ethyl 4,11-dihydro-4,11-ethanoanthra[2,3-c]pyrrole-1-carboxylate | 1041181-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: ethyl 4,11-dihydro-4,11-ethanoanthra[2,3-c]pyrrole-1-carboxylate
• 英文别名: Ethyl 15-azapentacyclo[10.5.2.02,11.04,9.013,17]nonadeca-2,4,6,8,10,13,16-heptaene-14-carboxylate；ethyl 15-azapentacyclo[10.5.2.02,11.04,9.013,17]nonadeca-2,4,6,8,10,13,16-heptaene-14-carboxylate
• CAS: 1041181-06-9
• 化学式: C₂₁H₁₉NO₂
• 分子量: 317.387
• InChiKey: HIUOXCWKGDYBAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 4,11-dihydro-4,11-ethanoanthra[2,3-c]pyrrole-1-carboxylate 在 potassium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 2.0h， 以67%的产率得到4,11-dihydro-4,11-ethano-2H-naphth[2,3f]isoindole
  参考文献：
  名称：

  Thermal Behavior of Bicyclo[2.2.2]octadiene-Installed Precursors for 2H-Anthra[2,3-c]pyrroles and Anthra[2,3-c]thiophene

  摘要：

  4,11-Ethano-4,11-dihydro-2H-anthra[2,3-c]pyrrole and 4,11-ethano-4,11-dihydroanthra[2,3-c]thiophene derivatives were prepared from the corresponding bicyclo[2.2.2]octadiene-fused five-membered heterocycles by the Diels-Alder reaction with in situ generated alpha, alpha'-dibromo-o-xylylene derivatives. Their thermogravimetric analyses showed evapolation without formation of 2H-anthra[2,3-c]pyrrole and anthra[2,3-c]thiophene derivatives under the atmospheric pressure.

  DOI：

  10.3987/com-09-s(s)102
• 作为产物：
  描述：

  四溴对烯 、 ethyl 4,7-dihydro-4,7-ethano-2H-isoindole-1-carboxylate 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以18%的产率得到ethyl 4,11-dihydro-4,11-ethanoanthra[2,3-c]pyrrole-1-carboxylate
  参考文献：
  名称：

  Thermal Behavior of Bicyclo[2.2.2]octadiene-Installed Precursors for 2H-Anthra[2,3-c]pyrroles and Anthra[2,3-c]thiophene

  摘要：

  4,11-Ethano-4,11-dihydro-2H-anthra[2,3-c]pyrrole and 4,11-ethano-4,11-dihydroanthra[2,3-c]thiophene derivatives were prepared from the corresponding bicyclo[2.2.2]octadiene-fused five-membered heterocycles by the Diels-Alder reaction with in situ generated alpha, alpha'-dibromo-o-xylylene derivatives. Their thermogravimetric analyses showed evapolation without formation of 2H-anthra[2,3-c]pyrrole and anthra[2,3-c]thiophene derivatives under the atmospheric pressure.

  DOI：

  10.3987/com-09-s(s)102

文献信息

• Synthesis of π-conjugated asymmetric aza-BODIPYs via nitrosobicyclopyrroles
  作者：Ryota Mori、Minenari Asakura、Yukinori Kobayashi、Hiromu Mashimo、Makoto Roppongi、Satoshi Ito

  DOI：10.1016/j.tetlet.2022.153759

  日期：2022.4

  π-Conjugated aza-BODIPYs with absorption in the near-infrared region have attracted attention, but there are few reports of their synthesis. We report the synthesis and absorption properties of π-conjugated asymmetric aza-BODIPYs by nitrosation and retro-Diels-Alder reaction of bicyclo[2.2.2]octadiene-fused bicyclopyrroles. We also synthesized aza-BODIPY fused with [2.3]naphtho and [2.3]anthra structures

  在近红外区域具有吸收的π-共轭氮杂-BODIPYs引起了人们的关注，但对其合成的报道很少。我们报告了通过双环[2.2.2]辛二烯稠合双环吡咯的亚硝化和逆-Diels-Alder 反应合成π-共轭不对称氮杂-BODIPYs 的性质和吸收性能。我们还首次通过该方法合成了融合[2.3]萘和[2.3]蒽结构的aza-BODIPY和π-共轭氮杂-O-螯合物BODIPY。
• Synthesis and Characterization of Tetraanthroporphyrins
  作者：Hiroko Yamada、Daiki Kuzuhara、Tetsuro Takahashi、Yusuke Shimizu、Keisuke Uota、Tetsuo Okujima、Hidemitsu Uno、Noboru Ono

  DOI：10.1021/ol8008842

  日期：2008.7.17

  Linearly pi-expanded novel tetraanthroporphyrins with and without aromatic rings at the meso-positions were prepared quantitatively for the first time from the corresponding precursors by a retro-Diels-Alder reaction.
• Thermal Behavior of Bicyclo[2.2.2]octadiene-Installed Precursors for 2H-Anthra[2,3-c]pyrroles and Anthra[2,3-c]thiophene
  作者：Hidemitsu Uno、Hiroki Uoyama、Cai Chenxin、Hiroyuki Tahara、Yusuke Shimizu、Hideki Hagiwara、Yasuaki Hanasaki、Hiroko Yamada、Tetsuo Okujima

  DOI：10.3987/com-09-s(s)102

  日期：——

  4,11-Ethano-4,11-dihydro-2H-anthra[2,3-c]pyrrole and 4,11-ethano-4,11-dihydroanthra[2,3-c]thiophene derivatives were prepared from the corresponding bicyclo[2.2.2]octadiene-fused five-membered heterocycles by the Diels-Alder reaction with in situ generated alpha, alpha'-dibromo-o-xylylene derivatives. Their thermogravimetric analyses showed evapolation without formation of 2H-anthra[2,3-c]pyrrole and anthra[2,3-c]thiophene derivatives under the atmospheric pressure.