5-Hydroxymethyl-4-aza-tricyclo[5.2.2.02,6]undeca-2,5,8-triene-3-carboxylic acid ethyl ester | 736181-64-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 5-Hydroxymethyl-4-aza-tricyclo[5.2.2.02,6]undeca-2,5,8-triene-3-carboxylic acid ethyl ester
• 英文别名: 5-Hydroxymethyl-4-aza-tricyclo[5.2.2.0^2,6]undeca-2,5,8-triene-3-carboxylic acid ethyl ester
• CAS: 736181-64-9
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: SLTACHDMUGIXOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.32
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 5-Hydroxymethyl-4-aza-tricyclo[5.2.2.02,6]undeca-2,5,8-triene-3-carboxylic acid ethyl ester 在 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 生成 ethyl 3-acetoxylmethyl-4,7-dihydro-4,7-ethano-2H-isoindole-1-carboxylate
  参考文献：
  名称：

  An efficient synthesis of conjugation-expanded carba- and azuliporphyrins using a bicyclo[2.2.2]octadiene-fused tripyrrane

  摘要：

  A bicyclo[2.2.2]octadiene-fused tripyrrane was synthesized as a first versatile reagent for the preparation of pi-expanded heteroporphyrins. The reaction of the tripyrrane with 1,3-diformylindene and azulene-1,3-dicarbaldehyde afforded the corresponding heteroporphyrins. which were easily converted into tetrabenzocarbaporphyrin and tribenzoazuliporphyrin by retro Diels-Alder reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.041
• 作为产物：
  描述：

  ethyl 4,7-dihydro-4,7-ethano-2H-isoindole-1-carboxylate 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-Hydroxymethyl-4-aza-tricyclo[5.2.2.02,6]undeca-2,5,8-triene-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  An efficient synthesis of conjugation-expanded carba- and azuliporphyrins using a bicyclo[2.2.2]octadiene-fused tripyrrane

  摘要：

  A bicyclo[2.2.2]octadiene-fused tripyrrane was synthesized as a first versatile reagent for the preparation of pi-expanded heteroporphyrins. The reaction of the tripyrrane with 1,3-diformylindene and azulene-1,3-dicarbaldehyde afforded the corresponding heteroporphyrins. which were easily converted into tetrabenzocarbaporphyrin and tribenzoazuliporphyrin by retro Diels-Alder reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.041