2,2,5-trimethylcycloheptane-1,3-dione | 33766-38-0

• 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: 2,2,5-trimethylcycloheptane-1,3-dione
• 英文别名: (5R)-2,2,5-trimethylcycloheptane-1,3-dione
• CAS: 33766-38-0
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: AVRZKVUQKXUOQG-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,5-trimethylcycloheptane-1,3-dione 、 2-氨基苯甲腈 在 三氟化硼乙醚 、 水 、 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以78%的产率得到(9R)-11-amino-6,6,9-trimethyl-9,10-dihydro-6H-cyclohepta[b]quinolin-7(8H)-one
  参考文献：
  名称：

  Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones

  摘要：

  This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF3 center dot Et2O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure-activity relationship some trends are suggested. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.039
• 作为产物：
  描述：

  (R)-胡薄荷酮氧化物 在 三氟化硼乙醚 作用下， 以90%的产率得到2,2,5-trimethylcycloheptane-1,3-dione
  参考文献：
  名称：

  Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones

  摘要：

  This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF3 center dot Et2O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure-activity relationship some trends are suggested. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.039

文献信息

• Solid-Acid Catalysed Rearrangement of Cyclic α,β-Epoxy Ketones
  作者：Jacob A. Elings、Hans E. B. Lempers、Roger A. Sheldon

  DOI：10.1002/(sici)1099-0690(200005)2000:10<1905::aid-ejoc1905>3.0.co;2-o

  日期：2000.5

  Various cyclic α,β-epoxy ketones rearranged to α-formyl ketones and/or vic-diones in the presence of catalytic amounts of zeolites and montmorillonite K10. This provides an excellent alternative to conventional homogeneous systems with respect to yields and workup. Differences in product distribution and type of products in the rearrangement of pulegone oxide could be reasonably explained by invoking

  在催化量的沸石和蒙脱石 K10 存在下，各种环状 α,β-环氧酮重排为 α-甲酰基酮和/或维克二酮。就产量和后处理而言，这为传统均相系统提供了极好的替代方案。通过调用均相和非均相催化剂的不同途径，可以合理地解释胡薄荷酮重排过程中产物分布和产物类型的差异。
• The Zinc Bromide-catalyzed Rearrangement of Pulegone Oxide and Piperitone Oxide
  作者：Hajime Watanabe、Jun Katsuhara、Noriyuki Yamamoto

  DOI：10.1246/bcsj.44.1328

  日期：1971.5

  The rearrangement of (+)-cis- (I) and (−)-trans-pulegone oxide (II) was effected by the catalysis of zinc bromide in boiling benzene to give the same (−)-2,2,5-trimethylcyclohepta-1,3-dione (III), with a retention of the optical activity. The structure of (−)-III with the expanded 7-membered ring was confirmed by the chemical transformation into 1,1,4-trimethyl-cycloheptane(IV), which was identical

  (+)-cis- (I) 和 (-)-trans-pulegone oxide (II) 的重排是通过溴化锌在沸腾苯中的催化作用得到相同的 (-)-2,2,5-trimethylcyclohepta -1,3-二酮 (III)，保留了旋光性。通过化学转化为 1,1,4-三甲基-环庚烷 (IV) 证实了 (-)-III 具有扩展的 7 元环的结构，这与衍生自丁香酮 (V) 的相同。胡椒酮氧化物 (VIII) 也以与胡薄荷酮氧化物相同的方式转化为二酚 (X)。
• On the geometric requirements for concerted 1,2-carbonyl migration in α,β-epoxy ketones
  作者：Robert D. Bach、Russell C. Klix

  DOI：10.1016/s0040-4039(00)98492-2

  日期：1985.1

  The stabilizing influence of neighboring group participation by the carbonyl group in concerted 1,2-acyl migration is related to the ability of the molecule to assume a transition stage geometry resembling a cyclopropyloxenium ion.

  在协同的1，2-酰基迁移中，羰基对邻近基团参与的稳定影响与分子具有类似于环丙基氧鎓离子的过渡阶段几何形状的能力有关。
• BACH, R. D.;KLIX, R. C., TETRAHEDRON LETT., 1985, 26, N 8, 985-988
  作者：BACH, R. D.、KLIX, R. C.

  DOI：——

  日期：——
• Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones
  作者：Diego dos Santos Pisoni、Jessie Sobieski da Costa、Douglas Gamba、Cesar Liberato Petzhold、Antonio César de Amorim Borges、Marco Antonio Ceschi、Paula Lunardi、Carlos Alberto Saraiva Gonçalves

  DOI：10.1016/j.ejmech.2009.10.039

  日期：2010.2

  This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF3 center dot Et2O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure-activity relationship some trends are suggested. (C) 2009 Elsevier Masson SAS. All rights reserved.