2-(Diethylaminomethyl)cyclohexanon | 37408-85-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(Diethylaminomethyl)cyclohexanon
• 英文别名: 2-[(diethylamino)methyl]-cyclohexanone；2-(diethylaminomethyl)cyclohexan-1-one
• CAS: 37408-85-8
• 化学式: C₁₁H₂₁NO
• 分子量: 183.294
• InChiKey: LTBLMYLXXFMMIY-UHFFFAOYSA-N

物化性质

• 沸点：
  117 °C(Press: 24 Torr)
• 密度：
  0.929±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2922399090

反应信息

• 作为反应物：
  描述：

  2-(Diethylaminomethyl)cyclohexanon 在 乙醚 、 aluminium amalgam 作用下， 生成 2-diethylaminomethyl-cyclohexanol
  参考文献：
  名称：

  Matti, Bulletin de la Societe Chimique de France, 1932, vol. <4> 51, p. 974,976

  摘要：

  DOI：
• 作为产物：
  描述：

  环己酮 在 三乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 2-(Diethylaminomethyl)cyclohexanon
  参考文献：
  名称：

  A Convenient Regioselective Synthesis of Mannich Bases

  摘要：

  报道了一种新的、便捷的酮类化合物氨甲基化区域选择性过程，该过程涉及硅烷基烯醇醚和亚胺盐的现场生成。

  DOI：

  10.1055/s-1986-31742

文献信息

• Mechanistic studies on counter-ionic effects of camphorsulfonate-based ionic liquids on kinetics, thermodynamics and stereoselectivity of β-amino carbonyl compounds
  作者：Sabahat Sardar、Erum Jabeen、Cecilia Devi Wilfred、Ahmad Sazali Hamzah、Jean-Marc Leveque

  DOI：10.1016/j.molliq.2020.114370

  日期：2020.12

  Catalysis is important in various applications of organic chemistry and its output product control for stereoselective compounds is outrageous. Establishment of experimental facts of stereoselective compounds from catalysis and their validation using theoretical evidences is the key to understand various mechanisms of optically active compounds. A family of new ionic liquids (ILs) with various imidazolium

  催化作用在有机化学的各种应用中很重要，其对立体选择化合物的输出产物控制非常苛刻。通过催化作用建立立体选择性化合物的实验事实，并使用理论证据对其进行验证，是理解旋光化合物各种机理的关键。已经合成了具有各种咪唑鎓阳离子和樟脑磺酸根阴离子作为对环境有益的液态盐的一系列新型离子液体（IL），并将其用于催化β-氨基羰基化合物。使用IL作为均相催化剂形成产物，具有优异的产物收率和非对映选择性。根据反应动力学和产物收率，研究了抗衡离子，IL的哈米特酸度和粘度以及溶剂和温度的影响。密度泛函理论（DFT）用于研究反应机理的热力学研究。DFT计算预测，催化机理涉及IL的两个抗衡离子。此外，有证据表明，合成途径需要较低的活化能，而反途径产生热力学稳定的产物。这项研究探索了使用IL作为潜在的均相催化剂生产立体选择性物质的新途径。
• Carbon-Carbon Bond Formation by the Use of Chloroiodomethane as a C₁Unit. IV. The Mannich Reaction of Ketones by Means of Dihalomethane and Secondary Amine
  作者：Sotaro Miyano、Akira Mori、Hiroshi Hokari、Katsuaki Ohta、Harukichi Hashimoto

  DOI：10.1246/bcsj.55.1331

  日期：1982.4

  Treatment of ketones with dihalomethane (CH2Br2, CH2ClI, and CH2I2) in the presence of secondary amine, preferably pyrrolidine, gave the corresponding Mannich base in varing yields depending on the substrate and/or combination of the reagents.

  在仲胺（最好是吡咯烷）存在下，用二卤甲烷（CH2Br2、CH2ClI 和 CH2I2）处理酮类，根据底物和/或试剂组合的不同，可以得到相应的曼尼希碱，产率也不同。
• Reaction of nonstabilized azomethine ylides with Mannich bases: an approach to 3-acylpyrrolidines
  作者：Evgeniya V. Gorbunova、Evgeny M. Buev、Vladimir S. Moshkin、Vyacheslav Ya. Sosnovskikh

  DOI：10.1016/j.mencom.2019.03.008

  日期：2019.3

  Mannich bases obtained from cycloalkanones and methyl-ketones decompose on heating to give α,β-enones, which react in situ with nonstabilized azomethine ylides formed from spiro[anthracene-oxazolidines]. The final products, 3-acylpyrrolidines, were obtained in yields of 21–79% by heating the starting compounds in a microwave reactor in o-xylene at 210 °C for 45 min

  由环烷酮和甲基酮制得的曼尼希碱在加热时分解，得到α，β-烯酮，其与由螺[蒽-恶唑烷]形成的不稳定的偶氮甲亚胺原位反应。通过在微波反应器中于邻二甲苯中于210°C加热45分钟将起始化合物加热，可以得到最终产物3-酰基吡咯烷，产率为21–79％。
• Condensed diazepinones, their compositions and methods of use as
  申请人：Dr. Karl Thomae GmbH

  公开号：US04550107A1

  公开（公告）日：1985-10-29

  Disclosed are novel condensed diazepinones of formula I ##STR1## wherein B is a fused ring selected from ##STR2## X is --CH-- or, when B is ortho-phenylene, X can also be nitrogen; A.sub.1 is C.sub.1 -C.sub.2 alkylene; A.sub.2 is C.sub.1 -C.sub.2 when it is in the 2-position relative to the saturated heterocyclic ring nitrogen or a single bond or methylene when it is in the 3- or 4-position; R.sub.1 is C.sub.1 -C.sub.3 alkyl; R.sub.2 is C.sub.1 -C.sub.7 alkyl, optionally hydroxy-substituted on at least one of its second to seventh carbon, or C.sub.3 -C.sub.7 cycloalkyl, optionally hydroxy substituted, or C.sub.3 -C.sub.7 cycloalkylmethyl; or R.sub.1 and R.sub.2 can, together with the nitrogen therebetween, be a 4- to 7-membered saturated monocyclic, heterocyclic ring which can optionally include an oxygen or N--CH.sub.3 ; R.sub.3 is hydrogen, chlorine, or methyl; R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.5 is hydrogen, chlorine or C.sub.1 -C.sub.4 alkyl; and Z is a single bond, oxygen, methylene or 1,2-ethylene; and NR.sub.1 R.sub.2 --N oxides and nontoxic, pharmaceutically acceptable addition salts thereof. Also disclosed are pyrrolobenzodiazepinone intermediates, pharmaceutical compositions containing the condensed diazepinones and methods of using them to treat cardiovascular disorders, particularly bradycardia and bradyarrhythmia.

  本发明涉及一种新颖的公式I的紧凑二氮杂环酮，其中B是从以下中选择的融合环：##STR2## X是--CH--或者当B是邻苯二酚基时，X也可以是氮；A.sub.1是C.sub.1-C.sub.2烷基；A.sub.2是C.sub.1-C.sub.2，当它相对于饱和杂环环氮处于2位时，或者是单键或甲基烷基，当它位于3-或4-位时；R.sub.1是C.sub.1-C.sub.3烷基；R.sub.2是C.sub.1-C.sub.7烷基，在其第二至第七碳上可以选择性地取代羟基，或C.sub.3-C.sub.7环烷基，可以选择性地取代羟基，或C.sub.3-C.sub.7环烷基甲基；或者R.sub.1和R.sub.2可以与其中的氮一起，是4-至7-成员的饱和单环杂环，可以选择性地包括一个氧或N-CH.sub.3；R.sub.3是氢，氯或甲基；R.sub.4是氢或C.sub.1-C.sub.4烷基，R.sub.5是氢，氯或C.sub.1-C.sub.4烷基；和Z是单键，氧，亚甲基或1,2-乙烯基；以及NR.sub.1R.sub.2-N氧化物和无毒的、药学上可接受的加成盐。还公开了吡咯苯并二氮杂环酮中间体、含有紧凑二氮杂环酮的制药组合物以及使用它们治疗心血管疾病的方法，特别是缓慢心跳和缓慢心律不齐。
• 2'-Substituted-spiro(benzofuran-2(3H),1'-cycloalkanes), a process for preparing same, pharmaceutical compositions containing such compounds and their use as medicaments
  申请人：HOECHST-ROUSSEL PHARMACEUTICALS INCORPORATED

  公开号：EP0077536A2

  公开（公告）日：1983-04-27

  Compounds of the formula wherein X is hydrogen, halogen, amino, lower alkyl-substituted amino, hydroxy, lower alkyl, lower alkoxy, or nitro, m is an integer of 1, 2 or 3, X being the same or different when m is larger than 1, n is an integer of 0, 1 or 2, p is an integer of 0, 1 or 2, and R' and R2 are each independently hydrogen and lower alkyl, their preparation and their use as medicaments. Also intermediates of the formula wherein X, R1, R2, m, n and p are as defined above and Y is fluorine, chlorine or bromine.

  式中的化合物 其中 X 是氢、卤素、氨基、低级烷基取代的氨基、羟基、低级烷基、低级烷氧基或硝基，m 是 1、2 或 3 的整数，当 m 大于 1 时，X 相同或不同，n 是 0、1 或 2 的整数，p 是 0、1 或 2 的整数，R'和 R2 各自独立地为氢和低级烷基。此外，还有以下式子的中间体 其中 X、R1、R2、m、n 和 p 如上定义，Y 为氟、氯或溴。