3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)(pyridin-3-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one

• 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: 3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)(pyridin-3-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one
• 英文别名: 2,2'-(pyridin-3-ylmethylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone)；3-Hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)-pyridin-3-ylmethyl]-5,5-dimethylcyclohex-2-en-1-one
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: GYRNBUVBFWSCNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)(pyridin-3-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 0.17h， 生成 3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(pyridin-3-yl)-2H-xanthene-1,8(5H,9H)-dione
  参考文献：
  名称：

  Transition metal and base free coupling of N-tosylhydrazones with 1,3-dicarbonyl compound

  摘要：

  N-tosylhydrazones derived from a wide variety of aryl, alkyl and heteroaryl aldehydes undergo smooth coupling with 5,5-dimethylcyclohexane-1,3-dione under transition metal and base free conditions to generate tetraketo compounds in high yields. In presence of a base, the coupling reaction generates beta-keto enol ether as the major product in a polar aprotic solvent. N-Tosylhydrazone can also be converted to xanthenedione in high yields in one-pot operation under mild acidic conditions. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.02.001
• 作为产物：
  描述：

  2,2'-((4-methoxyphenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) 在 zinc(II) chloride 作用下， 以 水 为溶剂， 反应 3.5h， 生成 3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)(pyridin-3-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one
  参考文献：
  名称：

  Zinc Chloride Catalyzed Collective Synthesis of Arylmethylene Bis(3- hydroxy-2-cyclohexene-1-ones) and 1,8-Dioxo-octahydroxanthene/acridine Derivatives

  摘要：

  催化量的 ZnCl2 在室温下有效促进了水相中芳基亚甲基双(3-羟基-2-环己烯-1-酮)的快速合成，所得产率优异。在升高温度下，ZnCl2 还催化了一锅法合成 1,8-二氧代-八氢萘和 1,8-二氧代-十氢氟啶类化合物，产率良好。在特定情况下，反应介质中观察到芳基亚甲基双(3-羟基-2-环己烯-1-酮)中二美烯的不寻常解离。通过向反应混合物中添加已知过量的二美烯，可以将其最小化或避免，在 1,8-二氧代-八氢萘的一锅法合成中。

  DOI：

  10.2174/1570178611666140612211155

文献信息

• Multicomponent Synthesis of Functionalized Tetrahydroacridinones: Insights into a Mechanistic Route
  作者：Tsai-Wen Chung、Bharat D. Narhe、Chun-Cheng Lin、Chung-Ming Sun

  DOI：10.1021/acs.orglett.5b02705

  日期：2015.11.6

  of three-component reactions of various aromatic amines with a number of aldehydes and 1,3-diones was achieved. The unprecedented reaction involved a nucleophilic attack of an aromatic amine on the in situ generated Michael adduct intermediate followed by six-electron ring cyclizations. It is contrary to the common belief that advocates involvement of coupling reactions between a Knoevenagel adduct

  进行了各种芳香胺与许多醛和1,3-二酮的三组分反应的机理研究。前所未有的反应涉及芳香胺对原位生成的迈克尔加合物中间体的亲核攻击，然后进行六电子环环化。与提倡在Knoevenagel加合物和芳族胺之间进行偶联反应以传递取代的四氢ac啶酮的普遍信念相反。
• Transition metal and base free coupling of N-tosylhydrazones with 1,3-dicarbonyl compound
  作者：Deepika Choudhary、Chanchal Agrawal、Vineeta Khatri、Ranjit Thakuria、Ashok K. Basak

  DOI：10.1016/j.tetlet.2017.02.001

  日期：2017.3

  N-tosylhydrazones derived from a wide variety of aryl, alkyl and heteroaryl aldehydes undergo smooth coupling with 5,5-dimethylcyclohexane-1,3-dione under transition metal and base free conditions to generate tetraketo compounds in high yields. In presence of a base, the coupling reaction generates beta-keto enol ether as the major product in a polar aprotic solvent. N-Tosylhydrazone can also be converted to xanthenedione in high yields in one-pot operation under mild acidic conditions. (C) 2017 Elsevier Ltd. All rights reserved.
• Zinc Chloride Catalyzed Collective Synthesis of Arylmethylene Bis(3- hydroxy-2-cyclohexene-1-ones) and 1,8-Dioxo-octahydroxanthene/acridine Derivatives
  作者：Subramaniapillai Ganesan、Jagatheeswaran Kothandapani、Asaithampi Ganesan

  DOI：10.2174/1570178611666140612211155

  日期：2014.9

  Catalytic amount of ZnCl2 efficiently promoted rapid synthesis of arylmethylene bis(3-hydroxy-2-cyclohexene- 1-one) in water at room temperature in excellent yield. At elevated temperature, ZnCl2 also catalyzed one-pot synthesis of 1,8-dioxo-octahydroxanthene and 1,8-dioxo-decahydroacridine derivatives in good yield. In specific instances, unusual dissociation of dimedone from the arylmethylene bis(3-hydroxy-2-cyclohexene-1-one) was identified in the reaction medium. It was minimized/avoided by the addition of known excess dimedone to the reaction mixture in the one-pot synthesis of 1,8-dioxo-octahydroxanthene

  催化量的 ZnCl2 在室温下有效促进了水相中芳基亚甲基双(3-羟基-2-环己烯-1-酮)的快速合成，所得产率优异。在升高温度下，ZnCl2 还催化了一锅法合成 1,8-二氧代-八氢萘和 1,8-二氧代-十氢氟啶类化合物，产率良好。在特定情况下，反应介质中观察到芳基亚甲基双(3-羟基-2-环己烯-1-酮)中二美烯的不寻常解离。通过向反应混合物中添加已知过量的二美烯，可以将其最小化或避免，在 1,8-二氧代-八氢萘的一锅法合成中。