(R)-(-)-s-butyl bromide | 5787-33-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: (R)-(-)-s-butyl bromide
• 英文别名: (R)-(-)-2-bromobutane；(R)-(-)-butyl bromide；(R)-sec-butyl bromide；(R)-2-bromobutane；(R)-2-bromo-butane；(R)-sec-butyl bromide；Butane, 2-bromo-, (2R)-；(2R)-2-bromobutane
• CAS: 5787-33-7
• 化学式: C₄H₉Br
• 分子量: 137.019
• InChiKey: UPSXAPQYNGXVBF-SCSAIBSYSA-N

物化性质

• 沸点：
  90.7±8.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (R)-(-)-s-butyl bromide 在 溴 作用下， 生成 (+)-(3R)-2,2,3-Tribrombutan
  参考文献：
  名称：

  Photobromination of (-)-(2R)-2-bromobutane with bromine-81

  摘要：

  DOI：

  10.1021/ja00450a052
• 作为产物：
  描述：

  (S)-(+)-2-丁醇 在 三溴化磷 作用下， 以79.1%的产率得到(R)-(-)-s-butyl bromide
  参考文献：
  名称：

  Asymmetric alkylation of .beta.-keto esters with optically active sulfonium salts

  摘要：

  DOI：

  10.1021/jo00271a025

文献信息

• Enantioselectivity of Haloalkane Dehalogenases and its Modulation by Surface Loop Engineering
  作者：Zbynek Prokop、Yukari Sato、Jan Brezovsky、Tomas Mozga、Radka Chaloupkova、Tana Koudelakova、Petr Jerabek、Veronika Stepankova、Ryo Natsume、Jan G. E. van Leeuwen、Dick B. Janssen、Jan Florian、Yuji Nagata、Toshiya Senda、Jiri Damborsky

  DOI：10.1002/anie.201001753

  日期：2010.8.16

  In the loop: Engineering of the surface loop in haloalkane dehalogenases affects their enantiodiscrimination behavior. The temperature dependence of the enantioselectivity (lnE versus 1/T) of β‐bromoalkanes by haloalkane dehalogenases is reversed (red data points) by deletion of the surface loop; the selectivity switches back when an additional single‐point mutation is made. This behavior is not observed

  在回路中：卤代烷脱卤酶表面回路的工程设计会影响其对映异构行为。卤代烷脱卤酶对β-溴代烷烃的对映选择性（ln E对1 / T）的温度依赖性通过消除表面环而被逆转（红色数据点）。当进行其他单点突变时，选择性会切换回去。对于α-溴代酸酯未观察到此行为。
• Alkylation of Several Nucleophiles with Alkylsulfonium Salts
  作者：Kazuyuki Umemura、Haruo Matsuyama、Nobumasa Kamigata

  DOI：10.1246/bcsj.63.2593

  日期：1990.9

  group was reacted with a phenolate ion, an optically active (R)-s-butyl phenyl ether was obtained with an inversion of the configuration at the chiral carbon atom. A reaction mechanism via a sulfurane intermediate is proposed for the alkylation of the phenolate ion with alkylsulfonium salts. The relative reactivities for the alkylation of several nucleophiles with dialkylphenylselenonium salts (12) were

  已经研究了二烷基苯基锍盐 (1) 与几种亲核试剂如酚、胺、烯醇盐离子和硫醇盐离子的反应。锍盐的烷基对酚盐离子（硬亲核试剂）的相对反应性如下：我:Et:i-Pr =1.0:1.34:3.44。在对甲苯硫醇盐离子（软亲核试剂）与 1 的烷基化中，发现了相反的反应性（Me:Et:i-Pr=1.0:0.22:0.03）。当具有旋光性 (S)-仲丁基的锍盐 (1e) 与酚盐离子反应时，获得旋光性 (R)-仲丁基苯基醚，其手性碳的构型发生反转原子。提出了通过硫烷中间体的反应机制，用于苯酚离子与烷基锍盐的烷基化。
• Studies on the Stereochemistry in the Alkylation of Enolate Ion of Cyclic β-Keto Ester with Sulfonium Salts Containing Optically Active Alkyl Groups
  作者：Michio Kobayashi、Kazuyuki Umemura、Haruo Matsuyama

  DOI：10.1246/cl.1987.327

  日期：1987.2.5

  of cyclic β-keto ester with racemic sulfonium salts containing optically active alkyl groups such as (S)-2-octyl and (S)-2-butyl was found to afford C-alkylated products with inversion of configuration at asymmetric alkyl carbon atom. Stereochemical reaction course via formation of S–O sulfurane intermediate and successive stereoselective intramolecular alkyl migration to enolate is described.

  发现环状 β-酮酯与含有旋光烷基（如 (S)-2-辛基和 (S)-2-丁基）的外消旋锍盐的烷基化得到 C-烷基化产物，在不对称烷基碳原子处发生构型反转. 描述了通过形成 S-O 硫烷中间体和连续立体选择性分子内烷基迁移到烯醇的立体化学反应过程。
• Synthesis and Mesomorphic Characterisation of Chiral Homologues
  作者：Jayrang S. Dave、Meera R. Menon、Pratik R. Patel

  DOI：10.1080/10587250108025027

  日期：2001.8

  Chiral liquid crystals have attracted considerable interest as they exhibit a good variety of modulated phases. We have synthesised a homologous series viz., 4-(4'-n-alkoxy benzoyloxy) benzylidene-4 " -1-(s)-methyl propoxy anilines, incorporating a terminal chiral centre, inorder to obtain better understanding of the relationship between molecular structure and appearance of SmC* phase in the molecules. It is observed that, in the present series the lower members upto butyl are pure nematogens, while pentyl to hexadecyl derivatives exhibit classical smectic as well as nematic mesophases. An additional smectic C* phase is observed in the middle octyl to dodecyl homologues. The homologues have been characterised by IR, NMR and DSC. Their mesomorphic properties have been compared with structurally related homologous series.
• Molecular Rearrangements Involving Optically Active Radicals. V. The Rearrangement of Optically Active Alkyl Phenyl Ethers¹
  作者：Murray M. Sprung、Everett S. Wallis

  DOI：10.1021/ja01323a020

  日期：1934.8