methyl 2-diazo-4-[2-(1-benzyloxycarbonyl-1,2-dihydro)quinoline]-3-oxobutyrate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: methyl 2-diazo-4-[2-(1-benzyloxycarbonyl-1,2-dihydro)quinoline]-3-oxobutyrate
• 英文别名: benzyl 2-(3-diazo-4-methoxy-2,4-dioxobutyl)-2H-quinoline-1-carboxylate
• 化学式: C₂₂H₁₉N₃O₅
• 分子量: 405.41
• InChiKey: BHIGYHNYMBCFOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-diazo-4-[2-(1-benzyloxycarbonyl-1,2-dihydro)quinoline]-3-oxobutyrate 在 dirhodium tetraacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 以100%的产率得到3-benzyl 7c-methyl 1-oxo-1,2,2a,7c-tetrahydro-7bH-bicyclo[3.1.0]hex-5-eno[4,5,6-bc]quinoline-3,7c(8H)-dicarboxylate
  参考文献：
  名称：

  An efficient route for the construction of cyclopenta[b]quinoline derivatives via intramolecular cyclopropanation

  摘要：

  A one-pot process to introduce diazoacetoacetate functionality into quinoline was identified with excellent yield and regioselectivity. An intramolecular cyclopropanation of the resulting adducts gave tetracyclic cyclopenta[b]quinoline derivatives in nearly quantitative yields. A synthetic utility of the tetracyclic derivatives was examined by a simple ring opening reaction to afford cyclopenta[ b] quinoline in a good yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.034
• 作为产物：
  描述：

  喹啉 、 2-Diazo-3-oxo-butyric acid methyl ester 、 氯甲酸苄酯 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到methyl 2-diazo-4-[2-(1-benzyloxycarbonyl-1,2-dihydro)quinoline]-3-oxobutyrate
  参考文献：
  名称：

  An efficient route for the construction of cyclopenta[b]quinoline derivatives via intramolecular cyclopropanation

  摘要：

  A one-pot process to introduce diazoacetoacetate functionality into quinoline was identified with excellent yield and regioselectivity. An intramolecular cyclopropanation of the resulting adducts gave tetracyclic cyclopenta[b]quinoline derivatives in nearly quantitative yields. A synthetic utility of the tetracyclic derivatives was examined by a simple ring opening reaction to afford cyclopenta[ b] quinoline in a good yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.034

文献信息

• An efficient route for the construction of cyclopenta[b]quinoline derivatives via intramolecular cyclopropanation
  作者：Haoxi Huang、Wenhao Hu

  DOI：10.1016/j.tet.2007.09.034

  日期：2007.11

  A one-pot process to introduce diazoacetoacetate functionality into quinoline was identified with excellent yield and regioselectivity. An intramolecular cyclopropanation of the resulting adducts gave tetracyclic cyclopenta[b]quinoline derivatives in nearly quantitative yields. A synthetic utility of the tetracyclic derivatives was examined by a simple ring opening reaction to afford cyclopenta[ b] quinoline in a good yield. (c) 2007 Elsevier Ltd. All rights reserved.