2,2'-(3''-chlorophenyl)methylene-bis(5,5-dimethylcyclohexane-1,3-dione) | 33742-93-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,2'-(3''-chlorophenyl)methylene-bis(5,5-dimethylcyclohexane-1,3-dione)
• 英文别名: 2-[(3-Chlorophenyl)-(4,4-dimethyl-2,6-dioxocyclohexyl)methyl]-5,5-dimethylcyclohexane-1,3-dione
• CAS: 33742-93-7
• 化学式: C₂₃H₂₇ClO₄
• 分子量: 402.918
• InChiKey: PBMBMRYDXPIPDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  68.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-(3''-chlorophenyl)methylene-bis(5,5-dimethylcyclohexane-1,3-dione) 生成 3,3,6,6-tetramethyl-9-(3-chlorophenyl)-1,8-dioxo-octahydroxanthene
  参考文献：
  名称：

  Aldonitrones as Aldehyde Equivalents: An Efficient, Green, and Novel Protocol for the Synthesis of 1,8-Dioxo-octahydroxanthenes

  摘要：

  A novel, self-catalyzed, solvent-free, microwave-enhanced, green, and efficient protocol for the synthesis of 1,8-dioxo-octahydroxanthenes and bis-5,5-dimethyl-1,3-cyclohexanediones by condensing aldo-nitrones (imine oxide) and dimedone (5,5-dimethyl-1,3-cyclohexanedione) under microwave irradiation is disclosed. Product formation (viz. xanthenes and bis-5,5-dimethyl-1,3-cyclohexanediones) is dependent on reaction conditions. The entire process is green and sustainable in terms of solvents, chemicals, reaction procedure, and yields. A plausible reaction mechanism of this reaction is also proposed. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for full experimental and spectral details.

  DOI：

  10.1080/00397911.2012.736584
• 作为产物：
  描述：

  α-(3-chloro)-N-phenylnitrone 、 5,5-二甲基-1,3-环己二酮 以 乙醇 为溶剂， 反应 1.5h， 以92%的产率得到2,2'-(3''-chlorophenyl)methylene-bis(5,5-dimethylcyclohexane-1,3-dione)
  参考文献：
  名称：

  Aldonitrones as Aldehyde Equivalents: An Efficient, Green, and Novel Protocol for the Synthesis of 1,8-Dioxo-octahydroxanthenes

  摘要：

  A novel, self-catalyzed, solvent-free, microwave-enhanced, green, and efficient protocol for the synthesis of 1,8-dioxo-octahydroxanthenes and bis-5,5-dimethyl-1,3-cyclohexanediones by condensing aldo-nitrones (imine oxide) and dimedone (5,5-dimethyl-1,3-cyclohexanedione) under microwave irradiation is disclosed. Product formation (viz. xanthenes and bis-5,5-dimethyl-1,3-cyclohexanediones) is dependent on reaction conditions. The entire process is green and sustainable in terms of solvents, chemicals, reaction procedure, and yields. A plausible reaction mechanism of this reaction is also proposed. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for full experimental and spectral details.

  DOI：

  10.1080/00397911.2012.736584

文献信息

• Tetraketones: A new class of tyrosinase inhibitors
  作者：Khalid Mohammed Khan、Ghulam Murtaza Maharvi、Mahmud Tareq Hassan Khan、Ahson Jabbar Shaikh、Shahnaz Perveen、Saeedan Begum、Mohammad Iqbal Choudhary

  DOI：10.1016/j.bmc.2005.08.029

  日期：2006.1

  Twenty-eight tetraketones (1-28) with variable substituents at C-7 were synthesized and evaluated as tyrosinase inhibitors. Remarkably compounds 25 (IC50 = 2.06 mu M), 11 (IC50 = 2.09 mu M), 15 (IC50 = 2.61 mu M), and 27 (IC50 = 3.19 mu M) were found to be the most active compounds of the series, even better than both standards kojic acid (IC50 = 16.67 mu M) and L-mimosine (IC50 = 3.68 mu M). This study may lead to the discovery of therapeutically potent agents against clinically very important dermatological disorders including hyperpigmentation as well as skin melanoma. (c) 2005 Elsevier Ltd. All rights reserved.
• Sekiya,M.; Suzuki,K., Chemical and pharmaceutical bulletin, 1971, vol. 19, p. 1540 - 1545
  作者：Sekiya,M.、Suzuki,K.

  DOI：——

  日期：——
• Aldonitrones as Aldehyde Equivalents: An Efficient, Green, and Novel Protocol for the Synthesis of 1,8-Dioxo-octahydroxanthenes
  作者：Dhruva Kumar、Suresh、Jagir S. Sandhu

  DOI：10.1080/00397911.2012.736584

  日期：2013.10.18

  A novel, self-catalyzed, solvent-free, microwave-enhanced, green, and efficient protocol for the synthesis of 1,8-dioxo-octahydroxanthenes and bis-5,5-dimethyl-1,3-cyclohexanediones by condensing aldo-nitrones (imine oxide) and dimedone (5,5-dimethyl-1,3-cyclohexanedione) under microwave irradiation is disclosed. Product formation (viz. xanthenes and bis-5,5-dimethyl-1,3-cyclohexanediones) is dependent on reaction conditions. The entire process is green and sustainable in terms of solvents, chemicals, reaction procedure, and yields. A plausible reaction mechanism of this reaction is also proposed. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for full experimental and spectral details.