1,3,3,7,9-pentamethyl-2-azaspiro[4.5]deca-1,6,9-trien-8-one | 1361927-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 1,3,3,7,9-pentamethyl-2-azaspiro[4.5]deca-1,6,9-trien-8-one
• CAS: 1361927-95-8
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: CMGXMIHLDGDXDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3,3,7,9-pentamethyl-2-azaspiro[4.5]deca-1,6,9-trien-8-one 、 3-(4-bromobenzoyl)pyrrolo[1,2-a]quinoxaline-1,2,4(5H)-trione 以 乙腈 为溶剂， 反应 0.33h， 以94%的产率得到3-(4-bromobenzoyl)-2-hydroxy-3-{(3,3,7,9-tetramethyl-8-oxo-2-azaspiro[4.5]deca-1,6,9-trien-1-yl)methyl}pyrrolo[1,2-a]quinoxaline-1,4(3aH,5H)-dione
  参考文献：
  名称：

  Five-membered 2,3-dioxoheterocycles: XCVI. Reactions of 3-aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5h)-triones with substituted 1,3,3-trimethyl-2-azaspiro[4.5]dec-1-enes

  摘要：

  3-Aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones react with 1,3,3,7,9-pentamethyl-2-azaspiro-[4.5] deca-1,6,9-trien-8-one and 2',5',5'-trimethyl-4',5'-dihydro-4H-spiro[naphthalene-1,3'-pyrrol]-4-one providing 3-aroyl-2-hydroxy-3a-{(3,3,7,9-tetramethyl-8-oxo-2-azaspiro[4.5]deca-1,6,9-trien-1-yl)methyl}pyrrolo[1,2-a-quinoxaline-1,4(3a H,5H)-diones and 3-aroyl-2-hydroxy-3a-{(5',5'-dimethyl-4-oxo-4',5'-dihydro-4H-spiro[naphthalene-1,3'-pyrrol]-2'-yl)methyl}pyrrolo[1,2-a]-quinoxaline-1,4(3aH,5H)-diones.

  DOI：

  10.1134/s1070428013110171
• 作为产物：
  描述：

  2,6-二甲基大茴香醚 在 aluminum (III) chloride 、 sodium tetrahydroborate 、 硫酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 2.33h， 生成 1,3,3,7,9-pentamethyl-2-azaspiro[4.5]deca-1,6,9-trien-8-one 、 7-methoxy-1,3,3,6,8-pentamethyl-3,4-dihydroisoquinoline
  参考文献：
  名称：

  Ritter reaction. Synthesis of 1-substituted 3,3,7,9-tetramethyl-2-azaspiro[4.5]deca-6,9-dien- and -1,6,9-trien-8-ones and 7-methoxy-3,3,6,8-tetramethyl-3,4-dihydroisoquinolines

  摘要：

  1-(4-Methoxy-3,5-dimethylphenyl)-2-methylpropan-1-ol reacted with nitriles [MeSCN, PhCN, MeCN, EtOC(O)CH2CN] in the presence of concentrated sulfuric acid to give both 1-R-3,3,7,9-tetramethyl-2-azaspiro[4,5]deca-6,9-dien- and -1,6,9-trien-8-ones and 1-R-7-methoxy-3,3,6,8-tetramethyl-3,4-dihydroisoquinolines. The reaction with 3,4-dimethoxyphenylacetonitrile afforded 10,11-dimethoxy-1,3,6,6-tetramethyl-1,5,6,12b-tetrahydrodibenzo[d,f]indole-2,8-dione. Three-component condensation of 2-methoxy-1,3-dimethylbenzene with isobutyraldehyde and nitriles led to the formation of spirocyclic systems and 3,4-dihydroisoquinoline derivatives in lower yield.

  DOI：

  10.1134/s1070428013070166

文献信息

• Synthesis of 1-substituted 2-azaspiro[4.5]deca-6,9-dien-8-ones and 2-azaspiro[4.5]deca-1,6,9-trien-8-ones by condensation of 2,6-dimethylphenol with isobutyraldehyde and nitriles
  作者：Yu. S. Rozhkova、K. A. Khmelevskaya、Yu. V. Shklyaev、M. A. Ezhikova、M. I. Kodess

  DOI：10.1134/s1070428012010101

  日期：2012.1

  1-Substituted 3,3,7,9-tetramethyl-2-azaspiro[4.5]deca-6,9-dien-8-ones and 3,3,7,9-tetramethyl-2azaspiro[4.5]deca-1,6,9-trien-8-ones were synthesized by three-component condensation of 2,6-dimethylphenol with isobutyraldehyde and nitriles in concentrated sulfuric acid.
• Acylation of the enamino tautomer of 2-azaspiro[4.5]deca-1,6,9-trien-8-ones with 5-arylfuran-2,3-diones. Crystal and molecular structure of (2Z,5Z)-3-Hydroxy-5-(6,9-dimethoxy-3,3-dimethyl-8-oxo-2-azaspiro[4.5]deca-6,9-dien-1-ylidene)-1-phenylpent-2-ene-1,4-dione
  作者：V. V. Konovalova、Yu. S. Rozhkova、Yu. V. Shklyaev、P. A. Slepukhin、A. N. Maslivets

  DOI：10.1134/s1070428014120112

  日期：2014.12

  5-Arylfuran-2,3-diones reacted with heterocyclic enamines of the 2-azaspiro[4.5]deca-1,6,9-trien-8-one series to give products of beta-CH-acylation of the enamino fragment. The structure of (2Z,5Z)-3-hydroxy-5-(6,9-dimethoxy-3,3-dimethyl-8-oxo-2-azaspiro[4.5]deca-6,9-dien-1-ylidene)-1-phenylpent-2-ene-1,4-dione was proved by X ray analysis.