1-bromo-1-(2',4',6'-tri-tert-butylphenyl)ethene | 1618100-13-2

• 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-1-(2',4',6'-tri-tert-butylphenyl)ethene
• 英文别名: 1-bromo-1-(2,4,6-tri-tert-butylphenyl)ethene；2-(1-Bromoethenyl)-1,3,5-tritert-butylbenzene；2-(1-bromoethenyl)-1,3,5-tritert-butylbenzene
• CAS: 1618100-13-2
• 化学式: C₂₀H₃₁Br
• 分子量: 351.37
• InChiKey: MLPZTKDKJDAFNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (trimethylstannyl)lithium 、 1-bromo-1-(2',4',6'-tri-tert-butylphenyl)ethene 以 四氢呋喃 为溶剂， 以11%的产率得到[1-(2',4',6'-tri-tert-butylphenyl)vinyl](trimethyl)-stannane
  参考文献：
  名称：

  Highly syn selective addition of aqueous HBr to hydrophobically shielded arylalkynes

  摘要：

  Hydrophobically shielded alkynes HC C-aryl, carrying 2,6-di- and 2,4,6-tri-tert-butylphenyl as the aryl group, can add aqueous HBr on heating in moist chloroform solutions to produce pure H2C=C(-Br)-aryl (isolated yields 96%, no hydrolysis). Employment of DC C-aryl furnished initially only the E stereoisomer of DHC=C(-Br)-aryl (stereospecific syn addition), which was slowly both dedeuteriated and partially transformed to the Z stereoisomer by HBr. The strongly retarded HBr addition to H3C-C C-aryl in moist chloroform produced again more E than Z product, whereas a thermodynamic E/Z ratio of 10:87 was found in moist acetic acid. Substitution of Br by LiSnMe3 produced H2C=C(-SnMe3)-aryl with well resolved long range Sn-119 NMR coupling constants. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.002
• 作为产物：
  描述：

  1-溴-2,4,6-三叔丁基苯 在 吡啶 、 copper(l) iodide 、 正丁基锂 、 氯化亚砜 、 氢溴酸 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 甲基叔丁基醚 、 氯仿 、 正戊烷 为溶剂， 反应 5.75h， 生成 1-bromo-1-(2',4',6'-tri-tert-butylphenyl)ethene
  参考文献：
  名称：

  Highly syn selective addition of aqueous HBr to hydrophobically shielded arylalkynes

  摘要：

  Hydrophobically shielded alkynes HC C-aryl, carrying 2,6-di- and 2,4,6-tri-tert-butylphenyl as the aryl group, can add aqueous HBr on heating in moist chloroform solutions to produce pure H2C=C(-Br)-aryl (isolated yields 96%, no hydrolysis). Employment of DC C-aryl furnished initially only the E stereoisomer of DHC=C(-Br)-aryl (stereospecific syn addition), which was slowly both dedeuteriated and partially transformed to the Z stereoisomer by HBr. The strongly retarded HBr addition to H3C-C C-aryl in moist chloroform produced again more E than Z product, whereas a thermodynamic E/Z ratio of 10:87 was found in moist acetic acid. Substitution of Br by LiSnMe3 produced H2C=C(-SnMe3)-aryl with well resolved long range Sn-119 NMR coupling constants. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.002

文献信息

• Highly syn selective addition of aqueous HBr to hydrophobically shielded arylalkynes
  作者：Rudolf Knorr、Eva C. Rossmann、Monika Knittl、Petra Böhrer

  DOI：10.1016/j.tet.2014.05.002

  日期：2014.8

  Hydrophobically shielded alkynes HC C-aryl, carrying 2,6-di- and 2,4,6-tri-tert-butylphenyl as the aryl group, can add aqueous HBr on heating in moist chloroform solutions to produce pure H2C=C(-Br)-aryl (isolated yields 96%, no hydrolysis). Employment of DC C-aryl furnished initially only the E stereoisomer of DHC=C(-Br)-aryl (stereospecific syn addition), which was slowly both dedeuteriated and partially transformed to the Z stereoisomer by HBr. The strongly retarded HBr addition to H3C-C C-aryl in moist chloroform produced again more E than Z product, whereas a thermodynamic E/Z ratio of 10:87 was found in moist acetic acid. Substitution of Br by LiSnMe3 produced H2C=C(-SnMe3)-aryl with well resolved long range Sn-119 NMR coupling constants. (C) 2014 Elsevier Ltd. All rights reserved.