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。
• Diastereodivergent and Enantioselective Access to Spiroepoxides via Organocatalytic Epoxidation of Unsaturated Pyrazolones
  作者：Sara Meninno、Angelo Roselli、Amedeo Capobianco、Jacob Overgaard、Alessandra Lattanzi

  DOI：10.1021/acs.orglett.7b02189

  日期：2017.10.6

  amine–thioureas are effective catalysts for the first diastereo- and enantioselective epoxidation of unsaturated pyrazolones. The trans- or cis-spiroepoxides are preferentially obtained in good yield and high to excellent enantioselectivity using an appropriate organocatalyst and tert-butyl hydroperoxide as the oxidant. The epoxidation appears applicable to highly challenging β,β′-substituted unsaturated

  现成的手性胺-硫脲是不饱和吡唑啉酮的第一个非对映和对映选择性环氧化的有效催化剂。的反式-或顺式-spiroepoxides在良好收率和高使用适当的有机催化剂和优先获得优异的对映选择性叔丁基过氧化氢作为氧化剂。环氧化似乎适用于极富挑战性的β，β'-取代的不饱和吡唑啉酮，可接近带有两个邻位四元立体中心的螺环氧化物。该反应代表了Weitz-Scheffer环氧化的独特例子，其中催化剂控制的闭环步骤可用于制备两种对映体富集的非对映体环氧化物。
• 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.