5,7-dihydro-dibenzo[a,c]cyclohepten-6-one | 1139-82-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 5,7-dihydro-dibenzo[a,c]cyclohepten-6-one
• 英文别名: 6H-5,7-Dihydro-dibenzocyclohepten-6-one；5,7-Dihydro-dibenzo[a,c]cyclohepten-6-on；1.2;3.4-Dibenzo-cycloheptadien-(1.3)-on-(6)；5,7-dihydro-6H-dibenzo[a,c]cyclohepten-6-one；6H-Dibenzo(a,c)cyclohepten-6-one, 5,7-dihydro-；tricyclo[9.4.0.02,7]pentadeca-1(15),2,4,6,11,13-hexaen-9-one
• CAS: 1139-82-8
• 化学式: C₁₅H₁₂O
• 分子量: 208.26
• InChiKey: YGWVVRDRBWXLNX-UHFFFAOYSA-N

物化性质

• 熔点：
  78 °C(Solv: ethanol (64-17-5))
• 沸点：
  307.46°C (rough estimate)
• 密度：
  1.0459 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 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：
  1

反应信息

• 作为反应物：
  描述：

  5,7-dihydro-dibenzo[a,c]cyclohepten-6-one 在 potassium fluoride on basic alumina 、 对甲苯磺酰叠氮 作用下， 以 乙腈 为溶剂， 反应 96.0h， 以75%的产率得到5,7-Bis(diazo)-1,2,3,4-dibenzocyclohepta-1,3-dien-6-one
  参考文献：
  名称：

  Synthesis and Photochemistry of 5,7-Bis(diazo)-1,2,3,4-dibenzocyclohepta-1,3-dien-6-one. Generation and Reactions of Phenanthrenodiazacyclopentadiene, Phenanthrenocyclopropenone, and 9,10-Phenanthryne

  摘要：

  The title compound 15 was prepared as the first 1,3-bis(diazo) ketone incorporated into a seven-membered ring, and its photochemical pathways were investigated not only by product analysis study but also by using matrix isolation spectroscopy. Irradiation of 15 in alcoholic solvents gave 9-(alkoxycarbonyl)phenanthrene 16 as a main product, while similar irradiation in non-nucleophilic solvents provided diphenanthreno-syn-1,5-diazabicyclo[3.3.0]octadienedione (20), The formation of these products is interpreted as indicating that 15 eliminates one of two diazo functions upon photoexcitation to form 9-diazo-10-carbonylphenanthrene (21) which either reacts with alcohol by eliminating the second dinitrogen, leading to 16, or undergoes dimerization to form 20. Photolysis of 15 in an ethanol matrix at 77 K gave 9-ethoxyphenanthrene (31) as a new product along with 16. Irradiation of 15, matrix-isolated in Ar at 10 K monitored by IR, indicated that phenanthrenocyclopropenone (28) was formed as an initial product which then underwent photodecarbonylation to leave 9,10-phenanthryne (32), and that 32 reacted with CO to reproduce 28 upon photoexcitation. The cyclopropenone (28) was shown to be generated also by photolysis of 9,10-dicarboxyphenanthrene anhydride (33) in Ar matrix at 10 K. A plausible mechanism to explain the observed sequential decomposition of the two diazo functions in the room temperature photolytic run and the formal simultaneous elimination of two dinitrogens in the low temperature matrix run is proposed.

  DOI：

  10.1021/jo00113a011
• 作为产物：
  描述：

  1-amino-2-cyano-3,4:5,6-dibenzocycloheptatriene 在 磷酸 、 硫酸 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 16.0h， 生成 5,7-dihydro-dibenzo[a,c]cyclohepten-6-one
  参考文献：
  名称：

  1-Phenyl-3,4:5,6-dibenzocycloheptatrienyl anion. A stable antiaromatic carbanion

  摘要：

  DOI：

  10.1021/jo00145a043
• 作为试剂：
  描述：

  5,7-dihydro-dibenzo[a,c]cyclohepten-6-one 、 亚硝酸丁酯 、 盐酸 在 5,7-dihydro-dibenzo[a,c]cyclohepten-6-one 、 乙醚 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 5-Amino-5,7-dihydro-6H-dibenzo[a,c]cyclohepten-6-ol Hydrochloride
  参考文献：
  名称：

  Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting B-amyloid peptide release and/or its synthesis by use of such compounds

  摘要：

  本发明涉及抑制β-淀粉样肽释放和/或其合成的化合物，因此具有治疗阿尔茨海默病的用途。还公开了包含抑制β-淀粉样肽释放和/或其合成的化合物的药物组合物，以及使用这种药物组合物预防和治疗阿尔茨海默病的方法。

  公开号：

  US20020052359A1

文献信息

• Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds
  申请人：——

  公开号：US20020045747A1

  公开（公告）日：2002-04-18

  Disclosed are compounds which inhibit &bgr;-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits &bgr;-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

  公开了抑制β-淀粉样肽释放和/或其合成的化合物，因此可用于治疗阿尔茨海默病。还公开了包含抑制β-淀粉样肽释放和/或其合成的化合物的药物组合物，以及使用这些药物组合物预防性和治疗性治疗阿尔茨海默病的方法。
• Novel reactions of the low valent cobalt reagent generated using CoCl2 and NaBH4/C2H5OH in the presence of carbon monoxide
  作者：Nistala Satyanarayana、Mariappan Periasamy

  DOI：10.1016/0022-328x(87)85165-3

  日期：1987.10

  Low valent cobalt species, prepared in situ in tetrahydrofuran (THF) by the reduction of CoCl2 with NaBH4/C2H5OH under carbon monoxide, isomerize of alkenes, reduce alkenes, and carbonylate benzyl halides under appropriate conditions.

  低价钴物种，是通过在一氧化碳下用NaBH 4 / C 2 H 5 OH还原CoCl 2在四氢呋喃（THF）中原位制备的，烯烃的异构化，还原烯烃，以及在适当条件下羰基化苄基卤。
• Excited state carbon acid dissociation and competing photorearrangements of 5<i>H</i>-dibenzo[a,c]cycloheptene derivatives
  作者：David. Budac.、Peter Wan

  DOI：10.1139/v96-162

  日期：1996.8.1

  dissociating excited state carbon acids were reported by our group. A necessary structural feature is the 5H-dibenzocycloheptene ring system where the incipient carbanion is formally an antiaromatic system in S0. In this work, structure–reactivity studies of the excited singlet state carbon acid dissociation and competing formal di-π-methane rearrangement of several 5H-dibenzo[a,c]cycloheptene derivatives

  我们小组报告了解离激发态碳酸的第一个例子。一个必要的结构特征是 5H-二苯并环庚烯环系统，其中初始碳负离子在形式上是 S0 中的反芳香系统。在这项工作中，对几种 5H-二苯并[a,c] 环庚烯衍生物的激发单重态碳酸解离和竞争性形式二-π-甲烷重排进行了结构-反应性研究，以获得对光化学的更多见解由这些化合物显示。7-deuterio-5H-dibenzo[a,c]cycloheptene (9) 在水溶液中的光解表明光生碳负离子是烯丙基离域的。发现衍生物 7 在碳酸解离方面的反应性低于 3，而 8 没有反应性。乙醇胺（在 CH3CN 中）被发现是一种有效的碱，可催化 3、7 和 9 的碳酸解离，如更高的氘掺入产率和荧光猝灭率所示。双萘...
• Simple syntheses of Co2(CO)8 and NaCo(CO)4 reagents by the reduction of CoCl2 (or CoBr2) under carbon monoxide at atmospheric pressure
  作者：A. Devasagayaraj、S. Achyutha Rao、M. Periasamy

  DOI：10.1016/0022-328x(91)86487-b

  日期：1991.2

  The reduction of CoCl2 by MgH2 in tetrahydrofuran in the presence of carbon monoxide gives Co2(CO)8, which on treatment with an alkyne and norbornene gives the Pauson−Khand reaction. The reduction of CoCl2 or CoBr2 by sodium naphthalenide in THF in the presence of carbon monoxide gives NaCo(CO)4, which has been used for cyclization of certain benzylic halides into the corresponding cyclic ketones.

  在一氧化碳存在下，四氢呋喃中的MgH 2将CoCl 2还原，得到Co 2（CO）8，经炔烃和降冰片烯处理后，产生Pauson-Khand反应。在一氧化碳的存在下，萘甲酸钠在THF中用萘钠还原CoCl 2或CoBr 2，得到NaCo（CO）4，已用于将某些苄基卤化物环化为相应的环状酮。
• Aziridine formation by lithium aluminum hydride reduction of dibenzo[a.c.]cycloheptadien-6-one oxime
  作者：K. Kotera、M. Motomura、S. Miyazaki、T. Okada、Y. Matsukawa

  DOI：10.1016/s0040-4020(01)82479-0

  日期：1968.1

  LAH reduction of dibenzo[a.c.]cycloheptadien-6-one oxime (Ib) in refluxing THF gives an aziridine,5,6-imino-dbenzo[a.c.]cycloheptadiene (IIa), in good yield together with a small amount of the expected primary amine, 6-amino-dibenzo[a.c.]cycloheptadiene (IIIa). The structure of the aziridine has been established by a reliable synthesis through an addition of iodine isocyanate to dibenzo[a.c.]cyclo-heptatriene

  在回流的THF中用LAH还原二苯并[ac]环庚二烯-6-肟（Ib），得到氮丙啶5,6-亚氨基-d-苯并[ac]环庚二烯（IIa），收率很高，并有少量预期的伯胺胺，6-氨基-二苯并[ac]环庚二烯（IIIa）。通过将异氰酸碘加到二苯并[ac]环-庚三烯（V）中，可以可靠地合成氮丙啶的结构。氮丙啶与酸的开环反应已经进行。氮丙啶的产率取决于反应中使用的溶剂和温度。