(±)-cis-2-bromocyclohexyl acetate | 5837-71-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: (±)-cis-2-bromocyclohexyl acetate
• 英文别名: acetic acid 2-bromocyclohexyl ester；(+/-)-cis-1-acetoxy-2-bromo-cyclohexane；(+/-)-cis-1-Acetoxy-2-brom-cyclohexan；[(1R,2S)-2-bromocyclohexyl] acetate
• CAS: 5837-71-8；35998-51-7；50421-18-6；61092-03-3；144788-93-2；145631-86-3
• 化学式: C₈H₁₃BrO₂
• 分子量: 221.094
• InChiKey: ZFEQKYDGSSHAGD-JGVFFNPUSA-N

物化性质

• 沸点：
  109-110 °C(Press: 11 Torr)
• 密度：
  1.3603 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

安全信息

• 海关编码：
  2915390090

反应信息

• 作为反应物：
  描述：

  (±)-cis-2-bromocyclohexyl acetate 在 甲醇 、 potassium carbonate 作用下， 以42%的产率得到(1R,2S)-2-bromocyclohexanol
  参考文献：
  名称：

  Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols

  摘要：

  The stereoisomers of cis-2-halocycloalkanols were resolved by a kinetically controlled transesterification with vinyl acetate in the presence of lipases in organic media. High enantioselectivities (ee >98%) and good isolated yields were obtained for all substrates using the appropriate lipase. Burkholderia cepacia lipase was the most efficient enzyme for the resolution of these substrates. The enantiomeric purities of the compounds were defined by derivatization with Mosher's acid and the absolute configurations were determined by chemical correlation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.011
• 作为产物：
  描述：

  2-溴环己酮 在 sodium tetrahydroborate 、 Burkholderia cepacia Amano PS lipase 作用下， 以 甲醇 、 甲基叔丁基醚 为溶剂， 反应 18.0h， 生成 (±)-cis-2-bromocyclohexyl acetate
  参考文献：
  名称：

  Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols

  摘要：

  The stereoisomers of cis-2-halocycloalkanols were resolved by a kinetically controlled transesterification with vinyl acetate in the presence of lipases in organic media. High enantioselectivities (ee >98%) and good isolated yields were obtained for all substrates using the appropriate lipase. Burkholderia cepacia lipase was the most efficient enzyme for the resolution of these substrates. The enantiomeric purities of the compounds were defined by derivatization with Mosher's acid and the absolute configurations were determined by chemical correlation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.011

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。
• Iodine(III)-Initiated Bromoacetoxylation of Olefins
  作者：Md. Abul Hashem、Alexander Jung、Monika Ries、Andreas Kirschning

  DOI：10.1055/s-1998-1596

  日期：1998.2

  A new and mild method for the bromoacetoxylation of olefins is presented, which is initiated by iodine(III). α-Acetoxy bromides 6-11 are generated from olefins 5 in the presence of tetraethylammonium bromide (1) and (diacetoxyiodo)benzene (2). The 1,2-addition to carbohydrate-derived enol ethers results in 2-deoxy-2-bromo-pyranosyl acetates which are versatile glycosyl donors for the synthesis of 2'-deoxy-2'-bromo glycosides 16.

  提出了一种新的温和方法，用于烯烃的溴乙酸酯化反应，该反应由碘(III)启动。在四乙基溴化铵(1)和(二乙酸氧碘)苯(2)的存在下，从烯烃5生成α-乙氧基溴化物6-11。对碳水化合物衍生的烯醇醚进行1,2-加成，得到2-脱氧-2-溴-吡喃糖乙酸酯，这些化合物是合成2'-脱氧-2'-溴糖苷16的多功能糖苷供体。
• 1,2-functionalization of cyclohexane using selenium intermediates
  作者：Angelo M. Morella、A.David Ward

  DOI：10.1016/s0040-4039(00)98866-x

  日期：1985.1

  The trans 1,2-phenylseleno acetate, acetamide, alcohol and nitrile of cyclohexane may be oxidized at selenium by halogens and the phenylseleno moiety displaced by halide to give high yields of 1,2 halide-containing products with cis geometry.

  环己烷的反式1,2-苯基硒代乙酸酯，乙酰胺，醇和腈可在硒中被卤素氧化，苯基硒代部分被卤化物取代，从而获得高收率的具有顺式几何构型的含1,2卤化物的产物。
• Reductions of .alpha.-substituted ketones by lithium diisopropylamide
  作者：Conrad Kowalski、Xavier Creary、Anthony J. Rollin、M. Carmel Burke

  DOI：10.1021/jo00407a011

  日期：1978.6