7-benzyloxy-1,2,3,4-tetrahydro-6-methoxy-1-(3',4'-methylenedioxy)-benzyl-N-trifluoroacetylisoquinoline | 152035-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 7-benzyloxy-1,2,3,4-tetrahydro-6-methoxy-1-(3',4'-methylenedioxy)-benzyl-N-trifluoroacetylisoquinoline
• CAS: 152035-14-8
• 化学式: C₂₇H₂₄F₃NO₅
• 分子量: 499.486
• InChiKey: WZJRIDROJHDMNR-UHFFFAOYSA-N

物化性质

• 沸点：
  639.0±55.0 °C(predicted)
• 密度：
  1.338±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.23
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  7-benzyloxy-1,2,3,4-tetrahydro-6-methoxy-1-(3',4'-methylenedioxy)-benzyl-N-trifluoroacetylisoquinoline 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以89.6%的产率得到(+/-)-1-piperonyltetrahydroisoquinolin-7-ol
  参考文献：
  名称：

  Formation and Reaction of p-Quinol Acetates of N-Trifluoroacetyltetrahydroisoqunolin-7-ols

  摘要：

  Lead tetraacetate oxidation of N-trifluoroacetyltetrahydroisoquinolin-7-ols (13a, b) in AcOH gave stable p-quinol acetates (17a, b). Reaction of 17 with trifluoroacetic acid in CH2Cl2 or MeCN gave morphinandienones (15) and aporphines (16), respectively. In contrast with o-quinol acetates (14), it was found that reaction of p-quinol acetates (17) in MeCN was considerably slower than that in CH2Cl2. A mechanistic pathway on the reaction is deduced.

  DOI：

  10.3987/com-92-s(t)95
• 作为产物：
  描述：

  1-benzo[1,3]dioxol-5-ylmethyl-7-benzyloxy-6-methoxy-3,4-dihydro-isoquinoline; hydrochloride 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 7-benzyloxy-1,2,3,4-tetrahydro-6-methoxy-1-(3',4'-methylenedioxy)-benzyl-N-trifluoroacetylisoquinoline
  参考文献：
  名称：

  Formation and Reaction of p-Quinol Acetates of N-Trifluoroacetyltetrahydroisoqunolin-7-ols

  摘要：

  Lead tetraacetate oxidation of N-trifluoroacetyltetrahydroisoquinolin-7-ols (13a, b) in AcOH gave stable p-quinol acetates (17a, b). Reaction of 17 with trifluoroacetic acid in CH2Cl2 or MeCN gave morphinandienones (15) and aporphines (16), respectively. In contrast with o-quinol acetates (14), it was found that reaction of p-quinol acetates (17) in MeCN was considerably slower than that in CH2Cl2. A mechanistic pathway on the reaction is deduced.

  DOI：

  10.3987/com-92-s(t)95