(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

• 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: (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride
• 英文别名: 1(S)-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride；(1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline;hydrochloride
• 化学式: C₁₅H₁₅N*ClH
• 分子量: 245.752
• InChiKey: CPJJLGSNPKSIJC-RSAXXLAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  12
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  Phenylmagnesium Iodide  在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 15.0h， 生成 (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline hydrochloride
  参考文献：
  名称：

  An Enantioselective Access to 1-Alkyl-1,2-Dihydroisoquinolines and 1-Alkyl-, 3-Alkyl-, and 1,3-Dialkyl-1,2,3,4-tetrahydroisoquinolines

  摘要：

  New chiral isoquinolinium salt derivatives 1, 2 or 3 have been treated with Grignard reagents to give as major products, 1-substituted 1,2-dihydroisoquinolines 4a-f, oxazolidine derivatives 10a-f or 21, respectively, in good yield and in moderate to good diastereoisomeric excess. The stereochemistry of these new derivatives has been elucidated, in particular, by X-ray crystallographic studies of 1,2-dihydroisoquinoline 4b and the minor oxazolidine 11b. Reduction of all these intermediates gave chiral 1-substituted 1,2,3,4-tetrahydroisoquinolines such as base 8. The enantioselective synthesis of the natural alkaloid (-)-salsonidine in three steps and 38% overall yield from salt 3 is described as an application. Reduction of salt 2 gave a new oxazolidine derivative 15 which is a practical intermediate for the synthesis of 3-alkyl 1,2,3,4-tetrahydroisquinolines 17a,b, while oxazolidines such as 10 are convenient precursors of 1,3-disubstituted tetrahydroisoquinolines, as illustrated by a synthesis of 1,3-dimethyl tetrahydroisoquinoline 20.

  DOI：

  10.1021/jo970768a

文献信息

• METHOD FOR THE PREPARATION OF SOLIFENACIN
  申请人：Jirman Josef

  公开号：US20100145055A1

  公开（公告）日：2010-06-10

  A method of preparing (1S)-(3R)-1-azabicyclo[2.2.2]oct-3-yl 3,4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate (solifenacin) or its pharmaceutically acceptable salts with high optic purity, wherein the crude solifenacin base is transformed to the hydrogen tartrate, which is then optionally transformed to another pharmaceutically acceptable salt or the base of solifenacin. A crystalline salt of solifenacin hydrogen tartrate.

  一种制备（1S）-（3R）-1-azabicyclo[2.2.2]辛-3-基 3,4-二氢-1-苯基-2(1H)-异喹啉羧酸酯（索利那辛）或其具有高光学纯度的药用盐的方法，其中粗索利那辛碱转化为酒石酸氢盐，然后可选择将其转化为另一种药用盐或索利那辛碱。索利那辛酒石酸氢盐的结晶盐。
• EP1714965
  申请人：——

  公开号：——

  公开（公告）日：——
• A METHOD FOR THE PREPARATION OF SOLIFENACIN
  申请人：Zentiva, k.s.

  公开号：EP2094693B1

  公开（公告）日：2011-11-16
• [EN] A METHOD FOR THE PREPARATION OF SOLIFENACIN<br/>[FR] PROCÉDÉ DE PRÉPARATION DE LA SOLIFÉNACINE
  申请人：ZENTIVA AS

  公开号：WO2008077357A2

  公开（公告）日：2008-07-03

  [EN] A method of preparing (lS)-(3R)-l-azabicyclo[2.2.2]oct-3-yl 3,4-dihydro-l-phenyl-2(lH)- isoquinoline carboxylate (solifenacin) or its pharmaceutically acceptable salts with high optic purity, wherein the crude solifenacin base is transformed to the hydrogen tartrate, which is then optionally transformed to another pharmaceutically acceptable salt or the base of solifenacin. A crystalline salt of solifenacin hydrogen tartrate.
  [FR] L'invention concerne un procédé de préparation du (1S)-(3R)-1-azabicyclo[2.2.2]oct-3-yl 3,4-dihydro-1-phényl-2(1H)-isoquinoléine carboxylate (solifénacine) ou de ses sels acceptables du point de vue pharmaceutique avec une pureté optique élevée, la base de solifénacine brute étant transformée en tartrate d'hydrogène, lequel est alors facultativement transformé en un autre sel acceptable du point de vue pharmaceutique ou en une base de la solifénacine. L'invention concerne également un sel cristallin de tartrate d'hydrogène de solifénacine.
• An Enantioselective Access to 1-Alkyl-1,2-Dihydroisoquinolines and 1-Alkyl-, 3-Alkyl-, and 1,3-Dialkyl-1,2,3,4-tetrahydroisoquinolines
  作者：Denis Barbier、Christian Marazano、Claude Riche、Bhupesh C. Das、Pierre Potier

  DOI：10.1021/jo970768a

  日期：1998.3.1

  New chiral isoquinolinium salt derivatives 1, 2 or 3 have been treated with Grignard reagents to give as major products, 1-substituted 1,2-dihydroisoquinolines 4a-f, oxazolidine derivatives 10a-f or 21, respectively, in good yield and in moderate to good diastereoisomeric excess. The stereochemistry of these new derivatives has been elucidated, in particular, by X-ray crystallographic studies of 1,2-dihydroisoquinoline 4b and the minor oxazolidine 11b. Reduction of all these intermediates gave chiral 1-substituted 1,2,3,4-tetrahydroisoquinolines such as base 8. The enantioselective synthesis of the natural alkaloid (-)-salsonidine in three steps and 38% overall yield from salt 3 is described as an application. Reduction of salt 2 gave a new oxazolidine derivative 15 which is a practical intermediate for the synthesis of 3-alkyl 1,2,3,4-tetrahydroisquinolines 17a,b, while oxazolidines such as 10 are convenient precursors of 1,3-disubstituted tetrahydroisoquinolines, as illustrated by a synthesis of 1,3-dimethyl tetrahydroisoquinoline 20.