3-Amino-2-bromo-5,5-dimethyl-cyclohex-2-enone | 51924-68-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Amino-2-bromo-5,5-dimethyl-cyclohex-2-enone
• 英文别名: 3-Amino-2-bromo-5,5-dimethylcyclohex-2-en-1-one
• CAS: 51924-68-6
• 化学式: C₈H₁₂BrNO
• 分子量: 218.093
• InChiKey: OSZBFYXZPCAKFN-UHFFFAOYSA-N

物化性质

• 沸点：
  248.980±40.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.429±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Amino-2-bromo-5,5-dimethyl-cyclohex-2-enone 、 4-Isopropylamino-5-amino-6-mercaptopyrimidin 以51%的产率得到
  参考文献：
  名称：

  Synthesis and pharmacological properties of 4,9-diamino derivatives of 7,8-dihydro-1,3-diazaphenothiazine

  摘要：

  DOI：

  10.1007/bf00767831
• 作为产物：
  描述：

  3-氨基-5,5-二甲基-2-环己烯-1-酮 在 N-溴代丁二酰亚胺(NBS) 、 monmorillonite K-10 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以60%的产率得到3-Amino-2-bromo-5,5-dimethyl-cyclohex-2-enone
  参考文献：
  名称：

  α-Bromination of β-Enamino Compounds Using K-10

  摘要：

  使用蒙脱石（K-10）支撑的 NBS 方便地制备了一系列δ-溴 3-氨基-5,5-二甲基环己-2-烯-1-酮 2a-g 和δ-溴 ²-烯氨基化合物 4a, b。对于 3-氨基-5,5-二甲基环己-2-烯-1-酮 1b、e、g，还研究了其他反应条件，如二叔丁基过氧化物/NBS/CCl4 和 Br2/CH2Cl2，结果制备出了单溴和双溴化合物混合物 5b、f、g 和 6b、e、g。

  DOI：

  10.1055/s-2001-17702

文献信息

• Studies on Enaminoketones
  作者：Ivo Jirkovsky

  DOI：10.1139/v74-009

  日期：1974.1.1

  A series of N-substituted 3-amino-2-cyclohexen-1-ones and 3-amino-5,5-dimethyl-2-cyclohexen-1-ones (1–9) has been prepared. Halogenation of these compounds with bromine, NBS, cyanogen bromide, and iodine is described. The tendency of enaminoketones to form salts of the corresponding enol-ketimine form was observed and structures of the salts are supported by their p.m.r. and i.r. properties. The reaction of 3-benzylamino-2-bromo-5,5-dimethyl-2-cyclohexen-1-one with concentrated sulfuric acid effected debenzylation. Treatment of 3-benzylamino-2-iodo-5,5-dimethyl-2-cyclohexen-1-one with dibenzoyl peroxide gave 8,8a-dihydro-5-iodo-8,8-dimethyl-2,3-diphenyl-4H-1,4-benzoxazine-6,7-diol. The above secondary enaminoketones 1–9 were shown to react with phenyl isocyanates, phenyl isothiocyanate. and methyl isothiocyanate under fusion conditions to yield substituted 2-amino-6-oxo-1-cyclo-hexene-1-carboxamides and corresponding thiocarboxamides. 2-Benzylamino-6-oxo-N-phenyl-1-cyclohexene-1-carboxamide and its 5,5-dimethyl analog were found to undergo facile transamination in position 2, when heated with a primary amine. This reaction is of synthetic utility for the preparation of biologically active derivatives with a basically substituted side chain. Addition of 4-methylamino-3-pentene-2-one to phenyl isocyanate afforded 2-acetyl-3-methylaminoisocrotonanilide; the spectroscopic properties of this product are discussed.

  已准备了一系列N-取代的3-氨基-2-环己烯-1-酮和3-氨基-5,5-二甲基-2-环己烯-1-酮（1-9）。描述了这些化合物与溴、NBS、溴化氰和碘的卤化反应。观察到烯胺酮形成相应烯醇-酮亚胺形式的盐的倾向，并通过它们的p.m.r.和i.r.性质支持盐的结构。3-苄基氨基-2-溴-5,5-二甲基-2-环己烯-1-酮与浓硫酸反应发生了去苄基化。3-苄基氨基-2-碘-5,5-二甲基-2-环己烯-1-酮与二苯甲酰过氧化物处理形成了8,8a-二氢-5-碘-8,8-二甲基-2,3-二苯基-4H-1,4-苯并噁嗪-6,7-二醇。上述二级烯胺酮1-9被证明在熔融条件下与苯基异氰酸酯、苯基异硫氰酸酯和异硫氰酸甲酯发生反应，生成取代的2-氨基-6-氧代-1-环己烯-1-羧酰胺和相应的硫羧酰胺。发现2-苄基氨基-6-氧代-N-苯基-1-环己烯-1-羧酰胺及其5,5-二甲基类似物在与一级胺加热时在2位轻松进行转氨化。这种反应对于制备具有基本取代侧链的生物活性衍生物具有合成实用性。将4-甲基氨基-3-戊烯-2-酮加入苯基异氰酸酯生成了2-乙酰基-3-甲基氨基异丁烯酰胺；讨论了该产物的光谱性质。
• Process for producing cyclohexane-1,3-diones or 3-alkoxy-2-cyclohexenones
  申请人：MITSUI PETROCHEMICAL INDUSTRIES, LTD.

  公开号：EP0003738A1

  公开（公告）日：1979-09-05

  3-aminocyclohexene-2-one-1 is prepared by heating 5-oxohexanenitrile of the formula and cyclohexane-1.3-diones and 3-alkoxycyclohexene-2- ones-1 are prepared by reacting a 3-aminocyclohexene-2- one-1 of the formula wherein R represents amino or alkylamino, R3 represents a non-reactive substituent, and n is 0, 1 or 2, with water or a monohydric or dihydric alcohol of 1 to 10 carbon atoms. The process provides the desired compounds, useful as intermediates in the preparation of medicines, agricultural chemicals, perfumes and resin substitutes, in good yields from readily available and inexpensive starting materials.

  3-氨基环己烯-2-酮-1 是通过加热式 5-氧代己腈和环己烷-1.3-二酮以及 3-烷氧基环己烯-2-酮-1 而制备的。 和环己烷-1.3-二酮和 3-烷氧基环己烯-2-酮-1 是由式 3-氨基环己烯-2-酮-1 反应制备的。 其中 R 代表氨基或烷基氨基，R3 代表非反应性取代基，n 为 0、1 或 2，与水或 1 至 10 个碳原子的一元醇或二元醇反应。 该工艺提供了所需的化合物，可用作制备药物、农药、香水和树脂替代品的中间体，且起始原料容易获得，价格低廉，收率高。
• NEMERYUK, M. P.;TOLOKONTSEVA, L. A.;PYXOVA, M. V.;POLEZHAEVA, A. I.;ROSHC+, XIM.-FARMATS. ZH., 1985, 19, N 8, 964-968
  作者：NEMERYUK, M. P.、TOLOKONTSEVA, L. A.、PYXOVA, M. V.、POLEZHAEVA, A. I.、ROSHC+

  DOI：——

  日期：——
• CHIMERIC GABAB RECEPTOR
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP1664112A2

  公开（公告）日：2006-06-07
• Chimeric gaba receptor
  申请人：Smans Astrid Karine Alfonsine

  公开号：US20060216749A1

  公开（公告）日：2006-09-28

  The present invention provides an isolated GABA B receptor protein comprising at least one GABA B R1 a subunit and at least one GABA B R2 a subunit, characterized in that said GABA B receptor has one high affinity agonist binding site and one low affinity agonist binding site. In particular the isolated recombinant GABA B receptor protein expressed by the hGABA B R1 a /GABA B R2 CHO cell line deposited at the Belgian Coordinated Collections of Microorganisms (BCCM) as CHO-K1 h-GABA-b R1 a /R2 clone on Aug. 22, 2003 with the accession number LMBP 6046CB. It is thus an object of the present invention to provide the hGABA B R1 a /GABA B R2 CHO cell line deposited at the Belgian Coordinated Collections of Microorganisms (BCCM) as CHO-K1 h-GABA-b R1 a /R2 clone on Aug. 22, 2003 with the accession number LMBP 6046CB. The invention also provides the use of the aforementioned cell line in a method to identify GABA B receptor agonists using a functional or a binding assay. In particular in a radioligand-binding assay comprising the use of radiolabeled agonists such as for example 3 H-GABA or 3 H-baclofen. In a particular embodiment the present invention provides the use of the aforementioned GABA B receptor in a method to identify a high affinity GABA B receptor agonist using a functional or a binding assay. In particular in a radioligand-binding assay comprising the use of radiolabeled agonists such as for example 3 H-GABA or 3 H-baclofen. Alternatively, the aforementioned binding assays are performed on cellular extracts, in particular cellular membrane preparations of the aforementioned cells.