2,3,4,5-tetrahydro-3-methyl-1-phenyl-1H-3-benzoazepine | 129666-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 2,3,4,5-tetrahydro-3-methyl-1-phenyl-1H-3-benzoazepine
• 英文别名: 3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine；3-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine；3-Methyl-5-phenyl-1,2,4,5-tetrahydro-3-benzazepine
• CAS: 129666-25-7
• 化学式: C₁₇H₁₉N
• 分子量: 237.345
• InChiKey: GVNDJLHSESBPRV-UHFFFAOYSA-N

物化性质

• 熔点：
  73-75 °C
• 沸点：
  356.1±11.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-cyanomethyl-2-methyl-1,2,3,4-tetrahydroisoquinolinium chloride 在 sodium tetrahydroborate 、 仲丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正戊烷 为溶剂， 反应 6.0h， 生成 2,3,4,5-tetrahydro-3-methyl-1-phenyl-1H-3-benzoazepine
  参考文献：
  名称：

  Aryne-Mediated Arylation of the 3-Benzazepine Scaffold: One-Pot Synthesis of 1-Aryl-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepines

  摘要：

  The coupling of beta-amino carbanions derived from 3-benzazepines with in situ generated arynes has been demonstrated as a convenient route for the direct synthesis of a variety of 1-aryl-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepines, including the biologically active drug molecule SCH 12679.

  DOI：

  10.1055/s-0034-1380453

文献信息

• SUBSTITUTED GLYCINAMIDES, PROCESS FOR THEIR MANUFACTURE AND USE THEREOF AS MEDICAMENTS
  申请人：Priepke Henning

  公开号：US20100216769A1

  公开（公告）日：2010-08-26

  The present invention relates to new substituted glycinamides of general formula (I) wherein D, M, R 3 , R 4 and R 5 are defined as in the specification, the tautomers, enantiomers, diastereomers, mixtures and salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable properties.

  本发明涉及一般式(I)的新取代甘氨酰胺，其中D、M、R3、R4和R5如规范中定义，其互变异构体、对映异构体、非对映异构体、混合物以及其盐，特别是其与无机或有机酸或碱形成的生理上可接受的盐，具有有价值的特性。
• Direct syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines via hydroamination of enol carbamates
  作者：José Crecente-Campo、M. Pilar Vázquez-Tato、Julio A. Seijas

  DOI：10.1016/j.tet.2009.01.098

  日期：2009.3

  An efficient and simple procedure for the syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines has been developed. The approach uses easily available starting materials and requires just three steps. The hydroamination of an enol carbamate is the key step. This general and direct method has been applied to the total synthesis of the natural alkaloid cherylline

  已经开发了一种有效而简单的合成4-芳基-1,2,3,4-四氢异喹啉和1-芳基-2,3,4,5-四氢-3-苯并a庚因的方法。该方法使用容易获得的起始材料，仅需三个步骤。烯醇氨基甲酸酯的加氢胺化是关键步骤。这种通用和直接的方法已经应用于天然生物碱cherylline的全合成以及具有生物活性的3-苯并a庚因。
• [EN] NOVEL PYRIDINYL ACRYLAMIDE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS D'ACRYLAMIDE DE PYRIDINYLE
  申请人：TOPOTARGET AS

  公开号：WO2010066709A1

  公开（公告）日：2010-06-17

  The present application discloses pyridinyl acrylamide derivatives of the formula (I) wherein X is opt.subst. pyrid-3-yl, pyrid-4-yl; A is -C(=O)-, -S(=O)2-, -C(=S)-, -P(=O)(R5)- (R5 is C1-6-alkyl, C1-6-alkoxy, hydroxy); B is a single bond, -O-; D is a single bond, -O-, -CR7R8-, -NR9-; m is 0-12, n is 0-12, m+n is 1-20. The compounds are useful for the inhibiting of the enzyme nicotinamide phosphoribosyltransferase (NAMPRT), and to medical use of such pyridinyl acrylamide derivatives.

  本申请公开了式(I)的吡啶基丙烯酰胺衍生物，其中X是选择性取代的吡啶-3-基，吡啶-4-基；A是-C（=O）-，-S（=O）2-，-C（=S）-，-P（=O）（R5）-（R5为C1-6烷基，C1-6烷氧基，羟基）；B是单键，-O-；D是单键，-O-，-CR7R8-，-NR9-；m为0-12，n为0-12，m+n为1-20。这些化合物用于抑制酶烟酰胺磷酸核糖转移酶（NAMPRT）的活性，并用于这种吡啶基丙烯酰胺衍生物的医药用途。
• NEW SUBSTITUTED GLYCINAMIDES, PROCESS FOR THEIR MANUFACTURE AND USE THEREOF AS MEDICAMENTS
  申请人：PRIEPKE Henning

  公开号：US20130184256A1

  公开（公告）日：2013-07-18

  The present invention relates to new substituted glycinamides of general formula (I) wherein D, M, R 3 , R 4 and R 5 are defined as in the specification, the tautomers, enantiomers, diastereomers, mixtures and salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable properties.

  本发明涉及一种新的取代的甘氨酰胺，其一般式为（I），其中D、M、R3、R4和R5如规范中所定义，其互变异构体、对映异构体、顺反异构体、混合物和盐，特别是与无机或有机酸或碱的生理上可接受的盐，具有有价值的性质。
• Rearrangements of 1,6,7-trisubstituted 2-methyl-1,2,3,4-tetrahydroisoquinolinium 2-methylides
  作者：Yoshiro Sato、Naohiro Shirai、Yoshio Machida、Emiko Ito、Takayo Yasui、Yukihisa Kurono、Keiichiro Hatano

  DOI：10.1021/jo00051a008

  日期：1992.12

  Chemical behavior of 1,6,7-trisubstituted 2-methyl-1,2,3,4-tetrahydroisoquinolinium 2-methylides 4 was investigated in fluoride-ion induced desilylation reaction of 1,6,7-trisubstituted 2-methyl-2-(trimethylsilyl)-methyl-1,2,3,4-tetrahydroisoquinolinium iodides 3. The 1-nonsubstituted (4a,b) and 1-alkyl-substituted ylides (4c,d) gave mixtures of five products (7-11), but the 1-phenyl-substituted analogues (4e,f) yielded (E)- and (Z)-2,3-disubstituted 5-benzylidene-1,3-cyclohexadiene-6-spiro-3'-1'-methylpyrrolidines (E)-5 and (Z)-5 and 7,8-disubstituted 3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines 6. The mechanisms of the rearrangement are discussed.