(1S,3R)-(-)-6,8-dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroiso-quinoline | 178150-77-1

• 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,3R)-(-)-6,8-dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroiso-quinoline
• 英文别名: (1S-cis)-1,2,3,4-tetrahydro-6,8-dimethoxy-1,3-dimethylsoquinoline；(1S,3R)-6,8-dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline
• CAS: 178150-77-1
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: VRGRFDNHLOPXIW-BDAKNGLRSA-N

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：

  (1S,3R)-(-)-6,8-dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroiso-quinoline 在 四丁基氟化铵 、 三溴化硼 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (1S-cis)-N-carbethoxy-1,2,3,4-tetrahydro-1,3-dimethyl-6,8-isoquinolinediol
  参考文献：
  名称：

  （ent）-甲氨苯丁胺D的全合成

  摘要：

  描述了天然产物对映异构体D（16R）的对映异构体的第一次全合成。关键步骤包括通过氮丙啶2与芳基铜酸酯试剂的开环高效制备对映体纯的伯胺4以及在酚羟基存在的情况下开发受阻仲胺的一锅选择性功能化，8至9）。

  DOI：

  10.1016/0040-4039(96)00524-2
• 作为产物：
  描述：

  2, 4-二甲氧基-6-甲基苯甲腈 在 sodium tetrahydroborate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二乙二醇二甲醚 为溶剂， 反应 16.75h， 生成 (1S,3R)-(-)-6,8-dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroiso-quinoline
  参考文献：
  名称：

  磺胺类药物介导的1,3-二取代四氢异喹啉的不对称合成：顺式和反式6,8-二甲氧基-1,3-二甲基-1,2,3,4-四氢异喹啉的立体选择性合成。

  摘要：

  [反应：见正文]在亚磺胺中高度非对映选择性地将侧基锂化邻甲苯二酚加成，然后用MeLi处理所得的亚磺酰胺，进行水解和还原反应，代表了一种简洁的新方法，用于不对称合成1,3-二取代的四氢异喹啉。

  DOI：

  10.1021/ol006654u

文献信息

• Total synthesis of (ent)-korupensamine D
  作者：Thomas R. Hoye、Minzhang Chen

  DOI：10.1016/0040-4039(96)00524-2

  日期：1996.4

  enantiomer of the natural product, korupensamine D (16R), is described. The key steps include a highly efficient preparation of the enantiomerically pure primary amine 4 via the ring opening of aziridine 2 with an arylcuprate reagent and the development of a one-pot selective functionalization of a hindered secondary amine in the presence of phenolic hydroxyl groups (i.e., 8 to 9).

  描述了天然产物对映异构体D（16R）的对映异构体的第一次全合成。关键步骤包括通过氮丙啶2与芳基铜酸酯试剂的开环高效制备对映体纯的伯胺4以及在酚羟基存在的情况下开发受阻仲胺的一锅选择性功能化，8至9）。
• Sulfinimine-Mediated Asymmetric Synthesis of 1,3-Disubstituted Tetrahydroisoquinolines:  A Stereoselective Synthesis of <i>cis</i>- and <i>trans</i>-6,8-Dimethoxy-1,3-dimethyl- 1,2,3,4-tetrahydroisoquinoline
  作者：Franklin A. Davis、Pradyumna K. Mohanty、David M. Burns、Yemane W. Andemichael

  DOI：10.1021/ol006654u

  日期：2000.11.1

  lithiated o-tolunitriles to sulfinimines followed by treatment of the resulting sulfinamide with MeLi, hydrolysis, and reduction represents a concise new methodology for the asymmetric synthesis of 1,3-disubstituted tetrahydroisoquinolines.

  [反应：见正文]在亚磺胺中高度非对映选择性地将侧基锂化邻甲苯二酚加成，然后用MeLi处理所得的亚磺酰胺，进行水解和还原反应，代表了一种简洁的新方法，用于不对称合成1,3-二取代的四氢异喹啉。
• 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.