tert-butyldimethyl-[4-(1,3,4-trimethoxynaphthalen-2-yl)-butoxy]-silane | 1526990-25-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyldimethyl-[4-(1,3,4-trimethoxynaphthalen-2-yl)-butoxy]-silane
• CAS: 1526990-25-9
• 化学式: C₂₃H₃₆O₄Si
• 分子量: 404.622
• InChiKey: KKUDFVXJPGBCPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyldimethyl-[4-(1,3,4-trimethoxynaphthalen-2-yl)-butoxy]-silane 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 18.67h， 以84%的产率得到4-(1,3,4-trimethoxynaphthalen-2-yl)-butanol
  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 、 (4-溴丁氧基)叔丁基二甲基硅烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 50.0h， 以70%的产率得到tert-butyldimethyl-[4-(1,3,4-trimethoxynaphthalen-2-yl)-butoxy]-silane
  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