10,11-dihydro-12-H-dibenzo[a,d]cycloocten-5-one | 1022-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 10,11-dihydro-12-H-dibenzo[a,d]cycloocten-5-one
• 英文别名: 6,7-Dihydrodibenzocycloocten-12(5H)-on；Tricyclo[10.4.0.03,8]hexadeca-1(16),3,5,7,12,14-hexaen-2-one
• CAS: 1022-14-6
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: CSDMXUHLDVZABA-UHFFFAOYSA-N

物化性质

• 熔点：
  138-140 °C(Solv: isopropanol (67-63-0))
• 沸点：
  173-178 °C(Press: 0.8 Torr)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  10,11-dihydro-12-H-dibenzo[a,d]cycloocten-5-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 10,11-dihydro-12H-dibenzo[a,d]cycloocten-5-ol
  参考文献：
  名称：

  新的精神药物。IV。二苯并（A，D）（1,4）环十二碳二烯的衍生物。

  摘要：

  DOI：

  10.1021/jm00338a010
• 作为产物：
  描述：

  3-phenethyl-phthalide 在 磷化氢 、 PPA 、 氢碘酸 作用下， 生成 10,11-dihydro-12-H-dibenzo[a,d]cycloocten-5-one
  参考文献：
  名称：

  新的精神药物。IV。二苯并（A，D）（1,4）环十二碳二烯的衍生物。

  摘要：

  DOI：

  10.1021/jm00338a010

文献信息

• Experiments in the Colchicine Field. V. The Thermal and Photochemical Decomposition of Various 2-(β-Phenylethyl)-phenyldiazomethanes and 2-(γ-Phenylpropyl)-phenyldiazomethanes¹
  作者：C. David Gutsche、Emil F. Jason、Robert S. Coffey、Herbert E. Johnson

  DOI：10.1021/ja01554a043

  日期：1958.11
• New triazine derivatives as potent modulators of multidrug resistance
  作者：Alain Dhainaut、Gilbert Regnier、Ghanem Atassi、Alain Pierre、Stephane Leonce、Laurence Kraus-Berthier、Jean Francois Prost

  DOI：10.1021/jm00091a017

  日期：1992.6

  A series of 70 triazine derivatives have been synthesized and tested for their capacity to modulate multidrug resistance (MDR) in DC-3F/AD and KB-A1 tumor cells in vitro, in comparison with verapamil (VRP), a calcium channel antagonist currently used in therapy as an antihypertensive drug, which also shows MDR modulating activity. Among the 12 selected compounds, 16 (S9788) showed high MDR reversing properties in vitro (300- and 6-fold VRP at 5-mu-M in DC-3F/AD and KB-A1 cells, respectively) and induced a strong accumulation of adriamycin. The relationship between the increase of ADR accumulation and the fold reversal induced by these compounds and their lack of effects on the sensitive DC-3F cells suggest that they act mainly by inhibiting the P-glycoprotein (Pgp) catalyzed efflux of cytotoxic agents, as already described for a majority of MDR modulators. In vivo, in association with the antitumor drug vincristine (0.25 mg/kg), 16 (100 mg/kg) increased the TIC by 39% in mice bearing the resistant tumor cell line P388/VCR. According to these interesting properties, 16 was selected for a clinical development because it was more bioavailable than 34, even though it was less active.
• .beta.-Iodo Ketones by Prevost Reaction Of Vinyl Carbinols
  作者：Engelbert Ciganek、J. C. Calabrese

  DOI：10.1021/jo00119a021

  日期：1995.7

  Treatment of alpha-ethenyl-alpha-phenylbenzenemethanol with iodine and silver acetate in either acetic acid or benzene gave 1,2-diphenyl-3-iodo-1-propanone (6) in 85% yield. Ring enlargements involving similar rearrangements were observed with a number of cyclic vinyl carbinols. In some cases, mixtures of normal Prevost products and rearranged beta-iodo ketones were obtained. The exact scope of this apparently novel reaction remains to be elucidated. Treatment of the beta-iodo ketones with DBU gave the corresponding alpha,beta-unsaturated ketones from which a number of amino ketones and amino alcohols were prepared by conjugate addition followed by reduction.
• Banciu, Mircea D.; Drǎghici, Constantin; Popescu, Angela, Revue Roumaine de Chimie, 1998, vol. 43, # 7, p. 649 - 660
  作者：Banciu, Mircea D.、Drǎghici, Constantin、Popescu, Angela、Banciu, Anca、Simion, Alina

  DOI：——

  日期：——
• Transannular reactions of dibenzo[a,d]cycloalkenes. 2. Synthesis of bridgehead substituted dibenzo[a,d]cycloalkenimines by a regiospecific transannular amine to olefin addition
  作者：Ben E. Evans、Paul S. Anderson、Marcia E. Christy、C. Dylion Colton、David C. Remy、Kenneth E. Rittle、Edward L. Engelhardt

  DOI：10.1021/jo01332a008

  日期：1979.8