2,2,7-trimethyl-5-phenyl-1-oxa-5,6-diazaspiro<2.4>hept-6-en-4-one | 36755-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2,2,7-trimethyl-5-phenyl-1-oxa-5,6-diazaspiro<2.4>hept-6-en-4-one
• 英文别名: 2,2,7-trimethyl-5-phenyl-1-oxa-5,6-diazaspiro[2.4]hept-6-en-4-one
• CAS: 36755-40-5
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: LBTZGZXYVZOIEM-UHFFFAOYSA-N

物化性质

• 熔点：
  74.5-76 °C(Solv: methanol (67-56-1))
• 沸点：
  391.3±35.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2,7-trimethyl-5-phenyl-1-oxa-5,6-diazaspiro<2.4>hept-6-en-4-one 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 0.08h， 以85%的产率得到4,5-dihydroxy-3-methyl-1-phenylpyrazole
  参考文献：
  名称：

  Kirschke, Klaus; Schmitz, Ernst, Journal fur praktische Chemie (Leipzig 1954), 1985, vol. 327, # 1, p. 35 - 44

  摘要：

  DOI：
• 作为产物：
  描述：

  4-isopropylidene-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one 在 间氯过氧苯甲酸 作用下， 生成 2,2,7-trimethyl-5-phenyl-1-oxa-5,6-diazaspiro<2.4>hept-6-en-4-one
  参考文献：
  名称：

  吡唑烷酮的光化学氧化

  摘要：

  吡唑烷酮（I）在丙酮照射下生成新型螺环氧化物（II）；异构体吡唑烷酮（IV）氧化二聚为（V）。

  DOI：

  10.1039/c39720000682

文献信息

• Synthesis and reactions of 4-isopropylidene-1-aryl-3-methyl-2-pyrazolin-5-ones
  作者：Jack Deruiter、Deborah Ann Carter、Wilmer Scott Arledge、Patrick J. Sullivan

  DOI：10.1002/jhet.5570240128

  日期：1987.1

  or piperidine, 4a-d failed to yield conjugate addition products, presumably due to the steric bulk provided by the two methyl substituents of the isopropylidene side chain. Reaction of 4a-d with hydrazine derivatives gave the 1-aryl-3-methyl-2-pyrazolin-5-ones 3a-d and isopropyl-hydrazones. Treatment of 4a with potassium cyanide yielded a stable conjugate addition product which exists as a mixture of

  在各种条件下研究了4-异亚丙基-1-芳基-3-甲基-2-吡唑啉-5-酮4a-d的反应。在硫醇或哌啶的存在下，4a-d未能产生共轭加成产物，这可能是由于异亚丙基侧链的两个甲基取代基所提供的空间体积。4a-d与肼衍生物反应，得到1-芳基-3-甲基-2-吡唑啉-5-酮3a-d和异丙基hydr。用氰化钾处理4a得到稳定的共轭加成产物，其以互变异构体的混合物形式存在于不同溶剂中。此外，用过氧化氢氧化4a可获得螺环氧化物22，而间氯过苯甲酸氧化既提供了螺环氧化物22，又提供了少量的羟基螺环氧化物23。
• Photochemical oxidation of pyrazolidinones
  作者：Seyhan N. Eǧe、Chih J. Tien、Andrea Dlesk、Bruce E. Potter、Bruce K. Eagleson

  DOI：10.1039/c39720000682

  日期：——

  Pyrazolidinone (I) gives the novel spiro-epoxide (II) on irradiation in acetone; the isomeric pyrazolidinone (IV) undergoes oxidative dimerization to (V).

  吡唑烷酮（I）在丙酮照射下生成新型螺环氧化物（II）；异构体吡唑烷酮（IV）氧化二聚为（V）。
• A Diversity-Oriented Approach to 1H-Pyrazole-4,5-diols, 4-Hydroxy-3H-pyrazol-3-ones, and Phenylhydrazones from Key Intermediate 4-Acetyloxy-3H-pyrazol-3-one
  作者：Hiroshi Maruoka、Eiichi Masumoto、Fumi Okabe、Toshihiro Fujioka、Kenji Yamagata

  DOI：10.3987/com-14-13094

  日期：——

  An approach to 1H-pyrazole-4,5-diols 4a-d, 4-hydroxy-3H-pyrazol-3-ones 5a-d, and phenylhydrazones 6a-d from key intermediate 4-acetyloxy-3H-pyrazol-3-one 3a is described. 4-Alkylidene-3H-pyrazol-3-ones 1a-c were reacted with m-chloroperbenzoic acid in the presence of potassium carbonate to give the corresponding spiroepoxide-3H-pyrazol-3-ones 2a-c. Treatment of 2a with acid anhydride such as acetic, propionic, butyric, and pentanoic anhydride in the presence of boron trifluoride diethyl etherate led to the corresponding 4-acyloxy-3H-pyrazol-3-ones 3a-d. The reactions of 3a with alpha-chloroketones, ketones, and/or secondary amines gave the corresponding 4a-d, 5a-d, and 6a-d.
• Ege, Seyhan N.; Adams, Alan. D.; Gess, E. Joseph, Journal of the Chemical Society. Perkin transactions I, 1983, p. 325 - 332
  作者：Ege, Seyhan N.、Adams, Alan. D.、Gess, E. Joseph、Ragone, Katherine S.、Kober, Brian J.、et al.

  DOI：——

  日期：——
• Synthesis and DNA Cleavage Activity of Functionalized Pyrazol-3-ones Containing Oxime Ester
  作者：Hiroshi Maruoka、Eiichi Masumoto、Nobuhiro Kashige、Fumi Okabe、Fumio Miake、Kenji Yamagata

  DOI：10.3987/com-16-13476

  日期：——

  A facile access to the synthesis of functionalized pyrazol-3-ones containing oxime ester from 4-hydroxypyrazol-3-ones, which were prepared starting from 4-alkylidenepyrazol-3-one, in moderate to good yields is reported. The structures of all products were identified by spectral data and some synthesized compounds were tested for their DNA cleavage activity.