rac-(2S,3R)-ethyl 2,3-dibromo-3-phenylpropanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: rac-(2S,3R)-ethyl 2,3-dibromo-3-phenylpropanoate
• 英文别名: (trans)-ethyl 2,3-dibromo-3-phenylpropanoate；ethyl (2R,3S)-2,3-dibromo-3-phenylpropanoate
• 化学式: C₁₁H₁₂Br₂O₂
• 分子量: 336.023
• InChiKey: CCYOCUPSKJUNMD-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  rac-(2S,3R)-ethyl 2,3-dibromo-3-phenylpropanoate 在 N-甲基哌啶 作用下， 以 苯 为溶剂， 以99%的产率得到ethyl 2-bromo-3-phenylacrylate
  参考文献：
  名称：

  Stereoselective synthesis of a novel 2-aza-7-oxabicyclo[3.3.0]octane as neurokinin-1 receptor antagonist

  摘要：

  A novel neurokinin-1 receptor antagonist, (+/-)-(IR*,3S*,4S*,5S*)-4-[(N-(2-methoxy-5-trifluoromethoxybenzyl)amino]-3-phenyl-2-aza-7-oxabicyclo[3.3.0]octane (1), was synthesized stereo selectively using Padwa's intramolecular 1,3-dipolar cycloaddition methodology as the key step. Compound (+/-)-1 showed high affinity for the NK-1 receptors in human IM-9 cells with an IC(50) value of 0.22 nM. This new structural scaffold demonstrated significant in vivo antagonistic activity in the guinea pig ureter capsaicin-induced plasma extravasation model with an ED(50) value of 1 -10 mg/kg, po. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.010
• 作为产物：
  描述：

  肉桂酸乙酯 在 草酰溴 、 三苯基氧化膦 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 36.0h， 以88%的产率得到rac-(2S,3R)-ethyl 2,3-dibromo-3-phenylpropanoate
  参考文献：
  名称：

  三苯膦氧化物催化的不饱和化合物的立体选择性多溴化和二溴化。

  摘要：

  已经开发出新颖的PPh 3 O催化的溴phosph盐介导的α，β-不饱和酯和β，γ-不饱和α-酮酸酯的二溴化。获得的产物具有良好至优异的产率和优异的非对映选择性。该二溴化反应是对二溴化领域的良好补充。

  DOI：

  10.1039/c4cc02847c

文献信息

• Reduction with Samarium(0). Debromination of<i>vic</i>-Dibromides to Alkenes
  作者：Reiko Yanada、Kiyoshi Bessho、Kazuo Yanada

  DOI：10.1246/cl.1994.1279

  日期：1994.7

  Three electrons from Sm(0) to Sm(III) can be available during the title reduction which was achieved in 90–95% yield with vic-dibromides such as trans-10,11-dibromodibenzosuberone, meso- and dl-1,2-dibromo-1,2-diphenylethane, ethyl 2,3-dibromo-3-phenylpropionate, 2,3-dibromo-3-phenylpropionic acid, and cholesterol dibromide. These reductions were accelerated with a catalytic amount of acid.

  在标题还原过程中，Sm(0)向Sm(III)转移三个电子的操作可以通过使用诸如反式-10,11-二溴二苯并苏勃酮、内消旋和外消旋-1,2-二溴-1,2-二苯基乙烷、乙基2,3-二溴-3-苯基丙酸酯、2,3-二溴-3-苯基丙酸以及胆固醇二溴化物等邻二溴化物来实现，产率高达90-95%。这些还原过程可通过加入少量酸催化加速。
• Water Accelerated Sm/TMSCl Reductive System: Debromination of<i>VIC</i>—Dibromides and Reduction of Sodium Alkyl Thiosulfates
  作者：Xiaoliang Xu、Ping Lu、Yongmin Zhang

  DOI：10.1080/00397910008087241

  日期：2000.6

  Abstract A simple and efficient method for the debromination of vic-dibromides to (E)-alkenes and reduction of sodium alkyl thiosulfates to disulfides promoted by Sm/TMSCl/H2O (trace) has been described.

  摘要 描述了一种在 Sm/TMSCl/H2O（痕量）促进下将 vic-二溴化物脱溴为 (E)-烯烃和将烷基硫代硫酸钠还原为二硫化物的简单有效方法。
• Direct sustainable bromination of alkenes in aqueous media and basic ionic liquids
  作者：Patrizia Primerano、Massimiliano Cordaro、Angela Scala

  DOI：10.1016/j.tetlet.2013.05.097

  日期：2013.7

  Electron-rich and electron-poor alkenes have been dibrominated using a rapid and sustainable procedure. The reactions were conducted in aqueous medium and basic ionic liquids which catalyzed the direct addition of bromine. The protocol leads to remarkable results, high yields under mild conditions, complete chemo- and stereo-selectivity and allows the recycling of ionic liquids, reducing costs, and

  富电子和贫电子的烯烃已使用一种快速且可持续的方法进行了二溴化处理。反应在水性介质和碱性离子液体中进行，所述碱性离子液体催化溴的直接添加。该方案可产生显着的结果，在温和条件下具有高收率，完全的化学和立体选择性，并允许离子液体的再循环，降低成本和对环境的影响。
• Visible-Light Photoredox Catalysis: Dehalogenation of Vicinal Dibromo-, α-Halo-, and α,α-Dibromocarbonyl Compounds
  作者：Tapan Maji、Ananta Karmakar、Oliver Reiser

  DOI：10.1021/jo102239x

  日期：2011.1.21

  vic-Dibromo-, α-halo-, or α,α-dibromocarbonyl compounds can be efficiently dehalogenated using catalytic tris(2,2′-bipyridyl)ruthenium dichloride (Ru(bpy)3Cl2) in combination with 1,5-dimethoxynaphthalene (DMN) and ascorbate as sacrificial electron donor. For this process, a visible light promoted photocatalytic cycle is proposed that involves the reduction of carbon halogen bonds via free radical

  使用催化三氯化三（2,2'-联吡啶基）钌（Ru（bpy）3 Cl 2）与1,5-结合可以有效地使vic -Dibromo-，α-卤代或α，α-二溴代羰基化合物脱卤二甲氧基萘（DMN）和抗坏血酸盐作为牺牲电子给体。对于该方法，提出了可见光促进的光催化循环，该循环涉及通过自由基中间体还原碳卤键。
• PPh₃O as an Activating Reagent for One-Pot Stereoselective Syntheses of Di- and Polybrominated Esters from Simple Aldehydes
  作者：Tian-Yang Yu、Hao Wei、Yong-Chun Luo、Yao Wang、Zhu-Yin Wang、Peng-Fei Xu

  DOI：10.1021/acs.joc.5b02618

  日期：2016.4.1

  An efficient one-pot method for the syntheses of di- and polybrominated esters from readily available aldehydes is reported. The direct use of the in situ generated byproduct PPh3O in the following reactions greatly improves the efficiency of the cascade. Also, the substrate scope of the reaction is proved to be broad.

  报道了一种由一应俱全的醛合成二溴和多溴代酯的有效的一锅法。在以下反应中直接使用原位生成的副产物PPh 3 O大大提高了级联反应的效率。而且，反应的底物范围被证明是广泛的。