(1R-trans)-1,2,3,4-tetrahydro-1,3-dimethyl-6,8-bis(phenylmethoxy)-2-phenylmethylisoquinoline | 160539-02-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (1R-trans)-1,2,3,4-tetrahydro-1,3-dimethyl-6,8-bis(phenylmethoxy)-2-phenylmethylisoquinoline
• 英文别名: (1R,3R)-N-Benzyl-6,8-bis(benzyloxy)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline；(1R,3R)-2-benzyl-6,8-dibenzyloxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline；(1R,3R)-2-benzyl-1,3-dimethyl-6,8-bis(phenylmethoxy)-3,4-dihydro-1H-isoquinoline
• CAS: 160539-02-6
• 化学式: C₃₂H₃₃NO₂
• 分子量: 463.62
• InChiKey: QVOFLENDBBJIHW-JWQCQUIFSA-N

物化性质

• 沸点：
  599.3±50.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R-trans)-1,2,3,4-tetrahydro-1,3-dimethyl-6,8-bis(phenylmethoxy)-2-phenylmethylisoquinoline 在 溴 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (1R-trans)-5-bromo-1,2,3,4-tetrahydro-1,3-dimethyl-6,8-bis(phenylmethoxy)-2-(phenylmethyl)isoquinoline
  参考文献：
  名称：

  Bringmann, Gerhard; Goetz, Roland; Harmsen, Sven, Liebigs Annalen, 1996, # 12, p. 2045 - 2058

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R,3R)-2-benzyl-6,8-dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline 在 氢溴酸 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (1R-trans)-1,2,3,4-tetrahydro-1,3-dimethyl-6,8-bis(phenylmethoxy)-2-phenylmethylisoquinoline
  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

• The synthesis and biological activity of two analogs of the anti-HIV alkaloid michellamine B
  作者：Velaparthi Upender、Daniel J. Pollart、Jyanwei Liu、Peter D. Hobbs、Cris Olsen、Wan-Ru Chao、Bonnie Bowden、Jac L. Crase、David W. Thomas、Anjali Pandey、John A. Lawson、Marcia I. Dawson

  DOI：10.1002/jhet.5570330460

  日期：1996.7

  respectively. These analogs inhibited recombinant HIV reverse transcriptase with IC5() values of 62 μM and 1000 μM, respectively, whereas the IC5() value for michellamine B was 33 μM. Both michellamine B and the analogs inhibited the phosphorylation of histories by rat brain protein kinase C. The analogs were more active (IC50 values of 36 μM and 30 μM, respectively) than michellamine B (IC50 = 130 μM)

  二聚萘基四氢异喹啉生物碱米切胺B [4'，4“ -didesmethoxy-2'，2” -didesmethylmichellamine B和6,8-dihydroxy-5-（1'，1“ -dihydroxy-2'，2”的两个简化类似物-Suzuki钯催化的4-（2-苄基-6,8-二苄氧基-）的联芳基偶联反应合成了[ -binaphthalen-4'-yl）-1 R，3 R-二甲基-1,2,3,4-四氢异喹啉] 1 R，3 R-二甲基-1,2,3,4-四氢异喹啉-5-基）-1-苄氧基-2-溴萘分别转化为其相应的阻转异构体2-萘硼酸和1-苄氧基-2-萘硼酸。这些类似物抑制重组HIV逆转录酶与IC 5（）的62μ值中号和1000μ中号分别，而IC 5（）为michellamine B值为33μ中号。既michellamine B和类似物抑制历史的磷酸化的大鼠脑蛋白激酶C的类似物是多种活性（IC
• 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.
• Total synthesis of Michellamines A-C: Important anti-HIV agents
  作者：Thomas R. Hoye、Minzhang Chen、Liang Mi、Owen P. Priest

  DOI：10.1016/s0040-4039(00)78487-5

  日期：1994.11

  Michellamines A-C have been prepared by total synthesis in 7 and 16 linear steps from known and commercial materials, respectively. Key steps include i) palladium(0)-mediated biaryl coupling, ii) silver oxide promoted oxidative 1-naphthol coupling to an atropisomeric mixture of cross-ring quinones (indigoids), and iii) simultaneous per-debenzylation/reductive bleaching to the central 2,2'-binaphthol.
• First Total Synthesis of Korupensamines A and B
  作者：Gerhard Bringmann、Roland Götz、Paul A. Keller、Rainer Walter、Petra Henschel、Manuela Schäffer、Michaela Stäblein、T. Ross Kelly、Michael R. Boyd

  DOI：10.3987/com-94-s(b)79

  日期：——

  The first total synthesis of korupensamines A (1a) and B (1b), highly polar naphthylisoquinoline alkaloids and, simultaneously, 'monomeric building blocks' of the michellamines, is described. Key step is the Pd-II catalyzed intermolecular biaryl coupling of the two appropriately protected naphthalene and isoquinoline moieties (10) and (11), with the coupling positions activated by bromine and trialkylstannane substituents respectively.