1,1-dimethyl-2,5-dihydrostannole | 1147101-10-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: 1,1-dimethyl-2,5-dihydrostannole
• 英文别名: 1,1-dimethyl-1-stannylcyclopent-3-ene；1,1-dimethylstannacyclopent-3-ene；C4H6SnMe2
• CAS: 1147101-10-7；207121-01-5
• 化学式: C₆H₁₂Sn
• 分子量: 202.871
• InChiKey: WKTLHZYBVRTCPH-FGSKAQBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  7.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1,1-dimethyl-2,5-dihydrostannole 在 C₂H₅Br or 3-hexyne 作用下， 以 neat (no solvent) 为溶剂， 生成 二甲基锡
  参考文献：
  名称：

  Synthesis of 1-Stannacyclopent-3-enes and Their Pyrolysis to Stannylenes

  摘要：

  1,1-Diorgano-1-stannacyclopent-3-enes have been synthesized by condensation in THF of magnesium complexes of 1,3-dienes and dichlorodiorganostannanes. 1, 1-Dimethyl-, 1, 1-di-n-butyl-,1, 1-di-tert-butyl-, and 1,1-diphenyl-1-stannacyclopent-3-enes and 1,1,3,4-tetramethyl-, 1,1-di-tert-butyl-3,4-dimethyl-, and 3,4-dimethyl-1,1-diphenyl-1-stannacyclopent-3-enes were prepared. Kinetic studies of the pyrolysis. at temperatures as low as 75 degrees C of several of these stannacyclopent-3-enes resulted in their first-order disappearance, consistent with a unimolecular dissociation to the corresponding stannylene and diene. Activation parameters are reported. Trapping of dimethylstannylene by dienes was overwhelmed by oligomerization of Me2Sn::, but for t-Bu2Sn: a high yield of diene adduct was obtained. The dimethylstannylene oligomer(s) functioned as stannylenoids and were responsible for several reactions previously attributed to free Me2Sn:. cyclo-(t-Bu2Sn)(4) may also function as a stannylenoid.

  DOI：

  10.1021/om800541f
• 作为产物：
  描述：

  二甲基二氯化锡 、 (2-丁烯-1,4-二基)镁 以 四氢呋喃 为溶剂， 以15%的产率得到1,1-dimethyl-2,5-dihydrostannole
  参考文献：
  名称：

  Synthesis of 1-Stannacyclopent-3-enes and Their Pyrolysis to Stannylenes

  摘要：

  1,1-Diorgano-1-stannacyclopent-3-enes have been synthesized by condensation in THF of magnesium complexes of 1,3-dienes and dichlorodiorganostannanes. 1, 1-Dimethyl-, 1, 1-di-n-butyl-,1, 1-di-tert-butyl-, and 1,1-diphenyl-1-stannacyclopent-3-enes and 1,1,3,4-tetramethyl-, 1,1-di-tert-butyl-3,4-dimethyl-, and 3,4-dimethyl-1,1-diphenyl-1-stannacyclopent-3-enes were prepared. Kinetic studies of the pyrolysis. at temperatures as low as 75 degrees C of several of these stannacyclopent-3-enes resulted in their first-order disappearance, consistent with a unimolecular dissociation to the corresponding stannylene and diene. Activation parameters are reported. Trapping of dimethylstannylene by dienes was overwhelmed by oligomerization of Me2Sn::, but for t-Bu2Sn: a high yield of diene adduct was obtained. The dimethylstannylene oligomer(s) functioned as stannylenoids and were responsible for several reactions previously attributed to free Me2Sn:. cyclo-(t-Bu2Sn)(4) may also function as a stannylenoid.

  DOI：

  10.1021/om800541f

文献信息

• Direct Detection of Dimethylstannylene and Tetramethyldistannene in Solution and the Gas Phase by Laser Flash Photolysis of 1,1-Dimethylstannacyclopent-3-enes
  作者：Rosa Becerra、Peter P. Gaspar、Cameron R. Harrington、William J. Leigh、Ignacio Vargas-Baca、Robin Walsh、Dong Zhou

  DOI：10.1021/ja052675d

  日期：2005.12.1

  stannylene has been trapped as the Sn-H insertion product upon photolysis of 4a in hexane containing trimethylstannane. Flash photolysis of 4a in the gas phase affords a transient absorbing in the 450-520-nm range that is assigned to SnMe2 by comparison of its spectrum and reactivity to those previously reported from other precursors. Flash photolysis of 4b in hexane solution affords results consistent with

  1,1-二甲基-和 1,1,3,4-四甲基锡环戊-3-烯（分别为 4a 和 4b）的光化学在气相和己烷溶液中通过稳态和 193 nm 激光进行了研究闪光光解法。这两种化合物的光解导致形成 1,3-丁二烯（来自 4a）和 2,3-二甲基-1,3-丁二烯（来自 4b）作为主要产物，这表明产生二甲基亚锡 (SnMe2) 的环回复是这些分子的主要光分解途径。事实上，在含有三甲基锡烷的己烷中光解 4a 时，亚锡苯已作为 Sn-H 插入产物被捕获。4a 在气相中的闪光光解提供了 450-520 nm 范围内的瞬态吸收，通过将其光谱和反应性与先前报道的其他前体的光谱和反应性进行比较，将其分配给 SnMe2。4b 在己烷溶液中的闪光光解提供的结果与 SnMe2 的初始形成一致（λ(max) 约 500 nm），其衰减超过约 10 微米以形成四甲基二锡烯（5b；λ(max) 约 470 nm）。distannene
• Synthesis of 1-Stannacyclopent-3-enes and Their Pyrolysis to Stannylenes
  作者：Dong Zhou、Clemens Reiche、Mrinmoy Nag、John A. Soderquist、Peter P. Gaspar

  DOI：10.1021/om800541f

  日期：2009.4.27

  1,1-Diorgano-1-stannacyclopent-3-enes have been synthesized by condensation in THF of magnesium complexes of 1,3-dienes and dichlorodiorganostannanes. 1, 1-Dimethyl-, 1, 1-di-n-butyl-,1, 1-di-tert-butyl-, and 1,1-diphenyl-1-stannacyclopent-3-enes and 1,1,3,4-tetramethyl-, 1,1-di-tert-butyl-3,4-dimethyl-, and 3,4-dimethyl-1,1-diphenyl-1-stannacyclopent-3-enes were prepared. Kinetic studies of the pyrolysis. at temperatures as low as 75 degrees C of several of these stannacyclopent-3-enes resulted in their first-order disappearance, consistent with a unimolecular dissociation to the corresponding stannylene and diene. Activation parameters are reported. Trapping of dimethylstannylene by dienes was overwhelmed by oligomerization of Me2Sn::, but for t-Bu2Sn: a high yield of diene adduct was obtained. The dimethylstannylene oligomer(s) functioned as stannylenoids and were responsible for several reactions previously attributed to free Me2Sn:. cyclo-(t-Bu2Sn)(4) may also function as a stannylenoid.