5,5-dimethoxy-5H-dibenzocycloheptene | 1087-68-9

• 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: 5,5-dimethoxy-5H-dibenzocycloheptene
• 英文别名: dibenzocycloheptenone dimethyl ketal；5,5-dimethoxy-5H-dibenzo[a,d]cycloheptene；5,5-Dimethoxy-5H-dibenzocyclohepten；Dibenzocycloheptatrienon-dimethylacetal；2,2-Dimethoxytricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaene
• CAS: 1087-68-9
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: JKYFTTRCVXHJJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5-dimethoxy-5H-dibenzocycloheptene 在 二甲基溴化硼 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以93%的产率得到5-二苯并环庚烯酮
  参考文献：
  名称：

  溴化二甲基硼和溴化二苯硼。缩醛和缩酮裂解。裂解MEM，MOM和MTM醚。

  摘要：

  描述了通过使用二甲基溴化硼或二苯基溴化硼裂解乙缩醛和缩酮的通用且有效的方法。在相似的反应条件下，MEM，MOM和MTM醚也会反应，以优异的收率得到母体醇。

  DOI：

  10.1016/s0040-4039(00)88238-6
• 作为产物：
  描述：

  4-Brom-2,3:6,7-dibenzo-cycloheptatrienon-dimethylacetal 生成 5,5-dimethoxy-5H-dibenzocycloheptene
  参考文献：
  名称：

  Tochtermann,W. et al., Justus Liebigs Annalen der Chemie, 1967, vol. 705, p. 169 - 184

  摘要：

  DOI：

文献信息

• New Synthetic Route to 10,11-Dihydro-5<i>H</i>-dibenzo[<i>a</i>,<i>d</i>]cyclohepten-5,10-imines through Photoamination of 5-Alkoxy- and 5-Hydroxy-5<i>H</i>-dibenzo[<i>a</i>,<i>d</i>]cycloheptenes Followed by a Transannular Reaction with Acetic Acid
  作者：Masahide Yasuda、Tomoko Wakisaka、Ryuji Kojima、Kimiko Tanabe、Kensuke Shima

  DOI：10.1246/bcsj.68.3169

  日期：1995.11

  The photoadditions of ammonia and alkylamines (RNH2) to 5-hydroxy- and 5-alkoxy-5H-dibenzo[a,d]cycloheptene derivatives (2) occurred at the C10–C11 double bond upon the irradiation of 2 with RNH2 in the presence of p-dicyanobenzene. The resulting 5-substituted 10-alkylamino-10,11-dihydro-5H-dibenzo[a,d]cycloheptenes were converted to 5-substituted N-alkyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines by a treatment with AcOH.

  氨和烷基胺（RNH2）对5-羟基和5-烷氧基-5H-二苯并[a,d]环庚烯衍生物（2）的加成发生在C10-C11双键处，这是在存在对二氰基苯的情况下，通过RNH2对2进行辐照实现的。所得到的5-取代的10-烷基氨基-10,11-二氢-5H-二苯并[a,d]环庚烯通过与AcOH处理，转化为5-取代的N-烷基-10,11-二氢-5H-二苯并[a,d]环庚烯-5,10-亚胺。
• 一种二甲氧基二苯并环庚烯的合成方法
  申请人：河南工程学院

  公开号：CN107501052B

  公开（公告）日：2020-09-18

  一种二甲氧基二苯并环庚烯的合成方法，包括以下步骤：1）先将二苯并环庚烯酮和溶剂混合，通入保护气，搅拌下并于30～50min内分批加入锂盐，加毕搅拌20～40min；再将体系升温至70～100℃，加压至2～4个大气压，加入甲酯反应4～6h，之后体系升温至120～150℃，加压至6～8个大气压，继续反应8～13h；2）反应后，体系冷却，加入乙酸乙酯过滤，滤液经无水硫酸钠干燥后，蒸干溶剂得产物。本发明在锂盐催化、加热和加压条件下，二苯并环庚烯酮可直接与甲酯反应生成目标产物，发明的步骤少，整体工艺简单，产物产率高。
• Dimethylboron bromide and diphenylboron bromide: cleavage of acetals and ketals
  作者：Yvan Guindon、Christiane Yoakim、Howard E. Morton

  DOI：10.1021/jo00195a007

  日期：1984.10
• Carbene cation radicals: the kinetics of their formation from diazoalkane cation radicals and their reactions
  作者：Vernon D. Parker、Donald Bethell

  DOI：10.1021/ja00251a002

  日期：1987.8
• Analogs of the dioxolanes dexoxadrol and etoxadrol as potential phencyclidine-like agents. Synthesis and structure activity relationships
  作者：Andrew Thurkauf、Mariena V. Mattson、Scott Richardson、Seid Mirsadeghi、Paul L. Ornstein、Ernest A. Harrison、Kenner C. Rice、Arthur E. Jacobson、James A. Monn

  DOI：10.1021/jm00086a001

  日期：1992.4

  A series of dioxolane analogues based on dexoxadrol ((4S,6S)-2,2-diphenyl-4-(2-piperidyl)-1,3-dioxolane) and etoxadrol ((2S,4S,6S)-2-ethyl-2-phenyl-4-(2-piperidyl)-1,3-dioxolane) were prepared and tested for their ability to displace [H-3]TCP (1-[1-(2-thienyl)cyclohexyl]piperidine) from PCP (1-(1-phenylcyclohexyl)piperidine) binding sites in rat brain tissue homogenates. Qualitative structure-activity relationships within this series were explored through modifications of the three major structural units of dexoxadrol, the piperidine, 1,3-dioxolane, and aromatic rings of the molecule. N-Alkyl derivatives of dexoxadrol were found to be inactive, as were those analogues where the dioxolane ring was modified. Phenyl-substituted etoxadrol analogues were compared to similarly substituted PCP analogues and distinct differences were found in their structure-activity relationships suggesting that the aromatic rings in these two drug classes interact differently with the PCP binding sites. The replacement of the phenyl ring in etoxadrol by either a 2- or 3-thienyl ring led to compounds with affinity comparable to etoxadrol, and the replacement of the ethyl moiety on etoxadrol's dioxolane ring with propyl (7) or isopropyl (8) led to compounds which were more potent than etoxadrol or PCP. The most potent compound was (2S,4S,6S)-2-ethyl-2-(1-chlorophenyl)-4-(2-piperidyl)-1,3-dioxolane (11), where a chlorine moiety was placed in the ortho position in the aromatic ring of etoxadrol. Its potency was comparable with TCP in vitro.