5,5-dimethyl-2-phenylimino-Δ³-1,3,4-oxadiazoline | 77637-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,5-dimethyl-2-phenylimino-Δ³-1,3,4-oxadiazoline
• 英文别名: 2,2-dimethyl-5-(N-phenylimino)-1,3,4-oxadiazoline；(5,5-dimethyl-5H-[1,3,4]oxadiazol-2-ylidene)-phenyl-amine；5,5-Dimethyl-2-phenylimino-Δ³-1,3,4-oxadiazolin；5,5-dimethyl-N-phenyl-1,3,4-oxadiazol-2-imine
• CAS: 77637-40-2
• 化学式: C₁₀H₁₁N₃O
• 分子量: 189.217
• InChiKey: KZQGOKZLGUMWRY-UHFFFAOYSA-N

物化性质

• 沸点：
  241.5±23.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-2-phenylimino-Δ³-1,3,4-oxadiazoline 在 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 4-Methoxy-1,3,3-triphenylazetidin-2-one
  参考文献：
  名称：

  .beta.-Lactam-4-ylidenes

  摘要：

  beta-Lactam-4-ylidenes, generated by thermolysis of easily accessible spiro-fused beta-lactam oxadiazolines, are trapped in typical intramolecular and intermolecular carbene reactions.

  DOI：

  10.1021/jo00010a008
• 作为产物：
  描述：

  acetone 4-phenylsemicarbazone 在 碘苯二乙酸 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以93%的产率得到5,5-dimethyl-2-phenylimino-Δ³-1,3,4-oxadiazoline
  参考文献：
  名称：

  Hypervalent iodine oxidation of N-acylhydrazones and N-phenylsemicarbazone: an efficient method for the synthesis of derivatives of 1,3,4-oxadiazoles and .DELTA.3-1,3,4-oxadiazolines

  摘要：

  The oxidation of ketone N-acylhydrazones 1 by phenyliodine(III) diacetate (PIDA) in alcohol gave 2-alkoxy-DELTA3-1,3,4-oxadiazolines 4 in excellent yields, while the oxidative cyclization of aldehyde N-acylhydrazone 2 by PIDA in methanolic sodium acetate gave 2,5-disubstituted 1,3,4-oxadiazoles in good yields. The oxidation of acetone 4-phenylsemicarbazone afforded 2-(N-phenylimino)-DELTA3-1,3,4-oxadiazoline in excellent yield.

  DOI：

  10.1021/jo00064a027

文献信息

• Azetinone formation is not competitive with intermolecular reactions of a β-lactam-4-ylidene
  作者：Michel Zoghbi、John Warkentin

  DOI：10.1139/v92-355

  日期：1992.11.1

  3-Phenoxy-1-phenyl-2-azetidinon-4-ylidene (β-lactam-4-ylidene) 2a, was generated by thermolysis of a spiro-fused β-lactam oxadiazoline precursor (1). Fast 1,2-H migration, a characteristic reaction of singlet carbenes that would convert 2a to 3-phenoxy-1-phenyl-3-azetin-2-one (4a) could not be demonstrated. Added 1, 3-diphenylisobenzofuran (6) did not afford the [4 + 2] cycloadduct (7) expected from

  3-Phenoxy-1-phenyl-2-azetidinon-4-ylidene (β-lactam-4-ylidene) 2a 是通过热解螺-稠合 β-内酰胺恶二唑啉前体 (1) 产生的。无法证明快速 1,2-H 迁移，这是一种将 2a 转化为 3-phenoxy-1-phenyl-3-azetin-2-one (4a) 的单线态卡宾的特征反应。添加的 1, 3-二苯基异苯并呋喃 (6) 没有提供 4a 所预期的 [4 + 2] 环加合物 (7)，而是提供异构的 E- 和 Z-4-[1-(2-苯甲酰基苯基)-1-苯基]-methylene-3-phenoxy-1-phenylazetidin-2-ones (9)。这些化合物可以被合理化为 6 和亚基的第一次形成的 [2 + 1] 加合物的重排产物。9的Z异构体的结构是通过单晶X射线衍射确定的。在甲醇-d4 中生成 2a，无论是纯的还是
• Reaction of β-Lactam Carbenes with 2-Pyridyl Isonitriles: A One-Pot Synthesis of 2-Carbonyl-3-(pyridylamino)imidazo[1,2-<i>a</i>]pyridines Useful as Fluorescent Probes for Mercury Ion
  作者：Na Shao、Guang-Xian Pang、Cai-Xia Yan、Gao-Feng Shi、Ying Cheng

  DOI：10.1021/jo201273p

  日期：2011.9.16

  The one-pot reaction of beta-lactam carbenes with 2-pyridyl isonitriles followed by an acidic hydrolysis was reported, which produced 2-carbonyl-3-(pyridylamino)imidazo[1,2-a]pyridines in moderate to good yields. Among the resulting novel imidazo[1,2-a]pyridine derivatives, 1-(6-chloro-3-(5-chloropyridin-2-ylamino)imidazo [1,2-a]pyridin-2-yl)-2-ethylbutan-1-one was demonstrated to be an efficient fluorescent probe for mercury ion both in acetonitrile and in buffered aqueous solution.
• High Nucleophilicity of Cyclic Amidocarbene toward Aryl Isocyanates, New Approach to Spiro[azetidinone-4,3‘-indolinone] Derivatives
  作者：Ying Cheng、Bo Wang、Lan-Qing Cheng

  DOI：10.1021/jo060265h

  日期：2006.6.1

  The nucleophilic addition of beta-lactam-4-ylidenes 2, a type of ambiphilic cyclic amidocarbene, to aryl isocyanates has been studied and their application in organic synthesis has been demonstrated. Thermolysis of spiro[beta-lactam-4,2'-oxadiazolines] 1 in the presence of aryl isocyanates afforded both N-lactam and O-lactam substituted spiro[azetidine-2-one-4,3'-indole-2'-one] derivatives 5 and 6 in the total yield of 65-86%. Upon hydrolysis, products 5 and 6 were converted into spiro[azetidine-2-one-4,3'-indole-2'-one] 9 that was analogous to known biologically active compounds.
• Hypervalent iodine oxidation of N-acylhydrazones and N-phenylsemicarbazone: an efficient method for the synthesis of derivatives of 1,3,4-oxadiazoles and .DELTA.3-1,3,4-oxadiazolines
  作者：Ruiyang Yang、Lixin Dai

  DOI：10.1021/jo00064a027

  日期：1993.6

  The oxidation of ketone N-acylhydrazones 1 by phenyliodine(III) diacetate (PIDA) in alcohol gave 2-alkoxy-DELTA3-1,3,4-oxadiazolines 4 in excellent yields, while the oxidative cyclization of aldehyde N-acylhydrazone 2 by PIDA in methanolic sodium acetate gave 2,5-disubstituted 1,3,4-oxadiazoles in good yields. The oxidation of acetone 4-phenylsemicarbazone afforded 2-(N-phenylimino)-DELTA3-1,3,4-oxadiazoline in excellent yield.
• .beta.-Lactam-4-ylidenes
  作者：Michel Zoghbi、John Warkentin

  DOI：10.1021/jo00010a008

  日期：1991.5

  beta-Lactam-4-ylidenes, generated by thermolysis of easily accessible spiro-fused beta-lactam oxadiazolines, are trapped in typical intramolecular and intermolecular carbene reactions.