2',5',5'-trimethyl-4',5'-dihydro-4H-spiro[naphthalene-1,3'-pyrrol]-4-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2',5',5'-trimethyl-4',5'-dihydro-4H-spiro[naphthalene-1,3'-pyrrol]-4-one
• 英文别名: 2,2,5-trimethylspiro[3H-pyrrole-4,4'-naphthalene]-1'-one
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: BKVKFSRJXJXPPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  4-benzoyl-5-phenyl-furan-2,3-dione 、 2',5',5'-trimethyl-4',5'-dihydro-4H-spiro[naphthalene-1,3'-pyrrol]-4-one 以 苯 为溶剂， 反应 1.0h， 以89%的产率得到(Z)-3-benzoyl-5-(5',5'-dimethyl-4-oxo-4-spiro[naphthalene-1,3'-pyrrolidin]-2'-ylidene)-4-phenylcyclopent-3-ene-1,2-dione
  参考文献：
  名称：

  Five-Membered 2,3-dioxoheterocycles: XCV. Recyclization of 4-benzoyl-5-phenylfuran-2,3-dione at the action of substituted 1,3,3-trimethyl-2-azaspiro[4.5]dec-1-enes. Crystal and molecular structure of substituted 5-(2-azaspiro[4.5]dec-1-ylidene)cyclopent-3-ene-1,2-dione

  摘要：

  4-Benzoyl-5-phenylfuran-2,3-dione reacts with 2',5',5'-trimethyl-4',5'-dihydro-4H-spiro[naphthalene-1,3'-pyrrol]-4-one and 8-(2-methoxy-5-methylphenyl)-1,3,3,9-tetramethyl-2-azaspiro[4.5]deca-1,7-dien-6-one with the formation of (Z)-3-benzoyl-5-(5',5'-dimethyl-4-oxo-4H-spiro[naphthalene-1,3'-pyrrolidin]-2'-ylidene)-4-phenylcyclopent-3-ene-1,2-dione, whose structure was proved by XRD analysis, and of (Z)-3-benzoyl-5-{8-(2-methoxy-5-methylphenyl)-3,3,9-trimethyl-6-oxo-2-azaspiro[4.5]dec-7-en-1-ylidene}-4-phenylcyclopent-3-ene-1,2-dione.

  DOI：

  10.1134/s1070428013110110
• 作为产物：
  描述：

  甲基环氧丙烷 、 乙腈 、 1-甲氧基萘 在 硫酸 作用下， 以68%的产率得到2',5',5'-trimethyl-4',5'-dihydro-4H-spiro[naphthalene-1,3'-pyrrol]-4-one
  参考文献：
  名称：

  摘要：

  1-R-3,3-Dimethylbenzo[i]-2-azaspiro[4.5]deca-1,6-dien-8-ones or 1-R-3,3-dimethylbenzo[i]-2-azaspiro[4.5]deca-1,7-dien-6-ones were synthesized by three-component condensation of 1- or 2-methoxynaphthalene, isobutyraldehyde (or isobutylene oxide), and nitrile RCN in concentrated sulfuric acid.

  DOI：

  10.1023/a:1023479420744

文献信息

• Spirocyclohexadienones: XIII. Reactions of schiff bases with enamines derived from 3,4-dihydroisoquinoline and with spiro[naphthalene-1,3′-pyrrol]-4-one
  作者：V. A. Glushkov、G. F. Krainova、O. A. Maiorova、V. I. Karmanov、A. A. Gorbunov、P. A. Slepukhin

  DOI：10.1134/s1070428012040197

  日期：2012.4

  Addition of 1,3,3-trimethyl-3,4-dihydroisoquinolines to N-benzylideneanilines gives substituted N-[2-(3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-1-phenylethyl]anilines, whereas 2',5',5'-trimethyl-4',5'-dihydro-4H-spiro[naphthalene-1,3'-pyrrol]-4-one reacts with N-benzylideneanilines along two pathways involving cyclization to substituted 2,3,3a,4,10,11-hexahydrobenzo[f]pyrrolo[2,3-d]quinolin-5(1H)-ones or elimination of the aniline residue with formation of substituted 5',5'-trimethyl-2-styryl-4',5'-dihydro-4H-spiro[naphthalene-1,3'-pyrrol]-4-ones.
• Synthesis of dispiro hetero analogs of pyrrolizidine alkaloids
  作者：V. V. Konovalova、Yu. V. Shklyaev、A. N. Maslivets

  DOI：10.1134/s1070428012090205

  日期：2012.9
• Acylation of 2′,5′,5′-trimethyl-4′,5′-dihydro-4H-spiro-[naphthalene-1,3′-pyrrol]-4-one with 5-arylfuran-2,3-diones
  作者：V. V. Konovalova、Yu. V. Shklyaev、A. N. Maslivets

  DOI：10.1134/s1070428011070256

  日期：2011.7
• 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.
• 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
  作者：V. V. Konovalova、K. A. Galata、Yu. V. Shklyaev、A. N. Maslivets

  DOI：10.1134/s1070428013110171

  日期：2013.11

  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.