1-甲氧羰基-6,7-二甲氧基-1,2,3,4-四氢异喹啉 | 263570-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: 1-甲氧羰基-6,7-二甲氧基-1,2,3,4-四氢异喹啉
• 英文名称: methyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-acetate
• 英文别名: (6,7-dimethoxy-1,2,3,4-tetrahydro-[1]isoquinolyl)-acetic acid methyl ester；(6,7-Dimethoxy-1,2,3,4-tetrahydro-[1]isochinolyl)-essigsaeure-methylester；Methyl 2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate
• CAS: 263570-28-1
• 化学式: C₁₄H₁₉NO₄
• mdl: MFCD00197593
• 分子量: 265.309
• InChiKey: NVXHORURRXLOGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  377.7±42.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)
• 溶解度：
  >39.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  1-甲氧羰基-6,7-二甲氧基-1,2,3,4-四氢异喹啉 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三氧化硫吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 27.0h， 生成 tert-butyl-6,7-dimethoxy-1-(2-oxoethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
  参考文献：
  名称：

  Synthesis of Bridged Benzoazabicyclic Compounds Using Radical Translocation/Cyclization Reactions of 1-Alkynyl-2-(o-iodobenzoyl)tetrahydroisoquinolines

  摘要：

  Bu3SnH-mediated radical translocation/cyclization reactions of 1-alkynyl-2-(o-iodobenzoyl)tetrahydroisoquinolines were examined. The 1-[3-(trimethylsilyl)prop-2-ynyl]- (10a) and 1-[4-(trimethylsilyl)but-3-ynyl]-1,2,3,4-tetrahydroisoquinoline derivatives (10b), with Bu3SnH in the presence of azobis(isobutyronitrile) in boiling toluene, gave regioselectively the 6,7,8,9-tetrahydro-5H-benzocyclohepten-5,8-imine (12a) and 5,6,7,8,9,10-hexahydrobenzocycloocten-5,9-imine (12b), respectively.

  DOI：

  10.3987/com-99-s91
• 作为产物：
  描述：

  methyl 3-{[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]amino}prop-2-enoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 3.0h， 以82%的产率得到1-甲氧羰基-6,7-二甲氧基-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  A Study of Aryl Radical Cyclization in Enaminone Esters

  摘要：

  Aryl radical cyclization in N-phenyl, N-benzyl, and N-phenethyl enaminone esters 1a-f was studied. N-Benzyl and N-phenethyl enaminones afforded 5-exo and 6-exo cyclization products, respectively, but radical cyclization did not occur in N-phenyl enaminones. The rate constants for the 5-exo and 6-exo cyclization processes in secondary enaminones were estimated as being on the order of 107 s(-1) at 353 K; since DNMR experiments showed the rate constant for rotation around the enaminone C3-N bond to be on the order of 10(4) s(-1) at this temperature, the initial enaminone configuration is maintained throughout the cyclization process. PM3 calculations suggested that the nonoccurrence of endo and 4-exo cyclizations is due to the corresponding transition structures involving significant distortion of the conjugated enaminone system.

  DOI：

  10.1021/jo0107857

文献信息

• A Study of Aryl Radical Cyclization in Enaminone Esters
  作者：Armando Navarro-Vázquez、Alberto García、Domingo Domínguez

  DOI：10.1021/jo0107857

  日期：2002.5.1

  Aryl radical cyclization in N-phenyl, N-benzyl, and N-phenethyl enaminone esters 1a-f was studied. N-Benzyl and N-phenethyl enaminones afforded 5-exo and 6-exo cyclization products, respectively, but radical cyclization did not occur in N-phenyl enaminones. The rate constants for the 5-exo and 6-exo cyclization processes in secondary enaminones were estimated as being on the order of 107 s(-1) at 353 K; since DNMR experiments showed the rate constant for rotation around the enaminone C3-N bond to be on the order of 10(4) s(-1) at this temperature, the initial enaminone configuration is maintained throughout the cyclization process. PM3 calculations suggested that the nonoccurrence of endo and 4-exo cyclizations is due to the corresponding transition structures involving significant distortion of the conjugated enaminone system.
• Synthesis of Bridged Benzoazabicyclic Compounds Using Radical Translocation/Cyclization Reactions of 1-Alkynyl-2-(o-iodobenzoyl)tetrahydroisoquinolines
  作者：Masazumi Ikeda、Masahiro Hamada、Serry A. A. El Bialy、Katsuaki Matsui、Shimpei Kawakami、Yuka Nakano、Said M. M. Bayomi、Tatsunori Sato

  DOI：10.3987/com-99-s91

  日期：——

  Bu3SnH-mediated radical translocation/cyclization reactions of 1-alkynyl-2-(o-iodobenzoyl)tetrahydroisoquinolines were examined. The 1-[3-(trimethylsilyl)prop-2-ynyl]- (10a) and 1-[4-(trimethylsilyl)but-3-ynyl]-1,2,3,4-tetrahydroisoquinoline derivatives (10b), with Bu3SnH in the presence of azobis(isobutyronitrile) in boiling toluene, gave regioselectively the 6,7,8,9-tetrahydro-5H-benzocyclohepten-5,8-imine (12a) and 5,6,7,8,9,10-hexahydrobenzocycloocten-5,9-imine (12b), respectively.