9-(4,4-dimethyl-2-hydroxy-6-oxo-1-cyclohexenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroxanthene | 33742-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-(4,4-dimethyl-2-hydroxy-6-oxo-1-cyclohexenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroxanthene
• 英文别名: 9-(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)-3,3,6,6-tetramethyl-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione
• CAS: 33742-88-0
• 化学式: C₂₅H₃₂O₅
• 分子量: 412.526
• InChiKey: MNSNMKQVZCREDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-(4,4-dimethyl-2-hydroxy-6-oxo-1-cyclohexenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroxanthene 在 盐酸羟胺 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以91%的产率得到3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8-octahydroacridine-1,8-dione dioxime
  参考文献：
  名称：

  Synthesis and transformations of new 1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione derivatives

  摘要：

  Reactions of cyclohexane-1,3-diones with amines and aldehydes led to the formation of 1,21,3,4,5,16,7,8,9, 10-decahydroacridine-1,8-diones containing alkylaryl, aryl, and hydroxy substituents in position 10. Transformations of 10-hydroxy-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-diones under oxidation with nitrous acid, reduction with zinc powder, as well as on heating in aprotic solvents and acetic, phosphoric, and polyphosphoric acids, were studied. NMR spectra of 1,2,3,4,5,6,7,8,9,10-decaliydroacridine-1,8-diones having different substituents in positions 9 and 10 were analyzed.

  DOI：

  10.1134/s1070428008080198
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 原甲酸三乙酯 在 溶剂黄146 作用下， 以95%的产率得到9-(4,4-dimethyl-2-hydroxy-6-oxo-1-cyclohexenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroxanthene
  参考文献：
  名称：

  基于吡啶并[3,2-g]吲哚亚基的尿素衍生物受体的设计

  摘要：

  适当的 8-喹啉基腙的 Fischer 环化被用来制备一系列空腔形主体，该主体由一个中心吡啶环组成，由两个吡啶并 [3,2-g] 吲哚连接在 2,6-或 3,5-位。亚基。吡啶和吡啶并吲哚部分通过控制空腔形状的二亚甲基或三亚甲基桥进一步连接。具有二亚甲基桥的主体证明对氯仿或二氯甲烷溶液中的尿素衍生物有很强的亲和力。通过 NMR 滴定测量结合常数，并建立了涉及四个强氢键的结构结合模型。三亚甲基桥接主体的 X 射线分析揭示了一个空腔，该空腔太小而无法容纳尿素客体。

  DOI：

  10.1021/ja00056a008

文献信息

• Reactions of dimedone and alkyl orthoformates with and without activators
  作者：V. L. Novikov、V. P. Glazunov、N. N. Balaneva、O. P. Shestak

  DOI：10.1007/s11172-022-3652-6

  日期：2022.10

  The experimental and theoretical studies of the reactions of 5,5-dimethylcyclohexane-1,3-dione (dimedone) with trimethyl- and triethyl orthoformates under various conditions were carried out. It was demonstrated that in the absence of activators the reactions of substrate with ortho esters proceed exclusively as C-C coupling, and in the presence of Brønsted (H2SO4) or Lewis (BF3·Et2O) acids the formation of both C-C and C-O coupling products is observed. The energy consumptions of all reactions in accordance with proposed mechanisms were estimated using quantum chemical calculations by the B3LYP/6-311++G(d,p) method in terms of PCM/MeCN.

  对5,5-二甲基环己烷-1,3-二酮（二甲酮）与原甲酸三甲酯和原甲酸三乙酯在各种条件下的反应进行了实验和理论研究。结果表明，在没有活化剂的情况下，底物与原酯的反应仅以C-C偶联的方式进行，而在有布伦斯特（H2SO4）或路易斯（BF3·Et2O）酸的情况下，观察到C-C和C-O偶联产物的形成。根据所提出的机制，使用B3LYP/6-311++G（d，p）方法，以PCM/MeCN为条件，通过量子化学计算对所有反应的能量消耗进行了估算。
• Kocevar, Marijan; Polanc, Slovenko; Vercek, Bojan, Liebigs Annalen der Chemie, 1990, # 5, p. 501 - 503
  作者：Kocevar, Marijan、Polanc, Slovenko、Vercek, Bojan、Tisler, Miha

  DOI：——

  日期：——
• Zur Kinetik der Bildung von Arylaminomethylenverbindungen aus Triethoxymethan, Arylaminen und CH2-aciden Verbindungen in einer Dreikomponentenkondensation
  作者：Georg Uray、Otto S. Wolfbeis

  DOI：10.1007/bf00899677

  日期：1981.5
• KOCEVAR, MARIJAN;POLANC, SLOVENKO;VERCEK, BOJAN;TISLER, MIHA, LIEBIGS ANN. CHEM.,(1990) N, C. 501-503
  作者：KOCEVAR, MARIJAN、POLANC, SLOVENKO、VERCEK, BOJAN、TISLER, MIHA

  DOI：——

  日期：——
• Synthesis and transformations of new 1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione derivatives
  作者：A. N. Pyrko

  DOI：10.1134/s1070428008080198

  日期：2008.8

  Reactions of cyclohexane-1,3-diones with amines and aldehydes led to the formation of 1,21,3,4,5,16,7,8,9, 10-decahydroacridine-1,8-diones containing alkylaryl, aryl, and hydroxy substituents in position 10. Transformations of 10-hydroxy-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-diones under oxidation with nitrous acid, reduction with zinc powder, as well as on heating in aprotic solvents and acetic, phosphoric, and polyphosphoric acids, were studied. NMR spectra of 1,2,3,4,5,6,7,8,9,10-decaliydroacridine-1,8-diones having different substituents in positions 9 and 10 were analyzed.