3,7-difluoro-10,11-dihydro-5H-dibenzocyclohepten-5-one | 125025-34-5

• 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: 3,7-difluoro-10,11-dihydro-5H-dibenzocyclohepten-5-one
• 英文别名: 3,7-difluorodibenzosuberone；3,7-Difluoro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one；5,14-difluorotricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-one
• CAS: 125025-34-5
• 化学式: C₁₅H₁₀F₂O
• 分子量: 244.241
• InChiKey: MGXLRXDQFDWEJE-UHFFFAOYSA-N

物化性质

• 熔点：
  99-105 °C
• 沸点：
  364.6±42.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,7-difluoro-10,11-dihydro-5H-dibenzocyclohepten-5-one 在 二氯乙酸 、 N-溴代丁二酰亚胺(NBS) 、 盐酸羟胺 、 potassium tert-butylate 、 sodium acetate 、 溶剂黄146 、 sodium iodide 、 锌 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 丙酮 、 甲苯 为溶剂， 反应 135.25h， 生成 3,7-difluoro-5-methyl-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of a series of dibenzo[a,d]cycloalkenimines as N-methyl-D-aspartate antagonists

  摘要：

  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.

  DOI：

  10.1021/jm00164a052
• 作为产物：
  描述：

  10,11-二氢二苯并[a,b]环庚烯-5-酮 在 盐酸 、 硫酸 、 硝酸 、 溶剂黄146 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 重水 为溶剂， 反应 9.0h， 生成 3,7-difluoro-10,11-dihydro-5H-dibenzocyclohepten-5-one
  参考文献：
  名称：

  Scalable Synthesis of Strained Cyclooctyne Derivatives

  摘要：

  Modifications to the Popik synthesis of aza-dibenzocyclooctyne (DIBAC) derivatives are described, which avoids tedious purifications and dramatically improves the yield. A new and analogous route to biarylazacyclooctynone (BARAC) through an amide disconnection was also attempted. The BARAC derivatives prepared were found to be unstable under the conditions employed, undergoing a known rearrangement. Finally, the synthesis of a difluoro-DIBAC derivative with a second-order rate constant intermediate between DIBAC and BARAC derivatives (0.50 M-1) is described. While more difficult to synthesize, this molecule was found to be considerably more stable than any BARAC derivatives that were prepared.

  DOI：

  10.1055/s-0033-1340509

文献信息

• Compounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases
  申请人：NPS Pharmaceuticals, Inc.

  公开号：US20020004522A1

  公开（公告）日：2002-01-10

  Method and compositions for treating a patient having a neurological disease or disorder, such as stroke, head trauma, spinal cord injury, spinal cord ischemia, ischemia- or hypoxia-induced nerve cell damage, epilepsy, anxiety, neuropsychiatric or cognitive deficits due to ischemia or hypoxia such as those that frequently occur as a consequence of cardiac surgery under cardiopulmonary bypass, or neurodegenerative diseases such as Alzheimer's Disease, Huntington's Disease, Parkinson's Disease, or amyotrophic lateral sclerosis (ALS).

  本发明涉及一种用于治疗患有神经系统疾病或障碍的患者的方法和组合物，例如中风、头部创伤、脊髓损伤、脊髓缺血、缺血或缺氧引起的神经细胞损伤、癫痫、焦虑、神经精神或认知缺陷，由于缺血或缺氧而经常发生在心脏手术下心肺转流的后果，或神经退行性疾病，例如阿尔茨海默病、亨廷顿病、帕金森病或肌萎缩侧索硬化症（ALS）。
• THOMPSON, WAYNE J.;ANDERSON, PAUL S.;BRITCHER, SUSAN F.;LYLE, TERRY A.;TH+, J. MED. CHEM., 33,(1990) N, C. 789-808
  作者：THOMPSON, WAYNE J.、ANDERSON, PAUL S.、BRITCHER, SUSAN F.、LYLE, TERRY A.、TH+

  DOI：——

  日期：——
• US6211245B1
  申请人：——

  公开号：US6211245B1

  公开（公告）日：2001-04-03
• US6750244B2
  申请人：——

  公开号：US6750244B2

  公开（公告）日：2004-06-15
• US7087765B2
  申请人：——

  公开号：US7087765B2

  公开（公告）日：2006-08-08