[[(1R,8S)-10-[bis(trimethylsilyl)methyl]-1,8-dimethyl-9,11-dioxa-10-germatricyclo[6.2.1.02,7]undeca-2,4,6-trien-10-yl]-trimethylsilylmethyl]-trimethylsilane | 582299-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: [[(1R,8S)-10-[bis(trimethylsilyl)methyl]-1,8-dimethyl-9,11-dioxa-10-germatricyclo[6.2.1.02,7]undeca-2,4,6-trien-10-yl]-trimethylsilylmethyl]-trimethylsilane
• CAS: 582299-91-0
• 化学式: C₂₄H₄₈GeO₂Si₄
• 分子量: 553.576
• InChiKey: DEFJZMXZRSTECR-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.87
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-二乙酰苯 、 bis[bis(trimethylsilyl)methyl]germanium(II) 以 正己烷 为溶剂， 以82%的产率得到[[(1R,8S)-10-[bis(trimethylsilyl)methyl]-1,8-dimethyl-9,11-dioxa-10-germatricyclo[6.2.1.02,7]undeca-2,4,6-trien-10-yl]-trimethylsilylmethyl]-trimethylsilane
  参考文献：
  名称：

  Germylene Reactions with Quinones Shed Light on Germylene Phenone Equilibria

  摘要：

  Ge[CH(SiMe3)(2)](2) (1) and Ge[N(SiMe3)(2)](2) (2) react with anthraquinone and naphthoquinone in a 2:1 ratio to form five-membered rings with the carbonyl oxygens and the ortho carbons of the adjacent aromatic ring. The reaction with 1,4-diacetylbenzene proceeds in a similar fashion with 1; however no reaction is observed with 2. Compounds 1 and 2 react with 1,2-diacetylbenzene to yield a novel bicyclo species. In a previous report describing equilibria between 1 and phenones, it appeared that 2 did not undergo reaction to generate the five-membered ring with the accompanying formation of a conjugated triene. However, these quinone results indicate that an equilibrium can exist between 2 and a phenone moiety. In the reaction with quinones, a second equivalent of germylene effectively traps the conjugated triene by undergoing a 1,4-addition reaction. Unlike the initial triene formation, this second insertion is irreversible.

  DOI：

  10.1021/om0302589

文献信息

• Germylene Reactions with Quinones Shed Light on Germylene Phenone Equilibria
  作者：Ryan D. Sweeder、Robyn L. Gdula、Bonnie J. Ludwig、Mark M. Banaszak Holl、Jeff W. Kampf

  DOI：10.1021/om0302589

  日期：2003.8.1

  Ge[CH(SiMe3)(2)](2) (1) and Ge[N(SiMe3)(2)](2) (2) react with anthraquinone and naphthoquinone in a 2:1 ratio to form five-membered rings with the carbonyl oxygens and the ortho carbons of the adjacent aromatic ring. The reaction with 1,4-diacetylbenzene proceeds in a similar fashion with 1; however no reaction is observed with 2. Compounds 1 and 2 react with 1,2-diacetylbenzene to yield a novel bicyclo species. In a previous report describing equilibria between 1 and phenones, it appeared that 2 did not undergo reaction to generate the five-membered ring with the accompanying formation of a conjugated triene. However, these quinone results indicate that an equilibrium can exist between 2 and a phenone moiety. In the reaction with quinones, a second equivalent of germylene effectively traps the conjugated triene by undergoing a 1,4-addition reaction. Unlike the initial triene formation, this second insertion is irreversible.