(E)-1-diazo-7-phenyl-6-hepten-2-one | 575451-15-9

• 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: (E)-1-diazo-7-phenyl-6-hepten-2-one
• 英文别名: (E)-1-diazo-7-phenylhept-6-en-2-one
• CAS: 575451-15-9
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: XDZRDFJFAWGUPY-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  19.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-diazo-7-phenyl-6-hepten-2-one 在 (NO⁺)Ru(II)-salen 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 7-phenylbicyclo[4.1.0]heptan-2-one 、 7-phenylbicyclo[4.1.0]heptan-2-one
  参考文献：
  名称：

  Asymmetric intramolecular cyclopropanation of diazo compounds with metallosalen complexes as catalyst: structural tuning of salen ligand

  摘要：

  Intramolecular cyclopropanation of alkenyl alpha-diazoacetates and alkenyl diazomethyl ketones was examined by using optically active (ON+)Ru(11)(salen) and Co(II)(salen) complexes as catalysts. For the cyclization of 2-alkenyl alpha-diazoacetates, Co(II)(salen) complexes 9 and 10 were found to be superior catalysts to the corresponding (ON+)Ru(11)(salen) complexes 4 and 5. On the other hand, (ON+)Ru(II)(salen) complex 2 was found to be the catalyst of choice for the cyclization of 3-alkenyl diazomethyl ketones, and complex 4 was found to be a good catalyst for the cyclization of (E)-4-alkenyl diazomethyl ketones. The present study demonstrates that metallosalen complexes, especially optically active (ON+)Ru(II)(salen) and Co(11)(salen) complexes, can serve as efficient catalysts for the cyclization of alkenyl diazocarbonyl compounds, if a suitable salen ligand is used as the chiral auxiliary. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00167-8
• 作为产物：
  描述：

  4-羧丁基三苯基溴化膦 在 草酰氯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.5h， 生成 (E)-1-diazo-7-phenyl-6-hepten-2-one
  参考文献：
  名称：

  硝基与4-戊烯基和环丙基烯酮的反应：通往5-己烯基和环丙基甲基的新途径。

  摘要：

  4-戊烯基酮4a和9以及环丙基烯酮3a，13、14（RCH = C = O）是通过光化学Wolff重排生成的，并且在室温下在烃类溶剂中被IR观察为相对长寿的物种。这些烯酮与硝基氧基四甲基哌啶基氧基（TEMPO，TO *）和四甲基异吲哚啉-2-氧基（TMIO，IO *）的反应形成羧基取代的5-己烯基和环丙基甲基，它们被第二个硝基氧基所俘获或进行重排通过诱捕。4a与TEMPO的反应速率常数与n-BuCH = C = O（1b）相似，而3a的反应速率高4.3倍，表明初始自由基的环丙基稳定性。

  DOI：

  10.1021/jo0102922

文献信息

• Safe and Reliable Synthesis of Diazoketones and Quinoxalines in a Continuous Flow Reactor
  作者：Laetitia J. Martin、Andreas L. Marzinzik、Steven V. Ley、Ian R. Baxendale

  DOI：10.1021/ol1027927

  日期：2011.1.21

  A flow method for the synthesis of aliphatic and aromatic diazoketones from acyl chloride precursors has been developed and used to prepare quinoxalines in a multistep sequence without isolation of the potentially explosive diazoketone. The protocol showcases an efficient in-line purification using supported scavengers with time-saving and safety benefits and in particular a reduction in the operator's exposure to carcinogenic phenylenediamines.