(3R,4S)-4-(3-bromophenyl)-3,4-dihydroxybutan-2-one | 956403-64-8

• 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: (3R,4S)-4-(3-bromophenyl)-3,4-dihydroxybutan-2-one
• 英文别名: (3R,4S)-3,4-dihydroxy-4-(3-bromphenyl)butan-2-one
• CAS: 956403-64-8
• 化学式: C₁₀H₁₁BrO₃
• 分子量: 259.1
• InChiKey: FFEMKKFKGKPXPI-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  间溴苯甲醛 、 羟基丙酮 在 (1S,2S)-N'-methyl-N'-((S)-1-phenylethyl)cyclohexane-1,2-diamine 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以79%的产率得到(3R,4S)-4-(3-bromophenyl)-3,4-dihydroxybutan-2-one
  参考文献：
  名称：

  在水介质中高度对映选择性的有机催化合成和反羟醛反应

  摘要：

  Abstractmagnified imageWe have synthesized chiral diamines that efficiently catalyze the syn‐ and anti‐aldol reactions in aqueous medium with high diastereo‐ and enantioselectivities. The product, thus obtained, was further reduced selectively to give syn‐configured 1,2,3‐triol, an important subunit present in various monosaccharides and natural products such as (+)‐boronolide.

  DOI：

  10.1002/adsc.200900122

文献信息

• Pepsin-catalyzed direct asymmetric aldol reactions for the synthesis of vicinal diol compounds
  作者：Ling-Yu Li、Da-Cheng Yang、Zhi Guan、Yan-Hong He

  DOI：10.1016/j.tet.2015.01.061

  日期：2015.3

  The catalytic promiscuity of pepsin from porcine gastric mucous was observed in catalysis of the direct asymmetric aldol reactions of aromatic aldehydes with acetones, which were substituted by hydroxy-, dihydroxy-, methoxy- and benzyloxy- for the synthesis of diol compounds in acetonitrile. This biocatalysis was also applicable to the aldol reactions of cyclic or hetereocyclic ketones with aromatic

  在催化芳香族醛与丙酮直接不对称醛醇缩合反应的催化过程中，观察到了胃蛋白酶对胃蛋白酶的混杂作用，丙酮醛被羟基，二羟基，甲氧基和苄氧基所取代，从而在乙腈中合成二醇化合物。该生物催化也适用于环状或杂环酮与芳族醛的醛醇缩合反应。获得了高达87％的产率，高达> 99/1 dr的非对映选择性和高达75％ee的对映选择性。
• Insights into Substituent Effects of Benzaldehyde Derivatives in a Heterogeneous Organocatalyzed Aldol Reaction
  作者：Graziano Di Carmine、Fabio Pesciaioli、Simeng Wang、Arianna Sinibaldi、Giuliana Giorgianni、Christopher M. A. Parlett、Armando Carlone、Carmine D'Agostino

  DOI：10.1002/cctc.202200405

  日期：2022.7.21

  heterogenous organocatalysis is undoubtedly critical to develop new and higher performing catalysts. NMR relaxation techniques provide very useful insights into adsorption effects of the aldehyde partner in an organocatalyzed aldol reaction.

  吸附：了解影响和控制多相有机催化的因素对于开发新的和更高性能的催化剂无疑是至关重要的。核磁共振弛豫技术提供了非常有用的见解，了解醛伴侣在有机催化醛醇反应中的吸附效果。
• Simple and inexpensive threonine-based organocatalysts for the highly diastereo- and enantioselective direct large-scale syn-aldol and anti-Mannich reactions of α-hydroxyacetone
  作者：Chuanlong Wu、Xiangkai Fu、Shi Li

  DOI：10.1016/j.tetasy.2011.06.022

  日期：2011.5

  Simple and inexpensive threonine-based organocatalysts that promote syn-aldol reactions and three-component asymmetric anti-Mannich reactions of alpha-hydroxyacetone achieving a respectable level of enantioselectivities are reported. The syn-aldol products could be obtained with up to a 99:1 syn/anti ratio and > 99% ee while the anti-Mannich products could be obtained with up to a 96:4 anti/syn ratio and > 99% ee. Catalyst 1c can be used efficiently on a large-scale with the enantioselectivities of the syn-aldol and anti-Mannich reactions being maintained at the same level, which offers a great possibility for application in industry. (C) 2011 Elsevier Ltd. All rights reserved.
• Highly Enantioselective Organocatalytic<i>syn</i>- and<i>anti</i>-Aldol Reactions in Aqueous Medium
  作者：Monika Raj、Gopal S. Parashari、Vinod K. Singh

  DOI：10.1002/adsc.200900122

  日期：2009.6

  Abstractmagnified imageWe have synthesized chiral diamines that efficiently catalyze the syn‐ and anti‐aldol reactions in aqueous medium with high diastereo‐ and enantioselectivities. The product, thus obtained, was further reduced selectively to give syn‐configured 1,2,3‐triol, an important subunit present in various monosaccharides and natural products such as (+)‐boronolide.