3-(5-bromo-2-methylenepentyl)benzo[b]thiophene | 1419175-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-(5-bromo-2-methylenepentyl)benzo[b]thiophene
• 英文别名: 3-(5-Bromo-2-methylidenepentyl)-1-benzothiophene；3-(5-bromo-2-methylidenepentyl)-1-benzothiophene
• CAS: 1419175-04-4
• 化学式: C₁₄H₁₅BrS
• 分子量: 295.243
• InChiKey: HTEWHGRIZSGCGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-甲醛苯并噻吩 在 sodium tetrahydroborate 、 氯化亚砜 、 trans-bis(dicyclohexylphenylphosphine)nickel (o-tolyl) chloride 、 三乙基硅基三氟甲磺酸酯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.63h， 生成 、 3-(5-bromo-2-methylenepentyl)benzo[b]thiophene
  参考文献：
  名称：

  Simplifying Nickel(0) Catalysis: An Air-Stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes

  摘要：

  The synthesis and characterization of the air-stable nickel(II) complex trans-(PCy2Ph)(2)Ni(o-tolyl)Cl is described in conjunction with an investigation of its use for the Mizoroki-Heck-type, room temperature, internally selective coupling of substituted benzyl chlorides with terminal alkenes. This reaction, which employs a terminal alkene as an alkenylmetal equivalent, provides rapid, convergent access to substituted allylbenzene derivatives in high yield and with regioselectivity greater than 95:5 in nearly all cases. The reaction is operationally simple, can be carried out on the benchtop with no purification or degassing of solvents or reagents, and requires no exclusion of air or water during setup. Synthesis of the precatalyst is accomplished through a straightforward procedure that employs inexpensive, commercially available reagents, requires no purification steps, and proceeds in high yield.

  DOI：

  10.1021/ja3116718

文献信息

• [EN] NICKEL PRE-CATALYSTS AND RELATED COMPOSITIONS AND METHODS<br/>[FR] PRÉ-CATALYSEURS DE NICKEL ET COMPOSITIONS ET MÉTHODES ASSOCIÉES
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2015070026A1

  公开（公告）日：2015-05-14

  Described herein are nickel pre-catalysts and related compositions and methods. The nickel pre-catalysts may be activated to form catalysts which may be utilized in organic reactions.

  本文描述了镍前催化剂及相关组成物和方法。这些镍前催化剂可以被活化形成催化剂，可用于有机反应中。
• Simplifying Nickel(0) Catalysis: An Air-Stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes
  作者：Eric A. Standley、Timothy F. Jamison

  DOI：10.1021/ja3116718

  日期：2013.1.30

  The synthesis and characterization of the air-stable nickel(II) complex trans-(PCy2Ph)(2)Ni(o-tolyl)Cl is described in conjunction with an investigation of its use for the Mizoroki-Heck-type, room temperature, internally selective coupling of substituted benzyl chlorides with terminal alkenes. This reaction, which employs a terminal alkene as an alkenylmetal equivalent, provides rapid, convergent access to substituted allylbenzene derivatives in high yield and with regioselectivity greater than 95:5 in nearly all cases. The reaction is operationally simple, can be carried out on the benchtop with no purification or degassing of solvents or reagents, and requires no exclusion of air or water during setup. Synthesis of the precatalyst is accomplished through a straightforward procedure that employs inexpensive, commercially available reagents, requires no purification steps, and proceeds in high yield.