(±)-erythro-2-bromo-1-phenylpropyl acetate | 4962-46-3

• 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: (±)-erythro-2-bromo-1-phenylpropyl acetate
• 英文别名: acetic acid 2-bromo-1-phenylpropyl ester；(1RS,2SR)-1-acetoxy-2-bromo-1-phenyl-propane；(1RS,2SR)-1-Acetoxy-2-brom-1-phenyl-propan；erythro-1-Acetoxy-2-brom-1-phenyl-propan；[(1R,2S)-2-bromo-1-phenylpropyl] acetate
• CAS: 4962-46-3；21759-59-1；21759-60-4
• 化学式: C₁₁H₁₃BrO₂
• 分子量: 257.127
• InChiKey: BJRJQLJCJCYKFA-KWQFWETISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 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：

  (±)-erythro-2-bromo-1-phenylpropyl acetate 在 氢氧化钾 作用下， 生成 1-苯基-1,2-环氧丙烷
  参考文献：
  名称：

  Fischer, Chemische Berichte, 1957, vol. 90, p. 357,361

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 乙酸酐 作用下， 生成 (±)-erythro-2-bromo-1-phenylpropyl acetate
  参考文献：
  名称：

  Fischer, Chemische Berichte, 1957, vol. 90, p. 357,361

  摘要：

  DOI：

文献信息

• Comparative study of the vicinal functionalization of olefins with 2:1 bromide/bromate and iodide/iodate reagents
  作者：Manoj K. Agrawal、Subbarayappa Adimurthy、Bishwajit Ganguly、Pushpito K. Ghosh

  DOI：10.1016/j.tet.2009.01.095

  日期：2009.4

  halohydrins, halo methyl ethers, and halo acetates from olefins using 2:1 Br−/BrO3− and I−/IO3− reagents. In many cases both reagents afforded products selectively in high yields. The highest halogen atom efficiencies attained were 97% and 93% for Br−/BrO3− and I−/IO3−, respectively. Of the two reagents, I−/IO3− was established to be the preferred reagent for vicinal functionalization of linear alkenes and

  比较评价在邻位卤代醇，卤代甲基醚和卤代乙酸盐的合成由从使用2-烯烃：1溴- /的BrO 3 -和我- / IO 3 -试剂。在许多情况下，两种试剂都以高收率选择性地提供产物。得到最高卤素原子效率为97％和溴93％- /的BrO 3 -和我- / IO 3 - ，分别。这两个试剂，我- / IO 3 -已确定“丙烯酰胺”是用于直链烯烃的邻位官能化以及用于制备卤代乙酸酯的优选试剂。然而，只有溴- /的BrO 3 -是有效的邻位官能反式-二苯乙烯和查耳酮。
• A simple and facile method for regio- and stereoselective bromoformyloxylation and bromoacetoxylation of olefins using NH4Br and oxone®
  作者：Mameda Naresh、Peraka Swamy、Macharla Arun Kumar、Marri Mahender Reddy、Kodumuri Srujana、Nama Narender

  DOI：10.1016/j.tetlet.2014.04.103

  日期：2014.7

  temperature is described. This method is facile, environmentally friendly and cost effective. A variety of terminal, internal and cyclic alkenes reacted smoothly to give the corresponding bromoformate and acetate products in good to excellent yields. Moreover, 1,2-disubstituted olefins provided moderate to excellent diastereoselectivity.

  描述了在室温下不使用催化剂的情况下，在亲核源（DMF或DMA）中使用NH 4 Br和oxone®从烯烃制备溴甲酸酯和溴乙酸酯的温和有效方案。该方法简便，环保且具有成本效益。各种末端，内部和环状烯烃均能平稳反应，以高至极好的收率得到相应的溴甲酸酯和乙酸酯产物。而且，1,2-二取代的烯烃提供了中等至优异的非对映选择性。
• Polar additions to the styrene and 2-butene systems. I. Distribution stereochemistry of bromination products in acetic acid
  作者：John H. Rolston、Keith Yates

  DOI：10.1021/ja01034a033

  日期：1969.3
• Dimethylformamide, dimethylacetamide and tetramethylguanidine as nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes
  作者：Simon M. Ahmad、D. Christopher Braddock、Gemma Cansell、Stephen A. Hermitage

  DOI：10.1016/j.tetlet.2006.12.042

  日期：2007.2

  Dimethylformamide, dimethylacetamide and tetramethylguanidine were found to act as increasingly active catalysts for the bromolactonisation of gamma,delta- and delta,epsilon-unsaturated carboxylic acids with N-bromosuccinimide. The catalysts are readily removed in the work-up by washing with water to provide the pure bromolactone products without the need for column chromatography. Catalysis of the intermolecular bromoacetoxylation of alkenes with acetic acid and NBS by TMG was also demonstrated. (c) 2006 Elsevier Ltd. All rights reserved.
• MARPLES, B. A.;SAINT, C. G., SYNTH. COMMUN., 1982, 12, N 7, 545-555
  作者：MARPLES, B. A.、SAINT, C. G.

  DOI：——

  日期：——