3-(1,3,4-trimethoxynaphthalen-2-yl)-propan-1-ol | 1526990-24-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(1,3,4-trimethoxynaphthalen-2-yl)-propan-1-ol
• 英文别名: 3-(1,3,4-Trimethoxynaphthalen-2-yl)propan-1-ol；3-(1,3,4-trimethoxynaphthalen-2-yl)propan-1-ol
• CAS: 1526990-24-8
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: RWJODERFPJCXKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1,3,4-trimethoxynaphthalen-2-yl)-propan-1-ol 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以67%的产率得到3,4-dihydro-2H-benzo[h]chromene-5,6-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
• 作为产物：
  描述：

  1,2,4-三甲氧基萘 在 正丁基锂 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 17.67h， 生成 3-(1,3,4-trimethoxynaphthalen-2-yl)-propan-1-ol
  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.