2-(benzyl-methyl-amino)-1-(4-chloro-phenyl)-ethanone | 131326-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(benzyl-methyl-amino)-1-(4-chloro-phenyl)-ethanone
• 英文别名: 2-(Benzyl-methyl-amino)-1-(4-chlor-phenyl)-aethanon；2-[Benzyl(methyl)amino]-1-(4-chlorophenyl)ethanone
• CAS: 131326-96-0
• 化学式: C₁₆H₁₆ClNO
• mdl: MFCD15481135
• 分子量: 273.762
• InChiKey: JRBKZWUVGVMEAX-UHFFFAOYSA-N

物化性质

• 沸点：
  395.7±27.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(benzyl-methyl-amino)-1-(4-chloro-phenyl)-ethanone 在 sodium tetrahydroborate 、 硫酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.83h， 生成 4-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  4-Phenyl tetrahydroisoquinolines as dual norepinephrine and dopamine reuptake inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2012.09.050
• 作为产物：
  描述：

  苯亚甲基甲胺 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 20.5h， 生成 2-(benzyl-methyl-amino)-1-(4-chloro-phenyl)-ethanone
  参考文献：
  名称：

  4-Phenyl tetrahydroisoquinolines as dual norepinephrine and dopamine reuptake inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2012.09.050

文献信息

• A convenient synthesis of 4-substituted 1,2,3,4-tetrahydroisoquinolin-4-ols by a novel intramolecular barbier reaction and by an insertion reaction: reaction scope and limitations
  作者：Masaru Kihara、Minoru Kashimoto、Yoshimaro Kobayashi

  DOI：10.1016/s0040-4020(01)80579-2

  日期：1992.1

  4-Substituted 1,2,3,4-tetrahydroisoquinolin-4-ols were prepared from -(2-iodobenzyl)phenacylamines by an intramolecular Barbier reaction with butyllithium and by an insertion reaction with zerovalent nickel. The scope and limitations of these reactions were discussed.

  由-（2-碘苄基）苯甲胺通过与丁基锂的分子内Barbier反应并通过与零价镍的插入反应制备4-取代的1,2,3,4-四氢异喹啉-4-醇。讨论了这些反应的范围和局限性。
• A new intramolecular barbier reaction of N-(2-iodobenzyl)phenacylamines: A convenient synthesis of 1,2,3,4-tetrahydroisoquinomn-4-ols
  作者：Masaru Kihara、Minoru Kashimoto、Yoshimaro Kobayashi、Shigeru Kobayashi

  DOI：10.1016/s0040-4039(00)98068-7

  日期：1990.1

  4-Phenyl-1,2,3,4-tetrahydroisoquinolin-4-ols were prepared by an intramolecular Barbier reaction of N-(2-iodobenzyl)phenacylamines with butyllithium in good yields.

  通过N-（2-碘苄基）苯胺与丁基锂的分子内Barbier反应以良好的收率制备4-苯基-1,2,3,4-四氢异喹啉-4-醇。
• ANTIMALARIALS. α-PHENYL-β-DIALKYLAMINO ALCOHOLS¹
  作者：ROBERT E. LUTZ、RUFUS K. ALLISON、GILBERT ASHBURN、PHILIP S. BAILEY、MARION T. CLARK、JOHN F. CODINGTON、ADOLF J. DEINET、JAMES A. FREEK、ROBERT H. JORDAN、NORMAN H. LEAKE、TELLIS A. MARTIN、KENT C. NICODEMUS、RUSSELL J. ROWLETT、NEWTON H. SHEARER、J. DOYLE SMITH、JAMES W. WILSON

  DOI：10.1021/jo01169a001

  日期：1947.9
• KIHARA, MASANU;KASHIMOTO, MINORU;KOBAYASHI, YOSHIMARO;KOBAYASHI, SHIGERU, TETRAHEDRON LETT., 31,(1990) N7, C. 5347-5348
  作者：KIHARA, MASANU、KASHIMOTO, MINORU、KOBAYASHI, YOSHIMARO、KOBAYASHI, SHIGERU

  DOI：——

  日期：——
• 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.