(1R,3R)-(-)-6,8-dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinoline | 160538-95-4

• 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: (1R,3R)-(-)-6,8-dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinoline
• 英文别名: (1R, 3R)-1,2,3,4-tetrahydro-6,8-dimethoxy-1,3-dimethyl-isoquinoline；(1R,3R)-6,8-dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline
• CAS: 160538-95-4
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: VRGRFDNHLOPXIW-RKDXNWHRSA-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：

  (1R,3R)-(-)-6,8-dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinoline 在 四(三苯基膦)钯 碘 、 三溴化硼 、 碳酸氢钠 、 caesium carbonate 、 silver sulfate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 生成 5-[(R(a),1R,3R)-2-phenylmethyl-6,8-bis-phenylmethoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-1-methoxy-8-methoxymethoxy-3-methylnaphthalene
  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 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

文献信息

• 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。
• 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
• Method and intermediates for the synthesis of korupensamines
  申请人：Regents of the University of Minnesota

  公开号：US05543523A1

  公开（公告）日：1996-08-06

  Activated isoquinolines and naphthalenes are disclosed which are useful to prepare korupensamines, michellamines and analogs thereof.

  已公开激活的异喹啉和萘烯，可用于制备科鲁佩南胺、米切拉胺及其类似物。
• Enantioselective Synthesis of β-Arylamines via Chiral Phosphoric Acid-Catalyzed Asymmetric Reductive Amination
  作者：Kyung-Hee Kim、Chun-Young Lee、Cheol-Hong Cheon

  DOI：10.1021/acs.joc.5b00812

  日期：2015.6.19

  A new method for the synthesis of chiral β-aryl amines via chiral phosphoric acid-catalyzed enantioselective reductive amination of benzyl methyl ketone derivatives with Hantzsch ester was developed. Various chiral β-aryl amines were obtained in high yields and with good to high enantioselectivities. This transformation is applicable to gram-scale reactions, and the catalyst loading can be reduced

  开发了一种新的手性β-芳基胺的合成方法，该方法是通过手性磷酸催化的汉茨基酯对甲基苄基酮衍生物进行对映选择性还原胺化。以高收率和良好至高对映选择性获得了各种手性β-芳基胺。该转化适用于克级反应，并且催化剂的负载量可以降低至1mol％而不会牺牲任何催化效率。此外，将所得的β-芳基胺成功地转化为四氢异喹啉化合物，而没有任何对映选择性的损失。
• Asymmetric synthesis of alkaloids using polyfunctionalized chiral building blocks
  作者：Franklin A. Davis、Bin Chao、Yemane W. Andemichael、Pradyumna K. Mohanty、Tianan Fang、David M. Burns、Ashwin Rao、Joanna M. Szewczyk

  DOI：10.1002/hc.10090

  日期：——

  Enantiopure N-sulfinyl-δ-amino-β-ketoesters and isoquinolones, prepared from sulfinimines (N-sulfinyl imines) are a new class of polyfunctionalized chiral building blocks. These building blocks provide easy access to enantiomerically pure, functionalized piperidines and tetrahydroisoquinolines with a minimum of chemical manipulation and protecting-group chemistry. © 2002 Wiley Periodicals, Inc. Heteroatom

  由亚磺亚胺（N-亚磺酰基亚胺）制备的对映体纯 N-亚磺酰基-δ-氨基-β-酮酯和异喹诺酮类是一类新的多官能化手性结构单元。这些结构单元可轻松获得对映异构纯的官能化哌啶和四氢异喹啉，且化学操作和保护基团化学最少。© 2002 Wiley Periodicals, Inc. 杂原子化学 13:486–492, 2002; 在线发表于 Wiley Interscience (www.interscience.wiley.com)。DOI 10.1002/hc.10090