2,3,4,5-Tetrahydrobenzo[h][1]benzoxepine-6,11-dione | 13625-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3,4,5-Tetrahydrobenzo[h][1]benzoxepine-6,11-dione
• 英文别名: 2,3,4,5-tetrahydrobenzo[h][1]benzoxepine-6,11-dione
• CAS: 13625-06-4
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: UJGBCMMOOQSBMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,2,4-三甲氧基萘 在 正丁基锂 、 ammonium cerium (IV) nitrate 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 水 、 乙腈 为溶剂， 反应 69.17h， 生成 、 、 2,3,4,5-Tetrahydrobenzo[i][1]benzoxepine-6,7-dione 、 2,3,4,5-Tetrahydrobenzo[h][1]benzoxepine-6,11-dione
  参考文献：
  名称：

  Studies on the oxidative cyclization of 3-hydroxyalkyl-1,2,4-trialkoxynaphthalenes and synthetic application for the biologically active natural compound rhinacanthone

  摘要：

  The oxidative intramolecular cyclization of 3-hydroxyalkyl-1,2,4-trimethoxynaphthalenes was investigated. A series of 1,2-naphthoquinone fused cyclic ethers were synthesized directly from 3-hydroxyalkyl-1,2,4-trimethoxynaphthalenes by exposure to diammonium cerium (IV) nitrate. To understand the reaction mechanism, the intramolecular cyclization of 3-hydroxyalkyl-naphthoquinones that were formed as reaction intermediates was also examined. The results suggested that the reaction proceeds by a stepwise oxidation-cyclization mechanism. Using this methodology, five-step synthesis of rhinacanthone was achieved with high yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.025

文献信息

• Studies on the oxidative cyclization of 3-hydroxyalkyl-1,2,4-trialkoxynaphthalenes and synthetic application for the biologically active natural compound rhinacanthone
  作者：Tokutaro Ogata、Misae Doe、Aya Matsubara、Eri Torii、Chiaki Nishiura、Arisa Nishiuchi、Yusuke Kobayashi、Tetsutaro Kimachi

  DOI：10.1016/j.tet.2013.11.025

  日期：2014.1

  The oxidative intramolecular cyclization of 3-hydroxyalkyl-1,2,4-trimethoxynaphthalenes was investigated. A series of 1,2-naphthoquinone fused cyclic ethers were synthesized directly from 3-hydroxyalkyl-1,2,4-trimethoxynaphthalenes by exposure to diammonium cerium (IV) nitrate. To understand the reaction mechanism, the intramolecular cyclization of 3-hydroxyalkyl-naphthoquinones that were formed as reaction intermediates was also examined. The results suggested that the reaction proceeds by a stepwise oxidation-cyclization mechanism. Using this methodology, five-step synthesis of rhinacanthone was achieved with high yield. (C) 2013 Elsevier Ltd. All rights reserved.