(1S-trans)-1,2,3,4-tetrahydro-8-methoxy-1,3-dimethyl-6-isoquinolinol | 135531-84-9

• 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: (1S-trans)-1,2,3,4-tetrahydro-8-methoxy-1,3-dimethyl-6-isoquinolinol
• 英文别名: (1S,3S)-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-ol
• CAS: 135531-84-9
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: RNCDEHUVRUVRIQ-YUMQZZPRSA-N

物化性质

• 沸点：
  360.7±42.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S-trans)-1,2,3,4-tetrahydro-8-methoxy-1,3-dimethyl-6-isoquinolinol 在 ruthenium trichloride sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 (S)-3-氨基丁酸
  参考文献：
  名称：

  A facile degradation procedure for determination of absolute configuration in 1,3-dimethyltetra- and dihydroisoquinolines

  摘要：

  The ruthenium-mediated oxidative degradation of chiral 1,3-dimethyl substituted di- and tetrahydroisoquinolines is described. Preparative isolation of the resulting 3-aminobutyric acid, or its analysis by GC after Moshertype derivatization, gives direct information on the configuration at C-3 of the tetrahydroisoquinoline. For trans-configurated tetrahydroisoquinolines, the stereocentre at C-1 may also be elucidated in the same analytical step, by analysis of the amino acid alanine formed. The applicability of the method to the analysis of natural products is demonstrated for naphthylisoquinoline alkaloids.

  DOI：

  10.1016/0031-9422(91)85068-b
• 作为产物：
  描述：

  trans-6,8-Dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 以43%的产率得到(1S-trans)-1,2,3,4-tetrahydro-8-methoxy-1,3-dimethyl-6-isoquinolinol
  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

文献信息

• Total syntheses of korupensamine C and ancistrobrevine B
  作者：Thomas R Hoye、Liang Mi

  DOI：10.1016/0040-4039(96)00525-4

  日期：1996.4

  The first total syntheses of korupensamine C (3) and ancistrobrevine B (4) have been achieved. Important benzyne chemistry related to the construction of the naphthalene moiety, manipulation of methoxy groups on the tetrahydroisoquinoline unit, and hindered biaryl formation are described.

  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。
• 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.
• A facile degradation procedure for determination of absolute configuration in 1,3-dimethyltetra- and dihydroisoquinolines
  作者：Gerhard Bringmann、Torsten Geuder、Martin Rübenacker、Rainer Zagst

  DOI：10.1016/0031-9422(91)85068-b

  日期：1991.1

  The ruthenium-mediated oxidative degradation of chiral 1,3-dimethyl substituted di- and tetrahydroisoquinolines is described. Preparative isolation of the resulting 3-aminobutyric acid, or its analysis by GC after Moshertype derivatization, gives direct information on the configuration at C-3 of the tetrahydroisoquinoline. For trans-configurated tetrahydroisoquinolines, the stereocentre at C-1 may also be elucidated in the same analytical step, by analysis of the amino acid alanine formed. The applicability of the method to the analysis of natural products is demonstrated for naphthylisoquinoline alkaloids.