(Z)-1-diazo-6-phenyl-5-hexen-2-one | 479680-38-1

• 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: (Z)-1-diazo-6-phenyl-5-hexen-2-one
• 英文别名: (Z)-1-diazo-6-phenylhex-5-en-2-one
• CAS: 479680-38-1
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: PPJDBVAMZLZOIE-YWEYNIOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  (Z)-1-diazo-6-phenyl-5-hexen-2-one 在 (NO⁺)Ru(II)-salen 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 6-phenylbicyclo[3.1.0]hexan-2-one 、 6-phenylbicyclo[3.1.0]hexan-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：

  在 sodium hydroxide 作用下， 反应 0.5h， 生成 (Z)-1-diazo-6-phenyl-5-hexen-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

文献信息

• Highly Enantioselective Intramolecular Cyclopropanation of Alkenyl Diazo Ketones Using Ru(salen) as Catalyst
  作者：Biswajit Saha、Tatsuya Uchida、Tsutomu Katsuki

  DOI：10.1246/cl.2002.846

  日期：2002.8

  Intramolecular cyclopropanation of alkenyl diazoketones was found to proceed in a highly enantioselective manner by using optically active (nitroso)(salen)ruthenium(II) complex 1 as the catalyst under photo-irradiation.

  通过使用光学活性 (亚硝基)(salen) 钌 (II) 配合物 1 作为催化剂，在光照射下，发现烯基重氮酮的分子内环丙烷化以高度对映选择性的方式进行。