trimethyl-(7-trimethylsilyl-1-tricyclo[5.2.1.04,10]deca-2,4(10),5,8-tetraenyl)silane | 103148-69-2

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: trimethyl-(7-trimethylsilyl-1-tricyclo[5.2.1.04,10]deca-2,4(10),5,8-tetraenyl)silane
• CAS: 103148-69-2
• 化学式: C₁₆H₂₄Si₂
• 分子量: 272.538
• InChiKey: XSPPGFWHAYLBCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  trimethyl-(7-trimethylsilyl-1-tricyclo[5.2.1.04,10]deca-2,4(10),5,8-tetraenyl)silane 在 盐酸 、 水 作用下， 反应 10.0h， 以22%的产率得到4a,6a-Bis-trimethylsilanyl-6a,6b-dihydro-4aH-cyclopenta[cd]pentalen-2a-ol
  参考文献：
  名称：

  Syntheses, Structures, and Reactions of Highly Strained Dihydro- and Tetrahydroacepentalene Derivatives

  摘要：

  A versatile approach towards the highly strained acepentalene 3 via the readily accessible dipotassium acepentalenediide (10a) and the highly strained tetraenes 7 is reported, An unexpected [4+2] cycloaddition dimer 14 is formed upon protonation of the dipotassium acepentalenediide (10a) in 93% yield, and the monomeric 4,7-dihydroacepentalene (7a), as the reactive intermediate, can be trapped with anthracene to form the corresponding Diels-Alder adduct 16 in 15% yield. In contrast, the highly strained, but sterically protected monomeric bridgehead-bridgehead alkenes 7c,d can be isolated upon reaction of 10a or 10b with bulkli electrophiles, such as Me-3-SiCl and Me3SnCl, respectively. The X-ray crystal structure analysis of 7d exhibits a highly pyramidalized central double bond. The bisstannane 7d is an ideal precursor for acepentalene (3) which would be formed by removal of the two trimethylstannyl substituents. It can also be transmetallated to give the pure crystalline dilithium acepentalenediide (10b) in 78% yield. According to its H-1, Li-7 and C-13 NMR spectra, the bowl-shaped 12 pi-dianion in 10b is an aromatic species, and it undergoes a rapid bowl-to-bowl inversion at room temperature.

  DOI：

  10.1002/(sici)1521-3765(19980710)4:7<1192::aid-chem1192>3.0.co;2-g
• 作为产物：
  描述：

  triquinacene 在 正丁基锂 、 四甲基乙二胺 、 potassium tert-butylate 作用下， 以 正己烷 为溶剂， 反应 28.0h， 生成 trimethyl-(7-trimethylsilyl-1-tricyclo[5.2.1.04,10]deca-2,4(10),5,8-tetraenyl)silane
  参考文献：
  名称：

  Syntheses, Structures, and Reactions of Highly Strained Dihydro- and Tetrahydroacepentalene Derivatives

  摘要：

  A versatile approach towards the highly strained acepentalene 3 via the readily accessible dipotassium acepentalenediide (10a) and the highly strained tetraenes 7 is reported, An unexpected [4+2] cycloaddition dimer 14 is formed upon protonation of the dipotassium acepentalenediide (10a) in 93% yield, and the monomeric 4,7-dihydroacepentalene (7a), as the reactive intermediate, can be trapped with anthracene to form the corresponding Diels-Alder adduct 16 in 15% yield. In contrast, the highly strained, but sterically protected monomeric bridgehead-bridgehead alkenes 7c,d can be isolated upon reaction of 10a or 10b with bulkli electrophiles, such as Me-3-SiCl and Me3SnCl, respectively. The X-ray crystal structure analysis of 7d exhibits a highly pyramidalized central double bond. The bisstannane 7d is an ideal precursor for acepentalene (3) which would be formed by removal of the two trimethylstannyl substituents. It can also be transmetallated to give the pure crystalline dilithium acepentalenediide (10b) in 78% yield. According to its H-1, Li-7 and C-13 NMR spectra, the bowl-shaped 12 pi-dianion in 10b is an aromatic species, and it undergoes a rapid bowl-to-bowl inversion at room temperature.

  DOI：

  10.1002/(sici)1521-3765(19980710)4:7<1192::aid-chem1192>3.0.co;2-g

文献信息

• Syntheses, Structures, and Reactions of Highly Strained Dihydro- and Tetrahydroacepentalene Derivatives
  作者：Rainer Haag、Franz-Manfred Schüngel、Björk Ohlhorst、Thomas Lendvai、Holger Butenschön、Timothy Clark、Mathias Noltemeyer、Thomas Haumann、Roland Boese、Armin de Meijere

  DOI：10.1002/(sici)1521-3765(19980710)4:7<1192::aid-chem1192>3.0.co;2-g

  日期：1998.7.10

  A versatile approach towards the highly strained acepentalene 3 via the readily accessible dipotassium acepentalenediide (10a) and the highly strained tetraenes 7 is reported, An unexpected [4+2] cycloaddition dimer 14 is formed upon protonation of the dipotassium acepentalenediide (10a) in 93% yield, and the monomeric 4,7-dihydroacepentalene (7a), as the reactive intermediate, can be trapped with anthracene to form the corresponding Diels-Alder adduct 16 in 15% yield. In contrast, the highly strained, but sterically protected monomeric bridgehead-bridgehead alkenes 7c,d can be isolated upon reaction of 10a or 10b with bulkli electrophiles, such as Me-3-SiCl and Me3SnCl, respectively. The X-ray crystal structure analysis of 7d exhibits a highly pyramidalized central double bond. The bisstannane 7d is an ideal precursor for acepentalene (3) which would be formed by removal of the two trimethylstannyl substituents. It can also be transmetallated to give the pure crystalline dilithium acepentalenediide (10b) in 78% yield. According to its H-1, Li-7 and C-13 NMR spectra, the bowl-shaped 12 pi-dianion in 10b is an aromatic species, and it undergoes a rapid bowl-to-bowl inversion at room temperature.