N-((1R,2R)-6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-methoxymethyl-4-methyl-benzenesulfonamide | 406174-96-7

• 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: N-((1R,2R)-6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-methoxymethyl-4-methyl-benzenesulfonamide
• 英文别名: N-[(1R,2R)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl]-N-(methoxymethyl)-4-methylbenzenesulfonamide
• CAS: 406174-96-7
• 化学式: C₂₇H₃₁NO₅S
• 分子量: 481.613
• InChiKey: BPFAEUCCYQNPJR-SHQCIBLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-((1R,2R)-6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-methoxymethyl-4-methyl-benzenesulfonamide 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以94%的产率得到(6aR,12bS)-10,11-Dimethoxy-6-(toluene-4-sulfonyl)-5,6,6a,7,8,12b-hexahydro-benzo[a]phenanthridine
  参考文献：
  名称：

  The first asymmetric synthesis of a dopamine D1 agonist, dihydrexidine, employing asymmetric conjugate addition technology

  摘要：

  The first asymmetric synthesis of benzophenanthridine dopamine D1 full agonist, dihydrexidine, was accomplished employing three key processes, external chiral ligand-cont rolled conjugate addition of phenyllithium, Curtius conversion of a carboxylic group to an amino group, and finally Pictet-Spengler type cyclization completing skeleton construction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01823-8
• 作为产物：
  描述：

  (1R,2R)-6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester 在 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 N-((1R,2R)-6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-methoxymethyl-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  The first asymmetric synthesis of a dopamine D1 agonist, dihydrexidine, employing asymmetric conjugate addition technology

  摘要：

  The first asymmetric synthesis of benzophenanthridine dopamine D1 full agonist, dihydrexidine, was accomplished employing three key processes, external chiral ligand-cont rolled conjugate addition of phenyllithium, Curtius conversion of a carboxylic group to an amino group, and finally Pictet-Spengler type cyclization completing skeleton construction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01823-8

文献信息

• [EN] METHOD OF ADMINISTRATION OF DOPAMINE RECEPTOR AGONISTS<br/>[FR] PROCEDES D'ADMINISTRATION D'AGONISTES DU RECEPTEUR DE LA DOPAMINE
  申请人：DARPHARMA INC

  公开号：WO2006012640A3

  公开（公告）日：2009-04-16
• The first asymmetric synthesis of a dopamine D1 agonist, dihydrexidine, employing asymmetric conjugate addition technology
  作者：Yasutomi Asano、Mitsuaki Yamashita、Kazushige Nagai、Masami Kuriyama、Ken-ichi Yamada、Kiyoshi Tomioka

  DOI：10.1016/s0040-4039(01)01823-8

  日期：2001.11

  The first asymmetric synthesis of benzophenanthridine dopamine D1 full agonist, dihydrexidine, was accomplished employing three key processes, external chiral ligand-cont rolled conjugate addition of phenyllithium, Curtius conversion of a carboxylic group to an amino group, and finally Pictet-Spengler type cyclization completing skeleton construction. (C) 2001 Elsevier Science Ltd. All rights reserved.