2-azidocyclohex-2-enone | 161892-92-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidocyclohex-2-enone
• 英文别名: 2-Azidocyclohex-2-en-1-one
• CAS: 161892-92-8
• 化学式: C₆H₇N₃O
• 分子量: 137.141
• InChiKey: JGAPLVDZTGUZTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯酞 、 2-azidocyclohex-2-enone 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以65%的产率得到11-hydroxy-2,3,5,11-tetrahydro-1H-dibenzo[b,e]azepine-4,6-dione
  参考文献：
  名称：

  Anionic [4+3] heteroannulation of 2-azidoacrylates: a modular synthesis of 2-benzazepin-1-ones

  摘要：

  2-叠氮丙烯酸酯在低温的阴离子条件下与邻苯二甲酸酯发生[4+3]环化反应，生成5-羟基-2-苯并氮杂四环酮，其形成代表了叠氮氮杂环的构建新概念以及2-叠氮丙烯酸酯的新反应性。

  DOI：

  10.1039/c2cc30279a
• 作为产物：
  描述：

  7-氧杂二环[4.1.0]庚烷-2-酮 在 4-二甲氨基吡啶 、 叠氮磷酸二苯酯 、 lithium perchlorate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以68%的产率得到2-azidocyclohex-2-enone
  参考文献：
  名称：

  Ring opening reaction of epoxides with diphenyl phosphorazidate

  摘要：

  Diphenyl phosphorazidate with 4-dimethylaminopyridine and lithium perchlorate opens epoxides regio- and stereoselectively to give O-diphenylphosphoryl vicinal azidohydrins. For the alpha,beta-epoxy ketones and esters, only the corresponding alpha-azidovinyl ketones and esters were directly obtained, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01440-9

文献信息

• An Improved Procedure for the Conversion of Alkenes and Glycals to 1,2-Diazides Using Mn(OAc)₃·2H₂O in Acetonitrile Containing Trifluoroacetic Acid
  作者：Barry B. Snider*、Hong Lin

  DOI：10.1080/00397919808007024

  日期：1998.5

  Abstract Alkenes and Glycals react with Mn(OAc3)·2H2O and NaN3 in 9:1 acetonitrile-trifluoroacetic acid to give 1,2-diazides in >80% yield. Allylic azides are formed by slow addition of NaN3 to a mixture of alkene, Mn(OAc)3·2H2O and Cu(OAc)2.

  摘要 烯烃和乙二醇在 9:1 乙腈-三氟乙酸中与 Mn(OAc3)·2H2O 和 NaN3 反应生成 1,2-二叠氮化物，产率大于 80%。烯丙基叠氮化物是通过将 NaN3 缓慢加入烯烃、Mn(OAc)3·2H2O 和 Cu(OAc)2 的混合物中形成的。
• Vinyliminophosphorane-mediated preparation of 2-arylquinoline and 4-aryl-1-azaanthraquinone derivatives. X-Ray crystal structure of 1,2-dihydro-3H-indazolo[2,3-a]quinolin-4-one
  作者：Pedro Molina、Aurelia Pastor、María Jesús Vilaplana、Concepción Foces-Foces

  DOI：10.1016/0040-4020(94)01005-k

  日期：1995.1

  The reaction of the iminophosphorane derived from 3-azidocyclohexen-2-enone with substituted cinnamyl aldehydes affords 2-aryl-tetrahydroquinoline derivatives, which are easily converted into 2-arylquinolines. By contrast, iminophosphorane derived from 2-azidocyclohex-2-enone reacts only with α,β-unsaturated aldehydes without substituent at β-position to give 5,6-dihydro-8(7H)quinolinones. The iminophosphorane

  衍生自3-叠氮基环己烯-2-烯酮的亚氨基膦烷与取代的肉桂醛的反应提供了2-芳基-四氢喹啉衍生物，其易于转化为2-芳基喹啉。相比之下，衍生自2-叠氮基环己-2-烯酮的亚氨基磷烷仅与α，β-不饱和醛反应，在β-位没有取代基，得到5,6-二氢-8（7H）喹啉酮。衍生自2-叠氮基-1,4-萘醌的亚氨基磷烷与取代的肉桂醛反应，直接提供4-芳基-1-氮杂蒽醌。通过X射线分析已解决了1，2-二氢-3 H-吲唑并[2，3 - a ]喹啉-4-酮的晶体和分子结构。
• IMIDIAZOLE DERIVATIVES AND THEIR USE AS AGONISTS SELECTIVE AT ALPHA 2B OR 2B/2C ADRENERGIC RECEPTORS
  申请人：ALLERGAN, INC.

  公开号：EP1370533B1

  公开（公告）日：2015-05-06
• Anionic [4+3] heteroannulation of 2-azidoacrylates: a modular synthesis of 2-benzazepin-1-ones
  作者：Bidyut Kumar Dinda、Amit Kumar Jana、Dipakranjan Mal

  DOI：10.1039/c2cc30279a

  日期：——

  2-Azidoacrylates undergo [4+3] annulation with phthalides under anionic conditions at low temperatures to furnish 5-hydroxy-2-benzazepinones, the formation of which represents a new concept for the construction of azepines as well as a new reactivity of 2-azidoacrylates.

  2-叠氮丙烯酸酯在低温的阴离子条件下与邻苯二甲酸酯发生[4+3]环化反应，生成5-羟基-2-苯并氮杂四环酮，其形成代表了叠氮氮杂环的构建新概念以及2-叠氮丙烯酸酯的新反应性。
• Ring opening reaction of epoxides with diphenyl phosphorazidate
  作者：Masanori Mizuno、Takayuki Shioiri

  DOI：10.1016/s0040-4039(99)01440-9

  日期：1999.9

  Diphenyl phosphorazidate with 4-dimethylaminopyridine and lithium perchlorate opens epoxides regio- and stereoselectively to give O-diphenylphosphoryl vicinal azidohydrins. For the alpha,beta-epoxy ketones and esters, only the corresponding alpha-azidovinyl ketones and esters were directly obtained, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.