1-bromo-3-(but-2-en-2-yl)benzene | 408307-64-2

• 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: 1-bromo-3-(but-2-en-2-yl)benzene
• 英文别名: 1-Bromo-3-but-2-en-2-ylbenzene
• CAS: 408307-64-2
• 化学式: C₁₀H₁₁Br
• 分子量: 211.101
• InChiKey: SVPXATOHIOEZAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  1-bromo-3-(but-2-en-2-yl)benzene 在 platinum(IV) oxide 、 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.5h， 生成 (3-(sec-butyl)phenyl)boronic acid
  参考文献：
  名称：

  基于Teraryl的α-螺旋模拟物的模块合成，第1部分：具有两个电子区分的离去基团的核心片段的合成

  摘要：

  基于Teraryl的α-螺旋模拟物已被证明是抑制蛋白质-蛋白质相互作用（PPI）的有用化合物。我们开发了一种模块化且灵活的方法来合成基于芳基的α-螺旋模拟物。我们策略的核心是使用苯核心单元，该核心单元在用于三联苯组装的Pd催化交叉偶联中具有两个不同反应性的离去基团。通过卤素/重氮途径和卤素/三氟甲磺酸途径，已经成功建立了两种策略。报道了具有脂肪族（Ala，Val，Leu，Ile），芳香族（Phe），极性（Cys，Lys），亲水性（Ser，Gln）和酸性（Glu）氨基酸侧链的核心结构单元的合成。

  DOI：

  10.1002/chem.201203005
• 作为产物：
  描述：

  乙基三苯基溴化膦 、 3'-溴苯乙酮 在 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 反应 15.5h， 生成 1-bromo-3-(but-2-en-2-yl)benzene
  参考文献：
  名称：

  Highly Enantioselective and Anti-Diastereoselective Catalytic Intermolecular Glyoxylate–Ene Reactions: Effect of the Geometrical Isomers of Alkenes

  摘要：

  An efficient method for the synthesis of homoallylic alcohols with high enantioselectivities and anti-diastereoselectivities via an In(III)-catalyzed intermolecular glyoxylateene reaction has been developed. The geometrical isomers of alkenes were shown to have different reactivities. Only the isomers of the alkenes having a proton beta-cis to the substituent reacted in this catalytic system.

  DOI：

  10.1021/acs.orglett.5b01151

文献信息

• Access to “Friedel–Crafts-Restricted” <i>tert</i>-Alkyl Aromatics by Activation/Methylation of Tertiary Benzylic Alcohols
  作者：Joshua A. Hartsel、Derek T. Craft、Qiao-Hong Chen、Ming Ma、Paul R. Carlier

  DOI：10.1021/jo202371c

  日期：2012.4.6

  Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl2 or concentrated HCl and then treated with trimethylaluminum, affording the desired products in 68-97% yields (22 examples). This reaction sequence is successful in the presence of a variety of functional groups, including acid-sensitive and Lewis-basic groups. In addition to t-Bu groups, 1,1-dimethylpropyl and 1-ethyl-1-methylpropyl groups can also be installed using this method.
• The Preparation and Polymerization of Some Alkyl Styrenes^1,2
  作者：C. S. Marvel、R. E. Allen、C. G. Overberger

  DOI：10.1021/ja01210a051

  日期：1946.6
• Stereoconvergent Approach to the Enantioselective Construction of α‐Quaternary Alcohols by Radical Epoxide Allylation
  作者：Sebastian Höthker、Annika Plato、Stefan Grimme、Zheng-Wang Qu、Andreas Gansäuer

  DOI：10.1002/anie.202405911

  日期：——

  Abstract: We describe a highly stereoconvergent radical epoxide allylation towards diastereomerically and enantiomerically enriched α‐quaternary alcohols in two steps from olefins. Our approach combines the stereospecifity and enantioselectivity of the Shi epoxidation with the unprecedented Ti(III)‐promoted intramolecular radical group transfer allylation of epoxides. A directional isomerization step via configurationally labile radical intermediates enables the selective preparation of all carbon quaternary stereocenters in a unique fashion.
• Highly Enantioselective and <i>Anti</i>-Diastereoselective Catalytic Intermolecular Glyoxylate–Ene Reactions: Effect of the Geometrical Isomers of Alkenes
  作者：Xiang Zhang、Min Wang、Ran Ding、Yun-He Xu、Teck-Peng Loh

  DOI：10.1021/acs.orglett.5b01151

  日期：2015.6.5

  An efficient method for the synthesis of homoallylic alcohols with high enantioselectivities and anti-diastereoselectivities via an In(III)-catalyzed intermolecular glyoxylateene reaction has been developed. The geometrical isomers of alkenes were shown to have different reactivities. Only the isomers of the alkenes having a proton beta-cis to the substituent reacted in this catalytic system.
• A Modular Synthesis of Teraryl-Based α-Helix Mimetics, Part 1: Synthesis of Core Fragments with Two Electronically Differentiated Leaving Groups
  作者：Martin Peters、Melanie Trobe、Hao Tan、Rolf Kleineweischede、Rolf Breinbauer

  DOI：10.1002/chem.201203005

  日期：2013.2.11

  developed a modular and flexible approach for the synthesis of teraryl‐based α‐helix mimetics. Central to our strategy is the use of a benzene core unit featuring two leaving groups of differentiated reactivity in the Pd‐catalyzed cross‐coupling used for terphenyl assembly. With the halogen/diazonium route and the halogen/triflate route, two strategies have successfully been established. The synthesis of core

  基于Teraryl的α-螺旋模拟物已被证明是抑制蛋白质-蛋白质相互作用（PPI）的有用化合物。我们开发了一种模块化且灵活的方法来合成基于芳基的α-螺旋模拟物。我们策略的核心是使用苯核心单元，该核心单元在用于三联苯组装的Pd催化交叉偶联中具有两个不同反应性的离去基团。通过卤素/重氮途径和卤素/三氟甲磺酸途径，已经成功建立了两种策略。报道了具有脂肪族（Ala，Val，Leu，Ile），芳香族（Phe），极性（Cys，Lys），亲水性（Ser，Gln）和酸性（Glu）氨基酸侧链的核心结构单元的合成。