but-3-yn-2-yl 3-bromopropiolate | 1397708-07-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: but-3-yn-2-yl 3-bromopropiolate
• 英文别名: But-3-yn-2-yl 3-bromoprop-2-ynoate
• CAS: 1397708-07-4
• 化学式: C₇H₅BrO₂
• 分子量: 201.019
• InChiKey: OTINCBVHEYALNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  but-3-yn-2-yl 3-bromopropiolate 、 三甲基乙炔基硅 在 chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 20.0h， 以64%的产率得到7-bromo-3-methyl-5-(trimethylsilyl)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  Cyclotrimerization of unsymmetrically bromo-substituted diynes: toward the synthesis of potential selective inhibitors of tyrosine kinase 2

  摘要：

  A study on transition metal catalyzed alkyne cyclotrimerization of unsymmetrically bromo-substituted diynes with ethynyltrimethylsilane was carried out to prepare bicyclic bromobenzene key intermediates for the total synthesis of five potential tyrosine kinase 2 inhibitors. Two different pre-catalysts (Cp*RuCl(cod) and [Rh(cod)(2)]BF4/BINAP) and different reaction conditions have been examined. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.087
• 作为产物：
  描述：

  4-(trimethylsilyl)but-3-yn-2-yl 3-bromopropiolate 在 水 、 silver nitrate 作用下， 以 丙酮 为溶剂， 反应 20.0h， 以89%的产率得到but-3-yn-2-yl 3-bromopropiolate
  参考文献：
  名称：

  Cyclotrimerization of unsymmetrically bromo-substituted diynes: toward the synthesis of potential selective inhibitors of tyrosine kinase 2

  摘要：

  A study on transition metal catalyzed alkyne cyclotrimerization of unsymmetrically bromo-substituted diynes with ethynyltrimethylsilane was carried out to prepare bicyclic bromobenzene key intermediates for the total synthesis of five potential tyrosine kinase 2 inhibitors. Two different pre-catalysts (Cp*RuCl(cod) and [Rh(cod)(2)]BF4/BINAP) and different reaction conditions have been examined. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.087

文献信息

• Aryl N-methyliminodiacetic acid (MIDA) boronates from cyclotrimerization of ethynyl MIDA boronate with diynes
  作者：Silje Melnes、Annette Bayer、Odd R. Gautun

  DOI：10.1016/j.tet.2013.07.027

  日期：2013.9

  Cyclotrimerizations of ethynyl N-methyliminodiacetic acid (MIDA) boronate (1) with 1,6-diynes 2 have been studied, using three different catalysts (based on ruthenium, rhodium, and iridium) and variable reaction conditions. Successful cyclotrimerization reactions were obtained with both Cp*RuCl(cod) and Rh(cod)2BF4/BINAP as pre-catalysts in THF or acetone. Ruthenium-catalyzed cyclotrimerization of

  使用三种不同的催化剂（基于钌，铑和铱）和可变的反应条件，研究了乙炔基N-甲基亚氨基二乙酸（MIDA）硼酸酯（1）与1,6-二炔2的环三聚反应。使用Cp * RuCl（cod）和Rh（cod）2 BF 4 / BINAP作为四氢呋喃或丙酮的预催化剂，成功地完成了环三聚反应。钌催化的不对称溴取代的二炔（2f）与1的钌催化环三聚反应成功扩大规模（2 g），并包括在针对酪氨酸激酶2潜在选择性抑制剂的总合成策略中。