(1R,2S)-N-methyl-2-(1-pyrrolidinyl)-1,2,3,4-tetrahydro-1-naphthalenamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1R,2S)-N-methyl-2-(1-pyrrolidinyl)-1,2,3,4-tetrahydro-1-naphthalenamine
• 英文别名: (1R,2S)-N-methyl-2-pyrrolidin-1-yl-1,2,3,4-tetrahydronaphthalen-1-amine
• 化学式: C₁₅H₂₂N₂
• 分子量: 230.353
• InChiKey: BLAFSMXCRFQMMZ-LSDHHAIUSA-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：

  3,4-二氯苯甲酰氯 、 (1R,2S)-N-methyl-2-(1-pyrrolidinyl)-1,2,3,4-tetrahydro-1-naphthalenamine 在 三乙胺 作用下， 以 乙醚 为溶剂， 以49%的产率得到
  参考文献：
  名称：

  Anticonvulsants related to U-54494 prepared from cis-1,2- and cis-2,3-diaminotetralin

  摘要：

  cis-Diaminotetralins 4 and 10 were converted in 4 steps to benzologs of the novel anticonvulsant U-54494. Attempted alkylation of 4 and 10 with 1,4-dibromobutane provided mixtures of the bis-pyrrolidino compounds and starting free bases together with the desired monopyrrolidino compounds 5 and 11. Treatment of these mixtures with ethyl chloroformate followed by chromatographic separation gave the carbamates 7 and 12. Reduction of these carbamates with LiAlH4 provided the N-methylamino compounds 8 and 14. Finally, benzamide formation gave rise to the analogs of U-54494, compounds 9 and 15.

  DOI：

  10.1016/s0040-4020(01)86548-0
• 作为产物：
  描述：

  ((1R,2S)-2-Pyrrolidin-1-yl-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到(1R,2S)-N-methyl-2-(1-pyrrolidinyl)-1,2,3,4-tetrahydro-1-naphthalenamine
  参考文献：
  名称：

  Anticonvulsants related to U-54494 prepared from cis-1,2- and cis-2,3-diaminotetralin

  摘要：

  cis-Diaminotetralins 4 and 10 were converted in 4 steps to benzologs of the novel anticonvulsant U-54494. Attempted alkylation of 4 and 10 with 1,4-dibromobutane provided mixtures of the bis-pyrrolidino compounds and starting free bases together with the desired monopyrrolidino compounds 5 and 11. Treatment of these mixtures with ethyl chloroformate followed by chromatographic separation gave the carbamates 7 and 12. Reduction of these carbamates with LiAlH4 provided the N-methylamino compounds 8 and 14. Finally, benzamide formation gave rise to the analogs of U-54494, compounds 9 and 15.

  DOI：

  10.1016/s0040-4020(01)86548-0

文献信息

• Novel compounds and a novel process for their preparation
  申请人：Fagnou Keith

  公开号：US20050014721A1

  公开（公告）日：2005-01-20

  The present invention is directed to a procedure for making an enantiomerically enriched compound containing a hydronaphthalene ring structure. The process involves reacting oxabenzonorbornadienes with nucleophiles using rhodium as a catalyst and in the presence of a phosphine ligand. The compounds synthesized may be used in pharmaceutical preparations for the treatment of a variety of diseases and conditions.

  本发明涉及一种制备含有氢化萘环结构的对映体富集化合物的方法。该过程涉及使用铑作为催化剂，并在膦配体的存在下，将氧化苯并[2,3-c]环辛二烯与亲核试剂反应。合成的化合物可用于制备治疗各种疾病和病况的药物制剂。
• Novel hydronaphthalene compounds, prepared by a rhodium catalysed ring opening reaction in the presence of phosphine ligand
  申请人：AstraZeneca AB

  公开号：EP1498406A1

  公开（公告）日：2005-01-19

  The present invention is directed to a procedure for making an enantiomerically enriched compound containing a hydronaphthalene ring structure. The process involves reacting oxabenzonorbornadienes with nucleophiles using rhodium as a catalyst and in the presence of a phosphine ligand. The compounds synthesized may be used in pharmaceutical preparations for the treatment of a variety of diseases and conditions.

  本发明涉及一种含有氢萘环结构的对映体富集化合物的制造工艺。该过程包括使用铑作为催化剂，在膦配体存在的情况下，使氧杂苯并降冰片二烯与亲核物反应。合成的化合物可用于治疗各种疾病和病症的药物制剂中。
• NOVEL HYDRONAPHTHALENE COMPOUNDS, PREPARED BY A RHODIUM CATALYZED RING OPENING REACTION IN THE PRESENCE OF PHOSPHINE LIGAND
  申请人：AstraZeneca AB

  公开号：EP1228024B1

  公开（公告）日：2004-09-01
• US6525068B1
  申请人：——

  公开号：US6525068B1

  公开（公告）日：2003-02-25
• US6784210B2
  申请人：——

  公开号：US6784210B2

  公开（公告）日：2004-08-31