(R,R)-N-<1-(3,5-dimethoxyphenyl)-2-propyl>-α-methylbenzenemethanamine | 250212-49-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R,R)-N-<1-(3,5-dimethoxyphenyl)-2-propyl>-α-methylbenzenemethanamine
• 英文别名: (2R)-1-(3,5-dimethoxyphenyl)-N-[(1R)-1-phenylethyl]propan-2-amine
• CAS: 250212-49-8
• 化学式: C₁₉H₂₅NO₂
• 分子量: 299.413
• InChiKey: SYEUWNAKPZKYGI-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  (R,R)-N-<1-(3,5-dimethoxyphenyl)-2-propyl>-α-methylbenzenemethanamine 在 钯 lithium aluminium tetrahydride 、 三甲基铝 、 甲酸铵 、 三乙胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (1R,3R)-(-)-6,8-dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinoline
  参考文献：
  名称：

  Total synthesis of Michellamines A-C: Important anti-HIV agents

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)78487-5
• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 在 Ra-Ni ammonium acetate 、 氢气 、 铁粉 、 溶剂黄146 作用下， 以 乙醇 、 甲苯 为溶剂， 100.0~110.0 ℃ 、344.73 kPa 条件下， 反应 81.0h， 生成 (R,R)-N-<1-(3,5-dimethoxyphenyl)-2-propyl>-α-methylbenzenemethanamine
  参考文献：
  名称：

  两种抗HIV生物碱Michellamine B的合成及其生物学活性

  摘要：

  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

  DOI：

  10.1002/jhet.5570330460

文献信息

• 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.