11-naphthalen-2-yl-9-(toluene-4-sulfonyl)-9,10-dihydro-8H-9-azacyclopenta[b]phenanthrene | 1617506-56-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 11-naphthalen-2-yl-9-(toluene-4-sulfonyl)-9,10-dihydro-8H-9-azacyclopenta[b]phenanthrene
• 英文别名: 9-(4-Methylphenyl)sulfonyl-11-naphthalen-2-yl-8,10-dihydronaphtho[1,2-f]isoindole；9-(4-methylphenyl)sulfonyl-11-naphthalen-2-yl-8,10-dihydronaphtho[1,2-f]isoindole
• CAS: 1617506-56-5
• 化学式: C₃₃H₂₅NO₂S
• 分子量: 499.633
• InChiKey: DMEWQPZFSJMIPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  C₃₃H₂₅NO₂S 在 aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到11-naphthalen-2-yl-9-(toluene-4-sulfonyl)-9,10-dihydro-8H-9-azacyclopenta[b]phenanthrene
  参考文献：
  名称：

  Garratt–Braverman cyclization on basic alumina: a green protocol with improved selectivity

  摘要：

  A green protocol (compared to the existing methodology) for carrying out Garratt-Braverman cyclization has been developed. The method involves stirring a pre-absorbed bispropargyl sulfone/ether/sulfonamide over basic alumina. The reaction with sulfones was over within 10-15 mm at room temperature whereas for the ether/sulfonamide the reaction took 6-8 h at 130 degrees C. The products, aryl naphthalene derivatives, are obtained by simple filtration through Celite, in excellent yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.033

文献信息

• Sonogashira coupling and Garratt–Braverman cyclization in tandem: formation of four C–C bonds leading to the synthesis of aryl dihydro isofurans and isoindoles
  作者：Debaki Ghosh、Paramita Pal、Amit Basak

  DOI：10.1016/j.tetlet.2015.02.093

  日期：2015.4

  In this Letter we report an interesting one pot synthesis of aryl dihydro isofurans and isoindoles, naturally occurring privileged skeletons, in excellent yields from easily accessible starting materials. The process involved carrying out three reactions in a tandem manner leading to 4 C-C bond formations, namely two Sonogashira couplings (2 x 1 C-C bond) followed by Garratt-Braverman Cyclization (2 C-C bond). (C) 2015 Elsevier Ltd. All rights reserved.
• Garratt–Braverman cyclization on basic alumina: a green protocol with improved selectivity
  作者：Debaki Ghosh、Subhanip Biswas、Koena Ghosh、Amit Basak

  DOI：10.1016/j.tetlet.2014.05.033

  日期：2014.7

  A green protocol (compared to the existing methodology) for carrying out Garratt-Braverman cyclization has been developed. The method involves stirring a pre-absorbed bispropargyl sulfone/ether/sulfonamide over basic alumina. The reaction with sulfones was over within 10-15 mm at room temperature whereas for the ether/sulfonamide the reaction took 6-8 h at 130 degrees C. The products, aryl naphthalene derivatives, are obtained by simple filtration through Celite, in excellent yields. (C) 2014 Elsevier Ltd. All rights reserved.