1-phenyl-5-(trimethylsilyl)-1,5-pentanedione | 143370-58-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenyl-5-(trimethylsilyl)-1,5-pentanedione
• 英文别名: 1-Phenyl-5-trimethylsilylpentane-1,5-dione
• CAS: 143370-58-5
• 化学式: C₁₄H₂₀O₂Si
• 分子量: 248.397
• InChiKey: XAGTVPRPJNKKBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  c-1-benzoyl-r-2-(phenylseleno)-2-(trimethylsilyl)cyclobutane 在 水 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以39%的产率得到1-phenyl-5-(trimethylsilyl)-1,5-pentanedione
  参考文献：
  名称：

  Selenium-directed stereoselective [2 + 2] cycloaddition reactions promoted by Lewis acids: a novel zwitterionic intermediate

  摘要：

  The reaction of (trimethylsilyl)vinyl selenide 1 and (trimethylsilyl)allenyl selenide 2 with vinyl ketones 3a-c in the presence of a Lewis acid gave cyclobutane derivatives stereoselectively. The reaction of 1 and 3a-c with SnCl4 was quenched either with Et3N to give cyclobutanes 4a-c or with H2O to give acylsilanes 11a-c. The formation of both products is explained in terms of a zwitterionic intermediate. The cis relationship between the phenylseleno group and the carbonyl group of 4a-c is rationalized by consideration of a combination of secondary-orbital interactions and steric effects in the early stage of intermediate formation.

  DOI：

  10.1021/jo00047a013

文献信息

• Generation of β-Keto Radicals from Cyclopropanols Catalyzed by AgNO₃
  作者：Shunsuke Chiba、Zhengyan Cao、Serry Atta Atta El Bialy、Koichi Narasaka

  DOI：10.1246/cl.2006.18

  日期：2006.1

  Various β-keto radicals are generated from cyclopropanols by treatment with a catalytic amount of AgNO3 and (NH4)2S2O8 as a reoxidant in the presence of pyridine. Thus, generated β-keto radicals react with alkenes to yield addition products.

  通过用催化量的硝酸银和重铬酸铵作为氧化剂在吡啶存在下处理环丙醇，可以生成各种β-酮自由基。生成的β-酮自由基与烯烃反应，生成加成产物。
• Selenium-directed stereoselective [2 + 2] cycloaddition reactions promoted by Lewis acids: a novel zwitterionic intermediate
  作者：Shoko Yamazaki、Hiroyuki Fujitsuka、Shinichi Yamabe、Hatsue Tamura

  DOI：10.1021/jo00047a013

  日期：1992.10

  The reaction of (trimethylsilyl)vinyl selenide 1 and (trimethylsilyl)allenyl selenide 2 with vinyl ketones 3a-c in the presence of a Lewis acid gave cyclobutane derivatives stereoselectively. The reaction of 1 and 3a-c with SnCl4 was quenched either with Et3N to give cyclobutanes 4a-c or with H2O to give acylsilanes 11a-c. The formation of both products is explained in terms of a zwitterionic intermediate. The cis relationship between the phenylseleno group and the carbonyl group of 4a-c is rationalized by consideration of a combination of secondary-orbital interactions and steric effects in the early stage of intermediate formation.