(1R)-2-(3,5-dimethoxyphenyl)-1-methylethylamine | 177971-34-5

• 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: (1R)-2-(3,5-dimethoxyphenyl)-1-methylethylamine
• 英文别名: (2R)-1-(3',5'-dimethoxyphenyl)-2-aminopropane；(2R)-1-(3,5-dimethoxyphenyl)propan-2-amine
• CAS: 177971-34-5
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: PDCLPGSYMZLLDX-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R)-2-(3,5-dimethoxyphenyl)-1-methylethylamine 在 lithium aluminium tetrahydride 、 三甲基铝 、 三乙胺 、 三氯氧磷 作用下， 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：

  (R,R)-N-<1-(3,5-dimethoxyphenyl)-2-propyl>-α-methylbenzenemethanamine 在 钯 甲酸铵 作用下， 以 乙醇 为溶剂， 生成 (1R)-2-(3,5-dimethoxyphenyl)-1-methylethylamine
  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

文献信息

• Total Synthesis of the <i>N</i>,<i>C</i>-Coupled Naphthylisoquinoline Alkaloids Ancistrocladinium A and B and Related Analogues
  作者：Gerhard Bringmann、Tanja Gulder、Barbara Hertlein、Yasmin Hemberger、Frank Meyer

  DOI：10.1021/ja9097687

  日期：2010.1.27

  activities, have been synthesized via a short sequence of eight linear steps, without the need of protecting groups. Key steps were a Buchwald-Hartwig amination and a Bischler-Napieralski cyclization, preferentially leading to the naturally predominant M-atropo-diastereomer in the case of 3, while the N,C-axis is configurationally semistable in 4. The highly convergent first access to this type of alkaloids

  N,C-偶联萘基二氢异喹啉生物碱 ancistrocladinium A (3) 和 B (4) 具有前所未有的亚胺-芳基轴并显示出高体外抗利什曼病活性，已通过八个线性步骤的短序列合成，无需保护组。关键步骤是 Buchwald-Hartwig 胺化和 Bischler-Napieralski 环化，在 3 的情况下优先导致自然占优势的 M-atropo-非对映异构体，而 N,C 轴在 4 中是构型半稳定的。 高度收敛的第一次访问这种类型的生物碱现在将有助于制备用于构效关系研究的结构类似物。它的普遍适用性通过制备空间上更加拥挤的、目前尚不自然的 N,3'-和 N,1'-偶联类似物来证明，
• 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）。
• Directed Synthesis of All Four Pure Stereoisomers of the <i>N</i>,<i>C</i>-Coupled Naphthylisoquinoline Alkaloid Ancistrocladinium A
  作者：Raina Seupel、Barbara Hertlein-Amslinger、Tanja Gulder、Philipp Stawski、Marcel Kaiser、Reto Brun、Gerhard Bringmann

  DOI：10.1021/acs.orglett.6b03480

  日期：2016.12.16

  The first preparation of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A and its likewise naturally occurring minor atropisomer, in an atropisomerically pure form, is described. The synthesis succeeded by resolution of the already rotationally hindered, and thus atropo-diastereomeric acetamide precursors, which were then, without major loss of stereochemical information, cyclized

  描述了N，C-偶联的萘基异喹啉碱生物碱Atrotrocladinium A及其类似天然存在的次要阻转异构体的第一制备，其形式为阻转异构体纯形式。合成通过拆分已经旋转受阻的阻转非对映异构的乙酰胺前体而成功，然后将其在没有重大立体化学信息损失的情况下环化成相应的靶分子。该策略同样以立体化学纯的形式应用于区域异构产物顺反子草D的首次合成。
• 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.
• Bringmann, Gerhard; Jansen, Johannes R.; Rink, Heinz-Peter, Angewandte Chemie, 1986, vol. 98, # 10, p. 917 - 919
  作者：Bringmann, Gerhard、Jansen, Johannes R.、Rink, Heinz-Peter

  DOI：——

  日期：——