(E)-methyl 2-diazo-4-(5-bromothiophen-2-yl)but-3-enoate | 1039434-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (E)-methyl 2-diazo-4-(5-bromothiophen-2-yl)but-3-enoate
• CAS: 1039434-28-0
• 化学式: C₉H₇BrN₂O₂S
• 分子量: 287.137
• InChiKey: DRRVPEKAJPJQJT-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  62.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,4-dihydronaphthalen-1-yl acetate 、 (E)-methyl 2-diazo-4-(5-bromothiophen-2-yl)but-3-enoate 在 Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 0.58h， 以85%的产率得到(R,E)-methyl 4-(5-bromothiophen-2-yl)-4-(naphthalen-1-yl)but-2-enoate
  参考文献：
  名称：

  1-Naphthyl and 4-indolyl arylalkylamines as selective monoamine reuptake inhibitors

  摘要：

  A series of enantiomerically pure 1-naphthyl and 4-indolyl arylalkylamines were prepared and evaluated for their binding affinities to the monoamine transporters. The two series of enantiomers displayed considerable differences in binding selectivity between the monoamine transporters, leading to the design of (S)-4-(3,4-dichlorophenyl)-4-(1H-indol-4-yl)-N-methylbutan-1-amine as a potent inhibitor for the dopamine and serotonin transporters. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.022

文献信息

• One-Pot Synthesis of Highly Functionalized Pyridines via a Rhodium Carbenoid Induced Ring Expansion of Isoxazoles
  作者：James R. Manning、Huw M. L. Davies

  DOI：10.1021/ja803139k

  日期：2008.7.1

  A concise one-pot synthesis of highly functionalized pyridines has been developed. The first step in the reaction sequence is the formal insertion of rhodium vinylcarbenoids across the N-O bond of isoxazoles. Upon heating, the insertion products undergo a rearrangement to give 1,4-dihydropyridines. DDQ oxidation then affords the corresponding pyridines in 31-84% yield. The process has proven general

  已开发出高度官能化吡啶的简洁一锅法合成。反应序列中的第一步是将乙烯基卡宾铑正式插入到异恶唑的 NO 键上。加热后，插入产物发生重排，得到 1,4-二氢吡啶。然后DDQ氧化以31-84%的产率提供相应的吡啶。该过程已被证明适用于一系列类卡宾和异恶唑组分，并代表了合成功能化吡啶的独特断开策略。