(-)-(S)-2-bromo-3-phenylpropan-1-ol | 219500-45-5

• 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: (-)-(S)-2-bromo-3-phenylpropan-1-ol
• 英文别名: (S)-2-bromo-3-phenylpropanol；(S)-2-Bromo-3-phenylpropan-1-ol；(2S)-2-bromo-3-phenylpropan-1-ol
• CAS: 219500-45-5
• 化学式: C₉H₁₁BrO
• 分子量: 215.09
• InChiKey: HDBKHJLRENAESY-VIFPVBQESA-N

物化性质

• 沸点：
  288.8±20.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (-)-(S)-2-bromo-3-phenylpropan-1-ol 在 sodium hydroxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.75h， 生成 (S)-(+)-1-苯基-2-丙醇
  参考文献：
  名称：

  Chemo-enzymatic synthesis of the active enantiomer of the anorressant 2-benzylmorpholine

  摘要：

  Baker's yeast reduction of (Z)-alpha-bromocinnamaldehyde 1 in the presence of absorbing resins allows the easy preparation of the corresponding saturated bromo-alcohol 2 in high yields and enantiomeric excess. The absolute configuration is assigned through conversion into the (R)-phenyl oxirane 3 and 1-phenyl-2-propanol 4 of (S) absolute configuration. The (R)-epoxide is transformed into 6, the pharmacologically active enantiomer of the appetite suppressant 2-benzylmorpholine, to which the (R) configuration is assigned. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00432-7
• 作为产物：
  描述：

  (2Z)-2-bromo-3-phenyl-2-propenal 在 葡萄糖 、 fresh baker's yeast 、 XAD₁₁₈₀ resin 作用下， 以 水 为溶剂， 反应 48.0h， 以91%的产率得到(-)-(S)-2-bromo-3-phenylpropan-1-ol
  参考文献：
  名称：

  Chemo-enzymatic synthesis of the active enantiomer of the anorressant 2-benzylmorpholine

  摘要：

  Baker's yeast reduction of (Z)-alpha-bromocinnamaldehyde 1 in the presence of absorbing resins allows the easy preparation of the corresponding saturated bromo-alcohol 2 in high yields and enantiomeric excess. The absolute configuration is assigned through conversion into the (R)-phenyl oxirane 3 and 1-phenyl-2-propanol 4 of (S) absolute configuration. The (R)-epoxide is transformed into 6, the pharmacologically active enantiomer of the appetite suppressant 2-benzylmorpholine, to which the (R) configuration is assigned. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00432-7

文献信息

• Development of Ketone-Based Brominating Agents (KBA) for the Practical Asymmetric α-Bromination of Aldehydes Catalyzed by Tritylpyrrolidine
  作者：Aika Takeshima、Mio Shimogaki、Taichi Kano、Keiji Maruoka

  DOI：10.1021/acscatal.0c01596

  日期：2020.6.5

  Ketone-based brominating agents (KBA), ortho-substituted 2,2,2-tribromoacetophenones, have been developed, and the highly enantioselective and practical α-bromination of aldehydes with KBA was achieved. The reaction could be performed in the presence of only 0.1–1 mol % of catalyst without using a halogenated solvent at 0 °C and was found to be scalable.

  已经开发了基于酮的溴化剂（KBA），即邻位取代的2,2,2-三溴苯乙酮，并且实现了KBA对醛的高度对映选择性和实用性。该反应可以在仅0.1–1 mol％的催化剂存在下进行，而无需在0°C下使用卤化溶剂，并且发现该方法可扩展。
• Direct asymmetric bromination of aldehydes catalyzed by a binaphthyl-based secondary amine: highly enantio- and diastereoselective one-pot synthesis of bromohydrins
  作者：Taichi Kano、Fumitaka Shirozu、Keiji Maruoka

  DOI：10.1039/c0cc02739a

  日期：——

  One-pot stereoselective synthesis of bromohydrins as a useful chiral building block was achieved by the reaction of Grignard reagents with optically active alpha-bromoaldehydes, which were in situ generated by direct asymmetric bromination of aldehydes catalyzed by a binaphthyl-based secondary amine (S)-3.

  格氏试剂与旋光性α-溴醛的反应可实现一锅立体选择的溴代醇作为有用的手性结构单元，后者是通过基于双萘基仲胺（S）催化的醛直接不对称溴化而原位生成的-3。
• α-Amination of Aldehydes Catalyzed by In Situ Generated Hypoiodite
  作者：Jie-Sheng Tian、Kang Wai Jeffrey Ng、Jiun-Ru Wong、Teck-Peng Loh

  DOI：10.1002/anie.201204215

  日期：2012.9.3

  The metal‐free amination of different aldehydes is catalyzed by hypoiodite, which is generated by employing commercially available sodium percarbonate as the co‐oxidant. This approach has several advantages: it is a metal‐free oxidation that works under mild reaction conditions; furthermore, it has a wide substrate scope and does not give toxic by‐products from the co‐oxidant that is used.

  不含金属的胺化不同醛的由次碘酸根，这是通过采用商购获得的过碳酸钠作为共氧化剂生成的催化。这种方法有几个优点：它是一种不含金属的氧化即温和的反应条件下进行; 此外，它具有广泛的底物范围，并且不会从使用的助氧化剂中产生有毒副产物。
• Enantiospecific Solvolytic Functionalization of Bromochlorides
  作者：Alexander J. Burckle、Bálint Gál、Frederick J. Seidl、Vasil H. Vasilev、Noah Z. Burns

  DOI：10.1021/jacs.7b07792

  日期：2017.9.27

  Herein, we report that under mild solvolytic conditions, enantioenriched bromochlorides can be ionized, stereospecifically cyclized to an array of complex bromocyclic scaffolds, or intermolecularly trapped by exogenous nucleophiles. Mechanistic investigations support an ionic mechanism wherein the bromochloride serves as an enantioenriched bromonium surrogate. Several natural product-relevant motifs

  在本文中，我们报道了在温和的溶剂分解条件下，对映体富集的溴氯化物可以被电离，立体定向环化成一系列复杂的溴环骨架，或被外源性亲核试剂分子间捕获。机理研究支持离子机制，其中溴氯化物用作对映体富集的溴替代物。首次以高对映体控制形式以对映体富集的形式获得了几种与天然产物相关的基序，并将该技术应用于多环溴化天然产物的可扩展合成。包括烯烃，炔烃，杂环和环氧化物在内的亲核试剂阵列是溴诱导的环化反应中的有效陷阱，导致形成对映体富集的单环，双环和三环产物。该策略还适于肉桂酰溴氯化物与多种可商购的亲核试剂之间的分子间偶联。总的来说，这项工作表明，在各种官能团存在的情况下，溶剂化条件下富含对映体的氯化溴在构型上是稳定的。
• Organocatalytic Enantioselective α-Bromination of Aldehydes with <i>N</i>-Bromosuccinimide
  作者：George Hutchinson、Carla Alamillo-Ferrer、Martín Fernández-Pascual、Jordi Burés

  DOI：10.1021/acs.joc.2c00600

  日期：2022.6.17

  four examples reported to date require expensive, inconvenient brominating agents to achieve the desired products in excellent yields and enantioselectivities. The preferred brominating agent, N-bromosuccinimide (NBS), has been repeatedly discarded for these reactions because it results in low yields and relatively poor enantioselectivities. We describe a methodology that uses NBS and performs excellently

  尽管存在大量的有机催化、对映选择性转化，但醛的 α-溴化仍然是一个具有挑战性的反应。迄今为止报道的四个例子需要昂​​贵且不方便的溴化剂才能以优异的收率和对映选择性获得所需的产品。优选的溴化剂N-溴代琥珀酰亚胺 (NBS) 已在这些反应中反复丢弃，因为它导致低产率和相对较差的对映选择性。我们描述了一种使用 NBS 并在低催化剂负载、短反应时间和温和温度下表现出色的方法。