5-Formyl-4-aza-tricyclo[5.2.2.0^2,6]undeca-2,5,8-triene-3-carboxylic acid ethyl ester | 736181-63-8

• 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-Formyl-4-aza-tricyclo[5.2.2.0^2,6]undeca-2,5,8-triene-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 5-formyl-4-azatricyclo[5.2.2.02,6]undeca-2,5,8-triene-3-carboxylate
• CAS: 736181-63-8
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: UHBYCEXILHHGDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Formyl-4-aza-tricyclo[5.2.2.0^2,6]undeca-2,5,8-triene-3-carboxylic acid ethyl ester 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 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：

  N,N-二甲基甲酰胺 、 ethyl 4,7-dihydro-4,7-ethano-2H-isoindole-1-carboxylate 在 三氯氧磷 作用下， 反应 3.0h， 以96%的产率得到5-Formyl-4-aza-tricyclo[5.2.2.0^2,6]undeca-2,5,8-triene-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  使用超临界二氧化碳高效合成异吲哚

  摘要：

  通过在超临界二氧化碳中的逆狄尔斯-阿尔德反应，将双环吡咯有效地转化为相应的异吲哚。通过添加乙烯气体作为除氧剂，异吲哚的收率进一步提高。

  DOI：

  10.1016/j.tetlet.2017.02.055

文献信息

• METHOD FOR PRODUCING ISOINDOLE
  申请人：Ito Satoshi

  公开号：US20110137024A1

  公开（公告）日：2011-06-09

  Disclosed is a method for manufacturing isoindolic compound, which can adopt a condition capable of being put to industrially practical use, which can produce stable isoindolic compound, and which can further produce the isoindolic compound with a high yield. The method for manufacturing isoindolic compound comprises a thermal treatment step where a compound of which molecule includes a structure of pyrrole fused with bicyclo [2.2.2] octadiene skeleton is subjected to a supercritical carbon dioxide atmosphere. The thermal treatment step is preferably performed at a temperature of not less than 50° C. and not more than 300° C.
• US8481753B2
  申请人：——

  公开号：US8481753B2

  公开（公告）日：2013-07-09
• Efficient synthesis of isoindoles using supercritical carbon dioxide
  作者：Satoshi Ito、Masayuki Akaki、Yasutaka Shinozaki、Yuuki Iwabe、Masaru Furuya、Marina Tobata、Makoto Roppongi、Takafumi Sato、Naotsugu Itoh、Toru Oba

  DOI：10.1016/j.tetlet.2017.02.055

  日期：2017.3

  Bicyclopyrroles were efficiently converted to the corresponding isoindoles by a retro Diels-Alder reaction in supercritical carbon dioxide. By adding ethylene gas as an oxygen scavenger, the isoindole yield was further improved.

  通过在超临界二氧化碳中的逆狄尔斯-阿尔德反应，将双环吡咯有效地转化为相应的异吲哚。通过添加乙烯气体作为除氧剂，异吲哚的收率进一步提高。
• An efficient synthesis of conjugation-expanded carba- and azuliporphyrins using a bicyclo[2.2.2]octadiene-fused tripyrrane
  作者：Tetsuo Okujima、Naoki Komobuchi、Yusuke Shimizu、Hidemitsu Uno、Noboru Ono

  DOI：10.1016/j.tetlet.2004.05.041

  日期：2004.7

  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.