1,1-dichloro-2,3,4,5-tetramethylsilole | 170308-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1,1-dichloro-2,3,4,5-tetramethylsilole
• 英文别名: 1,1-dichloro-2,3,4,5-tetramethyl-1-silacyclopenta-2,4-diene
• CAS: 170308-78-8
• 化学式: C₈H₁₂Cl₂Si
• 分子量: 207.175
• InChiKey: CHEFGIJZUFDNMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,1-dichloro-2,3,4,5-tetramethylsilole 在 lithium 作用下， 以 四氢呋喃 为溶剂， 生成 1,1-dilithio-2,3,4,5-tetramethylsilole
  参考文献：
  名称：

  Synthesis, solid-state structure, and reduction of 1,1-dichloro-2,3,4,5-tetramethylsilole

  摘要：

  The previously unknown 1,1-dichloro-2,3,4,5-tetramethyl-1-silacyclopenta-2,4-diene (3) was prepared in a three-step synthesis starting from zirconocene dichloride, 2-butyne, and n-butyllithium via bis(cyclopentadienyl)-2,3,4,5-tetramethyl-1-zirconacyclopenta-2,4-diene (1) and 1,4-diiodo-1,2,3,4-tetramethylbuta-1,3-diene (2).3 was characterized by NMR spectroscopy and single-crystal X-ray diffraction. Reaction of the new silole 3 with 4 equivalents of lithium in THF gives the corresponding dianion 4. H-1-, C-13-, and Si-29-NMR chemical shifts of 4 compared with 3 indicate some aromatic character for the ionic species. Trapping of 4 with Me(3)SiCl gives 1,1-bis(trimethylsilyl)-2,3,4,5-tetramethylsilole (5) in quantitative yield.

  DOI：

  10.1016/0022-328x(95)00333-l
• 作为产物：
  描述：

  2,5-dilithio-3,4-dimethylhexa-2,4-diene 在 四氯化硅 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 15.08h， 生成 1,1-dichloro-2,3,4,5-tetramethylsilole
  参考文献：
  名称：

  Synthesis, solid-state structure, and reduction of 1,1-dichloro-2,3,4,5-tetramethylsilole

  摘要：

  The previously unknown 1,1-dichloro-2,3,4,5-tetramethyl-1-silacyclopenta-2,4-diene (3) was prepared in a three-step synthesis starting from zirconocene dichloride, 2-butyne, and n-butyllithium via bis(cyclopentadienyl)-2,3,4,5-tetramethyl-1-zirconacyclopenta-2,4-diene (1) and 1,4-diiodo-1,2,3,4-tetramethylbuta-1,3-diene (2).3 was characterized by NMR spectroscopy and single-crystal X-ray diffraction. Reaction of the new silole 3 with 4 equivalents of lithium in THF gives the corresponding dianion 4. H-1-, C-13-, and Si-29-NMR chemical shifts of 4 compared with 3 indicate some aromatic character for the ionic species. Trapping of 4 with Me(3)SiCl gives 1,1-bis(trimethylsilyl)-2,3,4,5-tetramethylsilole (5) in quantitative yield.

  DOI：

  10.1016/0022-328x(95)00333-l

文献信息

• Direct Reactions of Zirconacyclopentadienes with Halosilanes as a Convenient Synthetic Method for Siloles
  作者：Ken-ichiro Kanno、Mitsuo Kira

  DOI：10.1246/cl.1999.1127

  日期：1999.10

  Direct reactions of 1,1-bis(cyclopentadienyl)zirconacyclopentadienes with various halosilanes afford the corresponding siloles in excellent yields. The reactions are very sensitive to the steric bulkiness of both zirconacyclopentadienes and halosilanes.

  1,1-双（环戊二烯基）锆并环戊二烯与各种卤代硅烷的直接反应以优异的产率提供相应的甲硅烷。该反应对锆基环戊二烯和卤代硅烷的空间体积非常敏感。
• Synthesis, solid-state structure, and reduction of 1,1-dichloro-2,3,4,5-tetramethylsilole
  作者：Uwe Bankwitz、Honglae Sohn、Douglas R. Powell、Robert West

  DOI：10.1016/0022-328x(95)00333-l

  日期：1995.9

  The previously unknown 1,1-dichloro-2,3,4,5-tetramethyl-1-silacyclopenta-2,4-diene (3) was prepared in a three-step synthesis starting from zirconocene dichloride, 2-butyne, and n-butyllithium via bis(cyclopentadienyl)-2,3,4,5-tetramethyl-1-zirconacyclopenta-2,4-diene (1) and 1,4-diiodo-1,2,3,4-tetramethylbuta-1,3-diene (2).3 was characterized by NMR spectroscopy and single-crystal X-ray diffraction. Reaction of the new silole 3 with 4 equivalents of lithium in THF gives the corresponding dianion 4. H-1-, C-13-, and Si-29-NMR chemical shifts of 4 compared with 3 indicate some aromatic character for the ionic species. Trapping of 4 with Me(3)SiCl gives 1,1-bis(trimethylsilyl)-2,3,4,5-tetramethylsilole (5) in quantitative yield.