N-(Methoxy)-5-methyl-5H-dibenzocycloheptene-5-amine | 89442-05-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: N-(Methoxy)-5-methyl-5H-dibenzocycloheptene-5-amine
• 英文别名: N-methoxy-5-methyl-5H-dibenzocycloheptene-5-amine；5-methyl-5-(methoxyamino)-5H-dibenzocycloheptene；N-methoxy-2-methyltricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-amine
• CAS: 89442-05-7
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: PGECQHZQBPMLIB-UHFFFAOYSA-N

物化性质

• 熔点：
  118.5-126.0 °C
• 沸点：
  370.2±52.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(Methoxy)-5-methyl-5H-dibenzocycloheptene-5-amine 在 sodium hydride 作用下， 生成 8b,8c-dihydro-4b-methyl-4bH-azirino<2,1,3-c,d>dibenzopyrrolizine
  参考文献：
  名称：

  Synthesis of (5R,10S,11R)-(+)-10,11-dihydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imin-11-ol: a hydroxylated metabolite of MK-0801

  摘要：

  DOI：

  10.1021/jo00288a050
• 作为产物：
  描述：

  5-二苯并环庚烯酮 在 二氯乙酸 、 NaO₂CH₃ 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.5h， 生成 N-(Methoxy)-5-methyl-5H-dibenzocycloheptene-5-amine
  参考文献：
  名称：

  Synthesis of (5R,10S,11R)-(+)-10,11-dihydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imin-11-ol: a hydroxylated metabolite of MK-0801

  摘要：

  DOI：

  10.1021/jo00288a050

文献信息

• Cyclization of electrochemically generated nitrogen radicals. A novel synthesis of 11-substituted dibenzo[a,d]cycloheptenimines
  作者：Sandor Karady、Edward G. Corley、Newton L. Abramson、Leonard M. Weinstock

  DOI：10.1016/s0040-4039(00)99645-x

  日期：1989.1

  A convenient synthesis of 11-substituted dibenzo[a,d]cycloheptenimines proceeding via annelation of electrochemically generated nitrogen radicals is described.

  描述了一种方便的合成11-取代的二苯并[a，d]环庚亚胺的方法，该方法是通过电化学生成的氮自由基的成环反应进行的。
• Derivatives of 5-methyl-10,11-dihydro-5H-dibenzo-(a,d) cyclohepten-5,10-imine
  申请人：Merck & Co., Inc.

  公开号：EP0264183A1

  公开（公告）日：1988-04-20

  Fluoro-and hydroxy-derivatives of 5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines wherein the substituents are on non-benzenoid carbons are active anticonvulsants and antagonists of N-methyl-D-aspartate.

  5-甲基-10,11-二氢-5H-二苯并[a,d]环庚烯-5,10-亚胺的氟衍生物和羟基衍生物（其中取代基位于非苯碳原子上）是活性抗惊厥药和 N-甲基-D-天冬氨酸拮抗剂。
• Synthesis and pharmacological evaluation of a series of dibenzo[a,d]cycloalkenimines as N-methyl-D-aspartate antagonists
  作者：Wayne J. Thompson、Paul S. Anderson、Susan F. Britcher、Terry A. Lyle、J. Eric Thies、Catherine A. Magill、Sandor L. Varga、John E. Schwering、Paulette A. Lyle

  DOI：10.1021/jm00164a052

  日期：1990.2

  A series of 73 dibenzo[a,d]cycloalkenimines were synthesized and evaluated for their ability to displace (+)-10,11-dihydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imine ([3H]-(+)-10) from its specific binding site on rat cortical membranes. A number of the more active compounds (Ki ranging from 0.006 to 0.21 microM) were evaluated for N-methyl-D-aspartate (NMDA) antagonist activity in the rat cortical slice (Kb ranging from 0.08 to 0.9 microM) and anticonvulsant activity in the mouse against NMDA induced convulsions. The ED50 values ranged from 0.22 to 7.76 mg/kg and correlated reasonably well with the Kb determination. In the dibenzo[a,d]cyclohepten-5,10-imine series, the (+)-5S,10R enantiomer displayed consistently higher levels of biological activity. While substitution at the 3-position of (+)-10 with electronegative atoms generally increased in vitro activity, a loss of potency relative to (+)-10 (MK-801) was observed in vivo for all of the compounds tested.
• .alpha.-Effect nucleophiles: a novel and convenient method for the synthesis of dibenzo[a,d]cycloheptenimines
  作者：Theresa Rothauser Lamanec、Dean R. Bender、Anthony M. DeMarco、Sandor Karady、Robert A. Reamer、Leonard M. Weinstock

  DOI：10.1021/jo00243a031

  日期：1988.4
• Cyclization of electrochemically generated nitrogen radicals.
  作者：Sandor Karady、Edward G. Corley、Newton L. Abramson、Joseph S. Amato、Leonard M. Weinstock

  DOI：10.1016/s0040-4020(01)87065-4

  日期：1991.1

  A novel and convenient synthesis of 11-substituted dibenzo[a,d]cycloheptimines 10 via annelation of electrochemically generated aminium radicals derived from substituted 5-hydroxylamino-5-methyl-5H-dibenzo[a,d]cycloheptenes 14 is described. The scope and limitations of the reaction as well as the effects of reactor design, current density and electrode material on the yield of 10 and the carbocation rearrangement by-product 28 are discussed.