(3R,4S)-3,4-dihydroxy-4-(2-bromophenyl)butan-2-one | 956403-69-3

• 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)-3,4-dihydroxy-4-(2-bromophenyl)butan-2-one
• 英文别名: (3R,4S)-4-(2-bromophenyl)-3,4-dihydroxybutan-2-one
• CAS: 956403-69-3
• 化学式: C₁₀H₁₁BrO₃
• 分子量: 259.1
• InChiKey: QUKMNAUHZXOBLZ-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：

  邻溴苯甲醛 、 羟基丙酮 在 CHF₃O₃S*C₁₃H₂₀N₂ 作用下， 以 N-甲基吡咯烷酮 、 正己烷 为溶剂， 反应 24.0h， 生成 (3R,4S)-3,4-dihydroxy-4-(2-bromophenyl)butan-2-one 、 4-(2-bromophenyl)-3,4-dihydroxybutan-2-one
  参考文献：
  名称：

  天然氨基酸衍生的手性伯叔叔二胺催化剂用于羟基酮的顺式-羟醛反应

  摘要：

  从伯天然氨基酸设计合成了一系列伯叔二胺催化剂。这些新的手性催化剂在α-羟基酮的直接醛醇缩合反应中的应用显示出非常好的催化活性（高达97％的收率）和高的合成选择性（高达syn / anti = 30：1，99％ee）。

  DOI：

  10.1021/jo802557p

文献信息

• Towards Sustainable Amino Acid Derived Organocatalysts for Asymmetric <i>syn</i> -Aldol Reactions
  作者：Vasiliy V. Gerasimchuk、Alexandr S. Kucherenko、Artem N. Fakhrutdinov、Michael G. Medvedev、Yulia V. Nelyubina、Sergei G. Zlotin

  DOI：10.1002/ejoc.201700166

  日期：2017.5.3

  side-processes responsible for the fast deactivation of primary amino acid derived organocatalysts in asymmetric aldol reactions are identified. A new ionic-liquid-supported (S)-valine-/(S)-α,α-diphenylserinol-derived catalyst (9) is designed on the basis of these results and exhibits much better recyclability in asymmetric syn-aldol reactions between hydroxyacetone and aldehydes. Furthermore, this catalyst

  鉴定了在不对称醛醇反应中导致伯氨基酸衍生的有机催化剂快速失活的不良副过程。基于这些结果设计了一种新的离子液体负载的 (S)-缬氨酸-/(S)-α,α-二苯基丝氨醇衍生催化剂 (9) 并在羟基丙酮之间的不对称合成羟醛反应中表现出更好的可回收性和醛类。此外，该催化剂似乎可用于通过不对称合成羟醛/内酯化级联反应立体选择性合成天然存在的 1(3H)-isobenzofuran-1-one 支架。
• Highly Efficient Organocatalyzed Direct Asymmetric Aldol Reactions of Hydroxyacetone and Aldehydes
  作者：Xiaoyu Wu、Zhixiong Ma、Zhengqing Ye、Shan Qian、Gang Zhao

  DOI：10.1002/adsc.200800558

  日期：2009.1

  Novel organocatalysts derived from L-threonine and L-leucine have been synthesized for catalyzing direct aldol reactions of hydroxycetone and unactivated aliphatic aldehydes with as low as 2 mol% loading of the catalyst, good to excellent yields and excellent enantioselectivities have been achieved for aliphatic aldehydes, whereas aromatic aldehydes yield only moderate enantioselectivities.

  合成了衍生自L-苏氨酸和L-亮氨酸的新型有机催化剂，用于催化羟基丙酮与未活化的脂族醛的直接醛醇缩合反应，催化剂的负载量低至2 mol％，对脂族醛具有良好至优异的收率和优异的对映选择性。 ，而芳族醛仅产生中等对映选择性。
• Highly Enantioselective Direct <i>syn</i>- and <i>anti</i>-Aldol Reactions of Dihydroxyacetones Catalyzed by Chiral Primary Amine Catalysts
  作者：Sanzhong Luo、Hui Xu、Long Zhang、Jiuyuan Li、Jin-Pei Cheng

  DOI：10.1021/ol703023t

  日期：2008.2.1

  We present herein simple primary-tertiary diamine-Bronsted acid conjugates that catalyze both syn- and anti-adol reactions of dihydroxyacetones (DHAs) with high diastereoselectivities and enantioselectivities. This type of organocatalysts functionally mimics all four DHA aldolases, namely L-fuculose-1-phosphate aldolase, D-tagatose-1,6-diphosphate aldolase, D-fructose-1,6-diphosphate aldolase, and L-rhamnulose-1-phosphate aldolase.
• 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.