2-{[2-(cyclohexa-1,4-dienyl)ethylamino]methylene}malonic acid diethyl ester | 882522-76-1

• 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: 2-{[2-(cyclohexa-1,4-dienyl)ethylamino]methylene}malonic acid diethyl ester
• 英文别名: Diethyl 2-[(2-cyclohexa-1,4-dien-1-ylethylamino)methylidene]propanedioate；diethyl 2-[(2-cyclohexa-1,4-dien-1-ylethylamino)methylidene]propanedioate
• CAS: 882522-76-1
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: URPBNBKSHVGYEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-{[2-(cyclohexa-1,4-dienyl)ethylamino]methylene}malonic acid diethyl ester 在 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 31.0h， 生成 (3aRS,4aRS,8aRS)-1,2,5,8-tetrahydro-3aH,4aH-3-azacyclopenta[1,4]cyclobuta[1,2]benzene-3,4,4-tricarboxylic acid 3-tert-butyl ester 4,4-diethyl ester
  参考文献：
  名称：

  Tandem Photocycloaddition−Retro-Mannich Fragmentation of Enaminones. A Route to Spiropyrrolines and the Tetracyclic Core of Koumine

  摘要：

  Intramolecular [2 + 2] photocycloaddition of beta-aminoalkylidene malonates gives transiently a cyclobutane which undergoes retro-Mannich fragmentation to a Delta(1)-pyrroline. The tandem sequence, exemplified in two series based on tryptamine and aminoethyl-1,4-cyclohexadiene, leads to a spiroindolopyrroline skeleton and to the nonindolenine portion of koumine.

  DOI：

  10.1021/ol052955y
• 作为产物：
  描述：

  2-(cyclohexa-1,4-dien-1-yl)ethan-1-amine 、 乙氧基甲叉丙二酸二乙酯 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 26.0h， 以99%的产率得到2-{[2-(cyclohexa-1,4-dienyl)ethylamino]methylene}malonic acid diethyl ester
  参考文献：
  名称：

  Tandem Photocycloaddition−Retro-Mannich Fragmentation of Enaminones. A Route to Spiropyrrolines and the Tetracyclic Core of Koumine

  摘要：

  Intramolecular [2 + 2] photocycloaddition of beta-aminoalkylidene malonates gives transiently a cyclobutane which undergoes retro-Mannich fragmentation to a Delta(1)-pyrroline. The tandem sequence, exemplified in two series based on tryptamine and aminoethyl-1,4-cyclohexadiene, leads to a spiroindolopyrroline skeleton and to the nonindolenine portion of koumine.

  DOI：

  10.1021/ol052955y

文献信息

• Tandem Photocycloaddition−Retro-Mannich Fragmentation of Enaminones. A Route to Spiropyrrolines and the Tetracyclic Core of Koumine
  作者：James D. White、David C. Ihle

  DOI：10.1021/ol052955y

  日期：2006.3.1

  Intramolecular [2 + 2] photocycloaddition of beta-aminoalkylidene malonates gives transiently a cyclobutane which undergoes retro-Mannich fragmentation to a Delta(1)-pyrroline. The tandem sequence, exemplified in two series based on tryptamine and aminoethyl-1,4-cyclohexadiene, leads to a spiroindolopyrroline skeleton and to the nonindolenine portion of koumine.