1,2,3,4-Tetrahydro-7-methoxy-2-methyl-4-phenylisochinolin | 59645-78-2

• 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: 1,2,3,4-Tetrahydro-7-methoxy-2-methyl-4-phenylisochinolin
• 英文别名: 7-methoxy-2-methyl-4-phenyl-1,2,3,4-tetrahydro-isoquinoline；(+)-7-Methoxy-2-methyl-4-phenyl-1,2,3,4-terahydro isoquinoline；7-methoxy-2-methyl-4-phenyl-3,4-dihydro-1H-isoquinoline
• CAS: 59645-78-2
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: DBOZEPCLJKANCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4-Tetrahydro-7-methoxy-2-methyl-4-phenylisochinolin 、 7-hydroxy-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline 、 、 hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride 在 (+)-7-Dimethylaminoethoxy-2-methyl-4-phenyl-1,2,3,4-tetrahydro isoquinoline 作用下， 以 水 为溶剂， 生成 (+)-7-Dimethylaminoethoxy-2-methyl-4-phenyl-1,2,3,4-tetrahydro isoquinoline
  参考文献：
  名称：

  Tetrahydroisoquinoline basic ethers and pharmaceutical compositions and

  摘要：

  化合物的公式(II)：##STR1##和其盐，其中R.sub.1是C.sub.1-6烷基，C.sub.3-6环烷基苯基，萘基，芳基烷基，取代苯基或取代萘基；R.sub.2是一个基团：##STR2##其中R.sub.6是氢原子或C.sub.1-6烷基，R.sub.7是氢原子或C.sub.1-6烷基，苯基，甲苯基或苄基，或R.sub.6与R.sub.7连接，使得NR.sub.6 R.sub.7基团是一个5-、6-或7-成员环，R.sub.8是氢原子或C.sub.1-4烷基或连接到R.sub.6形成吗啡环的一部分，R.sub.9和R.sub.10分别是氢原子或C.sub.1-4烷基；R.sub.3是氢原子或C.sub.1-6烷基或三氟甲基基团；R.sub.4是氢原子或C.sub.1-6烷基，苄基或苯基或含有2到7个碳原子的酰基基团，R.sub.5是氢原子或-C.sub.1-6烷基基团；发现这些化合物是情绪调节剂和厌食症剂。

  公开号：

  US04113869A1
• 作为产物：
  描述：

  2-[(3-Methoxyphenyl)methyl-methylamino]-1-phenylethanone 在 硫酸 、 锌 作用下， 生成 1,2,3,4-Tetrahydro-7-methoxy-2-methyl-4-phenylisochinolin
  参考文献：
  名称：

  A New Synthesis of 1,2,3,4-Tetrahydro-2-methyl-4-phenylisoquinolines

  摘要：

  在氢化钠的条件下，芳香醛1、甲胺和α-卤代苯乙酮2通过环化反应生成1,2,3,4-四氢-2-甲基-4-苯基异�quinolines 6，该环化反应使用硫酸和锌在甲醇中进行。

  DOI：

  10.1055/s-1990-26846

文献信息

• 4-Phenyl tetrahydroisoquinolines as dual norepinephrine and dopamine reuptake inhibitors
  作者：Anthony D. Pechulis、James P. Beck、Matt A. Curry、Mark A. Wolf、Arthur E. Harms、Ning Xi、Chet Opalka、Mark P. Sweet、Zhicai Yang、A. Samuel Vellekoop、Andrew M. Klos、Peter J. Crocker、Carla Hassler、Mia Laws、Douglas B. Kitchen、Mark A. Smith、Richard E. Olson、Shuang Liu、Bruce F. Molino

  DOI：10.1016/j.bmcl.2012.09.050

  日期：2012.12

  Novel 4-phenyl tetrahydroisoquinolines that inhibit both dopamine and norepinephrine transporters were designed and prepared. In this Letter, we describe the synthesis, in vitro activity and associated structure-activity relationships of this series. We also report the ex vivo NET occupancy of a representative compound, 41. (C) 2012 Elsevier Ltd. All rights reserved.
• New Reduction Reaction of Benzylic Alcohols with Acid and Proof of the Intermolecular Hydride Shift Mechanism
  作者：Masaru Kihara、Jun-ichi Andoh、Chiaki Yoshida

  DOI：10.3987/com-99-8786

  日期：——

  The new reduction reaction of the hydroxy groups of 4-hydroxy-4-phenyl-1,2,3,4-tetrahydroisoquinolines (1) to the corresponding alkanes (2) with mineral and Lewis acids is reported. A stereoselective intermolecular hydride shift mechanism of the reduction was proved by reaction of the deuterated derivateives (14 and 15) of 1a with 10N HCl-C2H5OH and BBr3 in CH3CN.
• US4113869A
  申请人：——

  公开号：US4113869A

  公开（公告）日：1978-09-12
• A New Synthesis of 1,2,3,4-Tetrahydro-2-methyl-4-phenylisoquinolines
  作者：Atanas P. Venkov、Daniel M. Vodenicharov

  DOI：10.1055/s-1990-26846

  日期：——

  1,2,3,4-Tetrahyro-2-methyl-4-phenylisoquinolines 6 are obtained from aromatic aldehydes 1, methyl amine and α-haloacetophenones 2 in the presence of sodium borohydride followed by cyclization with sulfuric acid and zinc in methanol.

  在氢化钠的条件下，芳香醛1、甲胺和α-卤代苯乙酮2通过环化反应生成1,2,3,4-四氢-2-甲基-4-苯基异�quinolines 6，该环化反应使用硫酸和锌在甲醇中进行。
• Tetrahydroisoquinoline basic ethers and pharmaceutical compositions and
  申请人：Beecham Group Limited

  公开号：US04113869A1

  公开（公告）日：1978-09-12

  Compounds of the formula (II): ##STR1## and salts thereof wherein R.sub.1 is a C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl phenyl, naphthyl, aralkyl, substituted phenyl or substituted naphthyl group; R.sub.2 is a group: ##STR2## wherein R.sub.6 is a hydrogen atom or a C.sub.1-6 alkyl group, R.sub.7 is a hydrogen atom or a C.sub.1-6 alkyl, phenyl, tolyl, or benzyl group or R.sub.6 is linked to R.sub.7 so that the NR.sub.6 R.sub.7 moiety is a 5-,6- or 7- membered ring, R.sub.8 is a hydrogen atom or a C.sub.1-4 alkyl group or is joined to R.sub.6 to form part of a morpholino ring and R.sub.9 and R.sub.10 are each hydrogen atoms or C.sub.1-4 alkyl groups; R.sub.3 is a hydrogen atom or a C.sub.1-6 alkyl or a trifluoromethyl group; R.sub.4 is a hydrogen atom or a C.sub.1-6 alkyl, benzyl or phenyl group or an acyl group containing from 2 to 7 carbon atoms and R.sub.5 is a hydrogen atom or a -C.sub.1-6 alkyl group; have been found to be mood modifying agents and anorexia agents.

  化合物的公式(II)：##STR1##和其盐，其中R.sub.1是C.sub.1-6烷基，C.sub.3-6环烷基苯基，萘基，芳基烷基，取代苯基或取代萘基；R.sub.2是一个基团：##STR2##其中R.sub.6是氢原子或C.sub.1-6烷基，R.sub.7是氢原子或C.sub.1-6烷基，苯基，甲苯基或苄基，或R.sub.6与R.sub.7连接，使得NR.sub.6 R.sub.7基团是一个5-、6-或7-成员环，R.sub.8是氢原子或C.sub.1-4烷基或连接到R.sub.6形成吗啡环的一部分，R.sub.9和R.sub.10分别是氢原子或C.sub.1-4烷基；R.sub.3是氢原子或C.sub.1-6烷基或三氟甲基基团；R.sub.4是氢原子或C.sub.1-6烷基，苄基或苯基或含有2到7个碳原子的酰基基团，R.sub.5是氢原子或-C.sub.1-6烷基基团；发现这些化合物是情绪调节剂和厌食症剂。