trans-6,8-Dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline | 104292-10-6

• 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: trans-6,8-Dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: (1S,3S)-6,8-dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline
• CAS: 104292-10-6
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: VRGRFDNHLOPXIW-IUCAKERBSA-N

物化性质

• 沸点：
  336.6±42.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-6,8-Dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline 在 palladium on activated charcoal 四(三苯基膦)钯 、 正丁基锂 、 硼酸三甲酯 、 氨 、 氢溴酸 、 氢气 、 碘 、 碳酸氢钠 、 potassium carbonate 、 silver sulfate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 溶剂黄146 、 丁酮 为溶剂， 反应 4.0h， 生成 ancistrobrevine B
  参考文献：
  名称：

  甲胺苯丙胺C和顺牛膝B的总合成

  摘要：

  首次完成了科鲁苯胺C（3）和antrotrobrevine B（4）的首次合成。描述了与萘部分的构造，四氢异喹啉单元上甲氧基的操纵以及受阻联芳基的形成有关的重要的苯炔化学。

  DOI：

  10.1016/0040-4039(96)00525-4
• 作为产物：
  描述：

  (3,5-二甲氧基苯基)乙酮 在 palladium on activated charcoal 、 镍 lithium aluminium tetrahydride 、 氢气 、 三甲基铝 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 203.0h， 生成 trans-6,8-Dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Bringmann, Gerhard; Jansen, Johannes R.; Rink, Heinz-Peter, Angewandte Chemie, 1986, vol. 98, # 10, p. 917 - 919

  摘要：

  DOI：

文献信息

• Enantioselective Synthesis of β-Arylamines via Chiral Phosphoric Acid-Catalyzed Asymmetric Reductive Amination
  作者：Kyung-Hee Kim、Chun-Young Lee、Cheol-Hong Cheon

  DOI：10.1021/acs.joc.5b00812

  日期：2015.6.19

  A new method for the synthesis of chiral β-aryl amines via chiral phosphoric acid-catalyzed enantioselective reductive amination of benzyl methyl ketone derivatives with Hantzsch ester was developed. Various chiral β-aryl amines were obtained in high yields and with good to high enantioselectivities. This transformation is applicable to gram-scale reactions, and the catalyst loading can be reduced

  开发了一种新的手性β-芳基胺的合成方法，该方法是通过手性磷酸催化的汉茨基酯对甲基苄基酮衍生物进行对映选择性还原胺化。以高收率和良好至高对映选择性获得了各种手性β-芳基胺。该转化适用于克级反应，并且催化剂的负载量可以降低至1mol％而不会牺牲任何催化效率。此外，将所得的β-芳基胺成功地转化为四氢异喹啉化合物，而没有任何对映选择性的损失。
• Stereoselective Synthesis of<i>cis</i>-1,3-Dimethyltetrahydroisoquinolines: Formal Synthesis of Naphthylisoquinoline Alkaloids
  作者：Mercedes Amat、Fabiana Subrizi、Viviane Elias、Núria Llor、Elies Molins、Joan Bosch

  DOI：10.1002/ejoc.201200798

  日期：2012.10

  3-dimethyltetrahydroisoquinolines, synthetic precursors of naphthylisoquinoline alkaloids, has been developed. The synthesis relies on the use of a phenylglycinol-derived lactam as the starting enantiopure scaffold. After stereoselective opening of the oxazolidine ring, the C-3 methyl substituent was installed, taking advantage of the lactam carbonyl group by stereoselective hydrogenation of an α-methylenamide generated

  已开发出合成对映体纯 cis-1,3-二甲基四氢异喹啉（萘基异喹啉生物碱的合成前体）的合成路线。该合成依赖于使用苯基甘氨醇衍生的内酰胺作为起始对映体纯支架。在恶唑烷环立体选择性打开后，安装 C-3 甲基取代基，利用内酰胺羰基通过立体选择性氢化通过三氟甲磺酸乙烯酯生成的 α-亚甲基酰胺。
• Total Synthesis of Michellamines A−C, Korupensamines A−D, and Ancistrobrevine B
  作者：Thomas R. Hoye、Minzhang Chen、Bac Hoang、Liang Mi、Owen P. Priest

  DOI：10.1021/jo9908187

  日期：1999.9.1

  Efficient syntheses of the title compounds have been developed. Several strategies for preparation of each of the naphthalene and tetrahydroisoquinoline (THIQ) portions were developed. Initial attempts to use benzyne plus furan cycloaddition reactions were thwarted by the unfavorable sense of the regiochemical outcome. An interesting annulation reaction of benzynes derived from 2,4-dibromophenol derivatives formed the core of the shortest naphthalene synthesis. An alternative annulation initiated by the addition of a benzylic sulfone anion to methyl crotonate led to an efficient naphthol synthesis amenable to large scale. The THIQ synthesis of Bringmann was used initially and subsequently complemented by a route whose key step involved the opening of N-tosyl-2-methylethyleneimine by a 3,5-dimethoxyphenylcuprate reagent. The results from a variety of aryl cross-coupling reactions are described. Suzuki coupling of the boronic acid derived from the naphthalene moiety with a THIQ-iodide was the most generally effective method for forming the hindered biaryl bond. The korupensamines and ancistrobrevine B were then revealed by deprotection. The oxidative coupling of several 4-aryl-1-naphthols to indigoids (cross ring naphthoquinones) with silver oxide effected the critical dimerization reaction needed to establish the michellamine skeleton. For the perbenzylated precursor, hydrogen over palladium on carbon both reductively bleached the indigoid and hydrogenolyzed the benzyl ethers and amines to release the free michellamines. The synthesis of several michellamine analogues, including ent-michellamines, is outlined. Results of anti-HIV assays are presented.