3-Allylamino-5,5-dimethyl-2-cyclohexen-1-on | 55800-10-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Allylamino-5,5-dimethyl-2-cyclohexen-1-on
• 英文别名: 5,5-Dimethyl-3-(prop-2-enylamino)cyclohex-2-en-1-one
• CAS: 55800-10-7
• 化学式: C₁₁H₁₇NO
• mdl: MFCD00466837
• 分子量: 179.262
• InChiKey: KOBVUUCCHKEBRP-UHFFFAOYSA-N

物化性质

• 熔点：
  75-75.5 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  271.5±40.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.545
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Allylamino-5,5-dimethyl-2-cyclohexen-1-on 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61%的产率得到3-Allylamino-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
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 丙烯胺 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.47h， 以81%的产率得到3-Allylamino-5,5-dimethyl-2-cyclohexen-1-on
  参考文献：
  名称：

  Paira; Misra; Roy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 6, p. 966 - 969

  摘要：

  DOI：

文献信息

• One-pot, three-component synthesis of spiro[indeno[1,2-b]quinoline-10,3′-pyrroles] via the Hantzsch-type reaction of 1H-pyrrole-2,3-diones
  作者：Maksim V. Dmitriev、Tatyana V. Salnikova、Pavel S. Silaichev、Andrey N. Maslivets

  DOI：10.1016/j.tetlet.2016.11.100

  日期：2017.1

  A new methodology for the synthesis of spiro[indeno[1,2-b]quinoline-10,3′-pyrrole] derivatives via a Hantzsch-type reaction has been developed. This process involves the one-pot, three-component reaction of a 1H-pyrrole-2,3-dione, an aminocyclohexenone and 1,3-indanedione in acetic acid at reflux. Operationally simple, metal-free reaction conditions, simplicity of product isolation and good yields

  通过Hantzsch型反应合成螺[茚并[1,2 - b ]喹啉-10,3'-吡咯]衍生物的新方法已经开发出来。该过程涉及1 H-吡咯-2，3-二酮，氨基环己烯酮和1，3-茚满二酮在乙酸中的一锅三组分反应。操作简单，无金属的反应条件，产物分离的简单性和良好的收率是该方法的关键优势。
• Five-membered 2,3-dioxo heterocycles: XLIX. Reaction of methyl 1-aryl-3-aroyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates with N-substituted 3-amino-5,5-dimethyl-2-cyclohexenones
  作者：Yu. N. Bannikova、A. N. Maslivets、Z. G. Aliev

  DOI：10.1007/s11178-005-0101-6

  日期：2004.12

  Methyl 1-aryl-3-aroyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates react with N-substituted 3-amino-5,5-dimethyl-2-cyclohexenones to give 4′-hydroxy-1′-aryl-3′-aroyl-6,6-dimethyl-1′, 2,3,4,5,5′,6,7-octahydro-1H,2′H-indole-3-spiro-2′-pyrrole-2,4,5′-triones. The structure of the products was proved by the X-ray diffraction data for the 1-cyclohexyl derivative.

  1-aryl-3-aroyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates 与 N-取代的 3-amino-5、5-二甲基-2-环己烯酮反应，得到 4′-羟基-1′-芳基-3′-芳酰基-6,6-二甲基-1′, 2,3,4,5,5′,6,7-octahydro-1H,2′H-indole-3-spiro-2′-pyrrole-2,4,5′-triions.1-cyclohexyl 衍生物的 X 射线衍射数据证明了产品的结构。
• Five-membred 2,3-dioxoheterocycles: LXXXI. Reactions of 4,5-bis(methoxycarbonyl)-1H-pyrrole-2,3-diones with N-substituted 3-amino-5,5-dimethyl-2-cyclohex-2-en-1-ones. crystal and molecular structure of methyl 4′-hydroxy-6,6-dimethyl-1,1′-bis(4-methylphenyl)-2,4,5′-trioxo-1,1′,2,4,5,5′,6,7-octahydrospiro[indole-3,2′-pyrrole]-3′-carboxylate
  作者：P. S. Silaichev、M. A. Chudinova、P. A. Slepukhin、A. N. Maslivets

  DOI：10.1134/s107042801111011x

  日期：2011.11

  1-Aryl-4,5-bis(methoxycarbonyl)-1H-pyrrole-2,3-diones react with N-substituted 3-amino-5,5-dimethylcyclohex-2-en-1-ones affording methyl 1,1'-diaryl-4'-hydroxy-6,6-dimethyl-2,4,5'-trioxo-1,1',2,4,5,5',6,7-octahydrospiro[indole-3,2'-pyrrole]-3'-carboxylates whose structure was proved by XRD analysis.
• Five-membered 2,3-dioxo heterocycles: LXIII. Cascade recyclization of isopropyl 2-(1-aryl-4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrol-3-yl)-2-oxoacetates with cyclic enamines. Crystalline and molecular structure of 1′-benzyl-6′,6′-dimethyl-3-[(Z)-phenyl(phenylamino)methylidene]-6′,7′-dihydro-3H-spiro[furan-2,3′-indole]-2′,4,4′,5(1′H,5′H)-tetraone
  作者：P. S. Silaichev、Z. G. Aliev、A. N. Maslivets

  DOI：10.1134/s1070428009010163

  日期：2009.1

  Isopropyl 2-(1-aryl-4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrol-3-yl)-2-oxoacetates reacted with N-substituted 3-amino-5,5-dimethylcyclohex-2-en-1-ones to give the corresponding 1'-substituted (Z)-6',6'-dimethyl-3-[phenyl(arylamino)methylidene]-6',7'-dihydro-3H-spiro[furan-2,3'-indole]-2',4,4',5(1'H,5'H)-tetraones. The structure of 1'-benzyl-6',6'-dimethyl-3-[(Z)-phenyl(phenylamino)methylidene]-6',7'-dihydro-3Hspiro[furan-2,3'-indole]-2',4,4',5(1'H,5'H)-tetraone was proved by X-ray analysis.
• Five-membered 2,3-dioxo heterocycles: LI. Reaction of 3-aroyl-2,4-dihydro-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones with 3-amino-5,5-dimethylcyclohex-2-en-1-ones
  作者：N. L. Racheva、S. N. Shurov、Z. G. Aliev、A. N. Maslivets

  DOI：10.1134/s1070428007010149

  日期：2007.1

  3-Aroyl-2,4-dihydro-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones react with N-unsubstituted and N-substituted 3-amino-5,5-dimethylcyclohex-2-en-1-ones to give 3'-aroyl-4'-hydroxy-1'-(o-hydroxy-phenyl)-6,6-dimethyl-6,7-dihydrospiro[indole-3,2'-pyrrole]-2,4,5'(1H,1'H,5H)-triones. The molecular and crystalline structure of the 1-cyclohexyl-substituted derivative was studied by X-ray analysis.