(1S,2S)-methyl-(2-pyrrolidin-1-yl-1,2,3,4-tetrahydro-naphthalen-1-yl)-amin | 475495-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1S,2S)-methyl-(2-pyrrolidin-1-yl-1,2,3,4-tetrahydro-naphthalen-1-yl)-amin
• 英文别名: trans-1,2,3,4-tetrahydro-1-methylamino-2-(pyrrolidin-1-yl)naphthalene；(1S,2S)-N-methyl-2-pyrrolidin-1-yl-1,2,3,4-tetrahydronaphthalen-1-amine
• CAS: 475495-77-3
• 化学式: C₁₅H₂₂N₂
• 分子量: 230.353
• InChiKey: BLAFSMXCRFQMMZ-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-二氯苯乙酸 、 (1S,2S)-methyl-(2-pyrrolidin-1-yl-1,2,3,4-tetrahydro-naphthalen-1-yl)-amin 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以90%的产率得到(1S,2S)-2-(3,4-dichloro-phenyl)-N-methyl-N-(2-pyrrolidin-1-yl-1,2,3,4-tetrahydronaphthalen-1-yl)-acetamide
  参考文献：
  名称：

  An Expedient Enantioselective Route to Diaminotetralins:  Application in the Preparation of Analgesic Compounds

  摘要：

  [GRAPHICS]Advances to the rhodium-catalyzed asymmetric ring-opening protocol have allowed this methodology to be extended to azabicyclic alkenes, the first time that rhodium has been used in allylic functionalizations with nitrogen leaving groups. The product diaminotetralins are important medicinal compounds. The synthetic utility of this methodology has been demonstrated in the total synthesis of an analgesic compound where the tetralin core, the regiochemistry, and the relative and absolute stereochemistry are all established in the ring-opening step.

  DOI：

  10.1021/ol026579i
• 作为产物：
  描述：

  (1S,2S)-methyl-(2-pyrrolidin-1-yl-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以95%的产率得到(1S,2S)-methyl-(2-pyrrolidin-1-yl-1,2,3,4-tetrahydro-naphthalen-1-yl)-amin
  参考文献：
  名称：

  An Expedient Enantioselective Route to Diaminotetralins:  Application in the Preparation of Analgesic Compounds

  摘要：

  [GRAPHICS]Advances to the rhodium-catalyzed asymmetric ring-opening protocol have allowed this methodology to be extended to azabicyclic alkenes, the first time that rhodium has been used in allylic functionalizations with nitrogen leaving groups. The product diaminotetralins are important medicinal compounds. The synthetic utility of this methodology has been demonstrated in the total synthesis of an analgesic compound where the tetralin core, the regiochemistry, and the relative and absolute stereochemistry are all established in the ring-opening step.

  DOI：

  10.1021/ol026579i

文献信息

• Benoz-fused cycloalkane trans-1,2-diamine derivatives
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04876269A1

  公开（公告）日：1989-10-24

  Benzo-fused cycloalkane and oxa- and thia-cycloalkane trans-1,2-diamine compounds of the formula: ##STR1## wherein A, B, C, D, n, X, Y, R, R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification, e.g., trans-3,4-dichloro-N-methyl-N-[2-(pyrrolidin-1-yl)-5-methoxy-1,2,3,4-tetra hydronaphth-1-yl]benzeneacetamide, and the pharmaceutically acceptable salts of N-oxides thereof, are useful as analgesics and/or diuretics.

  苯并环戊烷和氧杂环戊烷和硫杂环戊烷的trans-1,2-二胺化合物的化学式为：##STR1## 其中A、B、C、D、n、X、Y、R、R.sup.1、R.sup.2和R.sup.3如规范中定义，例如，trans-3,4-二氯-N-甲基-N-[2-(吡咯烷-1-基)-5-甲氧基-1,2,3,4-四氢萘-1-基]苯乙酰胺，以及其N-氧化物的药用可接受的盐，可用作镇痛剂和/或利尿剂。
• Benzo-fused cycloalkane and oxa- and thia-, cycloalkane trans-1,2-diamine derivatives
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0260555B1

  公开（公告）日：1992-04-22
• US4876269A
  申请人：——

  公开号：US4876269A

  公开（公告）日：1989-10-24
• US4929627A
  申请人：——

  公开号：US4929627A

  公开（公告）日：1990-05-29
• US5010085A
  申请人：——

  公开号：US5010085A

  公开（公告）日：1991-04-23