(E)-methyl 2-diazo-4-(benzofuran-2-yl)but-3-enoate | 888223-30-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (E)-methyl 2-diazo-4-(benzofuran-2-yl)but-3-enoate
• CAS: 888223-30-1
• 化学式: C₁₃H₁₀N₂O₃
• 分子量: 242.234
• InChiKey: WIUYWQOHPGTISU-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  75.84
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-methyl 2-diazo-4-(benzofuran-2-yl)but-3-enoate 、 3,4-dihydronaphthalen-1-yl acetate 在 dirhodium (S)-tetrakis(N-(dodecylbenzenesulfonyl)prolinate) 作用下， 以 正己烷 、 甲苯 为溶剂， 以60%的产率得到(R,E)-methyl 4-(benzofuran-2-yl)-4-(naphthalen-5-yl)but-2-enoate
  参考文献：
  名称：

  Direct synthesis of methyl 2-diazo-4-aryl-3-butenoates and their application to the enantioselective synthesis of 4-aryl-4-(1-naphthyl)-2-butenoates

  摘要：

  An improved one-flask synthesis of various methyl 2-diazo-4-aryl and 4-heteroaryl-3-butenoates, precursors to donor/ acceptor Substituted carbenoids, is described. Their Rh-2(S-DOSP)(4) catalyzed reaction with 1-acetoxy-3,4-diliydronaphthalene, via a combined C-H activation/Cope rearrangement pathway followed by elimination of acetic acid affords a highly enantioselective (98-99% ee) entry to methyl 4-aryl- and 4-heteroaryl-4-(1-naphthyl)-2-butenoates. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.01.023
• 作为产物：
  描述：

  (E)-4-Benzofuran-2-yl-but-3-enoic acid methyl ester 在 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以0.363 g的产率得到(E)-methyl 2-diazo-4-(benzofuran-2-yl)but-3-enoate
  参考文献：
  名称：

  Direct synthesis of methyl 2-diazo-4-aryl-3-butenoates and their application to the enantioselective synthesis of 4-aryl-4-(1-naphthyl)-2-butenoates

  摘要：

  An improved one-flask synthesis of various methyl 2-diazo-4-aryl and 4-heteroaryl-3-butenoates, precursors to donor/ acceptor Substituted carbenoids, is described. Their Rh-2(S-DOSP)(4) catalyzed reaction with 1-acetoxy-3,4-diliydronaphthalene, via a combined C-H activation/Cope rearrangement pathway followed by elimination of acetic acid affords a highly enantioselective (98-99% ee) entry to methyl 4-aryl- and 4-heteroaryl-4-(1-naphthyl)-2-butenoates. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.01.023

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。