957-4166(99)00464-4

  日期：1999.11

  The ring opening of epoxides with nucleophiles such as TMSN3 and isopropylamine takes place enantioselectively in the presence of (beta-cyclodextrin under extremely mild conditions and the azido alcohols and amino alcohols are formed as (S)-isomers. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.