(1R,3S)-ethyl 5-bromo-3-(((tert-butyldimethylsilyl)oxy)-methyl)-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate | 1448530-86-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,3S)-ethyl 5-bromo-3-(((tert-butyldimethylsilyl)oxy)-methyl)-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate
• 英文别名: ethyl (1S,3S)-5-bromo-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate
• CAS: 1448530-86-6
• 化学式: C₂₁H₃₄BrNO₅Si
• 分子量: 488.494
• InChiKey: CLRAOZREHVBOJX-GUYCJALGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,3S)-ethyl 5-bromo-3-(((tert-butyldimethylsilyl)oxy)-methyl)-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate 在 草酰氯 、 20% palladium hydroxide-activated charcoal 、 四丁基氟化铵 、 氢气 、 potassium carbonate 、 二甲基亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， -78.0 ℃ 、344.75 kPa 条件下， 反应 61.25h， 生成 (1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate
  参考文献：
  名称：

  Synthetic studies on lemonomycin: construction of the tetracyclic core

  摘要：

  A substrate-induced stereocontrol strategy was used to gain access to the tetracyclic core of (-)-lemonomycin. An advanced intermediate was prepared from a known substituted tyrosinol through a 16-step sequence, which involved a Pictet-Spengler reaction, a [3+2] dipolar cycloaddition and an enamide hydrogenation. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.05.009
• 作为产物：
  描述：

  bromotyrosinol 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 氯化铵 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 2,2,2-三氟乙醇 、 水 、 甲苯 为溶剂， 反应 5.42h， 生成 (1R,3S)-ethyl 5-bromo-3-(((tert-butyldimethylsilyl)oxy)-methyl)-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate 、 ethyl (1R,3S)-5-bromo-3-(((tert-butyldimethylsilyl)oxy)methyl)-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate
  参考文献：
  名称：

  Synthetic studies on lemonomycin: construction of the tetracyclic core

  摘要：

  A substrate-induced stereocontrol strategy was used to gain access to the tetracyclic core of (-)-lemonomycin. An advanced intermediate was prepared from a known substituted tyrosinol through a 16-step sequence, which involved a Pictet-Spengler reaction, a [3+2] dipolar cycloaddition and an enamide hydrogenation. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.05.009

文献信息

• Synthetic studies on lemonomycin: construction of the tetracyclic core
  作者：Alberto Jiménez-Somarribas、Robert M. Williams

  DOI：10.1016/j.tet.2013.05.009

  日期：2013.9

  A substrate-induced stereocontrol strategy was used to gain access to the tetracyclic core of (-)-lemonomycin. An advanced intermediate was prepared from a known substituted tyrosinol through a 16-step sequence, which involved a Pictet-Spengler reaction, a [3+2] dipolar cycloaddition and an enamide hydrogenation. (C) 2013 Published by Elsevier Ltd.