3-Methyl-2-oxo-1,2,4,6,7,7a-hexahydro-indene-5,5-dicarboxylic acid diethyl ester | 143633-95-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-Methyl-2-oxo-1,2,4,6,7,7a-hexahydro-indene-5,5-dicarboxylic acid diethyl ester
• 英文别名: diethyl 3-methyl-2-oxo-4,6,7,7a-tetrahydro-1H-indene-5,5-dicarboxylate
• CAS: 143633-95-8
• 化学式: C₁₆H₂₂O₅
• 分子量: 294.348
• InChiKey: IJQWMYRTMDGGOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  一氧化碳 、 Diethyl 2-but-3-enyl-2-but-2-ynylpropanedioate 在 二氯二茂钛 、 乙基溴化镁 作用下， 生成 3-Methyl-2-oxo-1,2,4,6,7,7a-hexahydro-indene-5,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Reductive cyclization of ester-containing enynes with a practical titanocene reagent. Synthesis of bicyclic cyclopentenones and iminocyclopentenes

  摘要：

  The combination of Cp2TiCl2 with 2 equiv of EtMgBr provides an effective reagent for the reductive cyclization of enynes, including ester-containing enynes, to bicyclic titanacyclopentenes. These metallacycles may then be transformed into bicyclic cyclopentenones or iminocyclopentenes in good yields by reaction with CO or an isocyanide, respectively.

  DOI：

  10.1021/jo00048a001

文献信息

• Mild and Efficient Molybdenum-Mediated Pauson−Khand-Type Reaction
  作者：Javier Adrio、Marta Rodríguez Rivero、Juan Carlos Carretero

  DOI：10.1021/ol047678u

  日期：2005.2.1

  Pauson-Khand reaction promoted by Mo(CO)3(DMF)3 takes place under very mild conditions in the absence of any promoter. High yields in Pauson-Khand adducts are obtained in the cyclization of a wide variety of functionalized 1,6- and 1,7-enynes. Enynes bearing electron withdrawing groups at the alkene terminus are particularly good substrates.

  [反应：见正文]由Mo（CO）3（DMF）3促进的钼介导的Pauson-Khand反应在非常温和的条件下发生，没有任何启动子。在多种功能化的1,6-和1,7-烯炔的环化反应中，Pauson-Khand加合物的收率很高。在烯烃末端带有吸电子基团的烯炔是特别好的底物。
• Reductive cyclization of ester-containing enynes with a practical titanocene reagent. Synthesis of bicyclic cyclopentenones and iminocyclopentenes
  作者：Robert B. Grossman、Stephen L. Buchwald

  DOI：10.1021/jo00048a001

  日期：1992.10

  The combination of Cp2TiCl2 with 2 equiv of EtMgBr provides an effective reagent for the reductive cyclization of enynes, including ester-containing enynes, to bicyclic titanacyclopentenes. These metallacycles may then be transformed into bicyclic cyclopentenones or iminocyclopentenes in good yields by reaction with CO or an isocyanide, respectively.