ethyl 5-(2-bromo-3-formyl-6-methoxyphenoxy)-3,4,5,6,7,8-hexahydro-1H-isoquinoline-2-carboxylate | 263406-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 5-(2-bromo-3-formyl-6-methoxyphenoxy)-3,4,5,6,7,8-hexahydro-1H-isoquinoline-2-carboxylate
• CAS: 263406-16-2
• 化学式: C₂₀H₂₄BrNO₅
• 分子量: 438.318
• InChiKey: AATNUTOHNJVGLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5-(2-bromo-3-formyl-6-methoxyphenoxy)-3,4,5,6,7,8-hexahydro-1H-isoquinoline-2-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以88%的产率得到5-(2-Bromo-3-hydroxymethyl-6-methoxy-phenoxy)-3,4,5,6,7,8-hexahydro-1H-isoquinoline-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Total synthesis of (±)-desoxycodeine-d: a novel route to the morphine skeleton

  摘要：

  A novel approach towards the construction of the morphine skeleton was demonstrated by a total synthesis of (+/-)-desoxycodeine-D (11) from 5,6,7,8-tetrahydroisoquinoline and isovanillin. The key steps are two consecutive Pd-catalyzed cyclizations and a Stevens rearrangement for the formation of ring B. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02188-7
• 作为产物：
  描述：

  2-溴-3-羟基-4-甲氧基苯甲醛 、 ethyl 5-hydroxy-3,4,5,6,7,8-hexahydro-1H-isoquinoline-2-carboxylate 在 三丁基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到ethyl 5-(2-bromo-3-formyl-6-methoxyphenoxy)-3,4,5,6,7,8-hexahydro-1H-isoquinoline-2-carboxylate
  参考文献：
  名称：

  Total synthesis of (±)-desoxycodeine-d: a novel route to the morphine skeleton

  摘要：

  A novel approach towards the construction of the morphine skeleton was demonstrated by a total synthesis of (+/-)-desoxycodeine-D (11) from 5,6,7,8-tetrahydroisoquinoline and isovanillin. The key steps are two consecutive Pd-catalyzed cyclizations and a Stevens rearrangement for the formation of ring B. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02188-7

文献信息

• Total synthesis of (±)-desoxycodeine-d: a novel route to the morphine skeleton
  作者：Jing-Ping Liou、Chen-Yu Cheng

  DOI：10.1016/s0040-4039(99)02188-7

  日期：2000.2

  A novel approach towards the construction of the morphine skeleton was demonstrated by a total synthesis of (+/-)-desoxycodeine-D (11) from 5,6,7,8-tetrahydroisoquinoline and isovanillin. The key steps are two consecutive Pd-catalyzed cyclizations and a Stevens rearrangement for the formation of ring B. (C) 2000 Elsevier Science Ltd. All rights reserved.