(3,3-二甲基-1-丁炔基)三甲基锡烷 | 34664-54-5

• 分子结构分类: 有机化合物
• 中文名称: (3,3-二甲基-1-丁炔基)三甲基锡烷
• 英文名称: (3,3-dimethyl-1-butynyl)trimethylstannane
• 英文别名: trimethyl(3,3-dimethyl-1-butynyl)tin；(3,3-dimethylbut-1-yn-1-yl)trimethylstannane；tert.-butyl(trimethylstannyl)acetylene；3,3-Dimethylbut-1-ynyl(trimethyl)stannane
• CAS: 34664-54-5
• 化学式: C₉H₁₈Sn
• 分子量: 244.952
• InChiKey: YQXIHQLFVHROFF-UHFFFAOYSA-N

物化性质

• 沸点：
  80-84 °C(Press: 20 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (3,3-二甲基-1-丁炔基)三甲基锡烷 在 manganese(IV) oxide 、 二(氰基苯)二氯化钯 、 samarium diiodide 、 三叔丁基膦 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 52.67h， 生成 C₆₄H₇₈Br₄N₄Si₂
  参考文献：
  名称：

  过烷基化的四氮杂并苯衍生物。

  摘要：

  描述了十乙炔基化的四氮杂并五苯的合成。它是通过缩合反应得到两个吡嗪环并随后进行连续的斯蒂勒型偶联而获得的。这是被过炔基化的任何高级（杂）并苯的第一个例子。四个氮原子的存在消除了取代炔基的周边相互作用，从而产生了这种岩石稳定且高度扭曲的杂并苯。

  DOI：

  10.1002/chem.201904087
• 作为产物：
  描述：

  3,3-二甲基-1-丁炔 、 2-(三甲基甲锡烷基)吡啶 在 [(pentamethylcyclopentadienyl)2La(hydrido)]2 作用下， 以 氘代苯 、 氘代甲苯 为溶剂， 反应 72.0h， 生成 (3,3-二甲基-1-丁炔基)三甲基锡烷
  参考文献：
  名称：

  Carbostannolysis Mediated by Bis(pentamethylcyclopentadienyl)lanthanide Catalysts. Utility in Accessing Organotin Synthons

  摘要：

  Facile carbon tin bond activation in the reaction of 2-(trimethylstannyl)pyridine (1) with the organolanthanide complexes Cp-2*LaCH(TMS)(2) (2a) and [Cp-2*LaH](2) (2b) yields Cp-2*La(2-pyridyl) (3), as well as Me3SnCH(TMS)(2) and Me3SnH, respectively. At room temperature, ethylene then undergoes insertion into the resulting La C(pyridyl) bond followed by carbostannolysis to catalytically generate 2-(2-(Me3Sn)ethyl)pyridine (4) or, with extended reaction times, 6-ethyl-2-(2(trimethylstannyl)ethyl)pyridine (5). In contrast to 1, 6-methyl-2(trimethylstannyl)pyridine (6) is unreactive, likely reflecting steric constraints. With terminal alkynes, this catalytic heterocycle-SnMe3 activation/carbostannylation process affords tin-functionalized conjugated enynes. Thus, at 60 degrees C 2b catalyzes the conversion 1 + 1-hexyne to yield (E)-2-butyl-1-(Me3Sn)-oct-1-en-3-yne in a 60:1 ratio E:Z isomer ratio. This reaction is available to alpha-monosubstituted and alpha-disubstituted terminal alkynes, while alpha-trisubstituted alkynes are too hindered for reaction. The catalytic cycle is proposed to proceed via a spectroscopically detectable Me3Sn-alkynyl intermediate which undergoes insertion into a Cp-2*La-alkynyl bond to produce the conjugated alkynyl product, which is subsequently protonolyzed from the 2-La center by a new terminal alkyne substrate molecule. NMR spectroscopic and kinetic data support the proposed pathway and indicate turnover-limiting alkyne insertion.

  DOI：

  10.1021/om301031e

文献信息

• Unexpected products from the reaction of alkynylstannanes with 9-borabicyclo[3.3.1]nonane
  作者：Bernd Wrackmeyer、Christoph Bihlmayer

  DOI：10.1039/c39810001093

  日期：——

  The reaction of 9-borabicyclo[3.3.1]nonane with alkynyltrimethylstannanes (Me3Sn–CC–R) yields a new alkene (R = But) and new allenes (R = Me3Si or Me3Sn); the formation of both types of compound is not consistent with hydroboration but involves exchange reactions, alkynyl borate intermediates, and organoboration.

  9-borabicyclo [3.3.1]壬烷与炔基三甲基锡烷（Me 3 Sn–C C–R）的反应生成新的烯烃（R = Bu t）和新的烯（R = Me 3 Si或Me 3 Sn）；两种化合物的形成都与硼氢化反应不符，但涉及交换反应，硼酸炔基中间体和有机硼化。
• Silicon-, germanium- and tin-substituted acetylenes and their dicobalt hexacarbonyl complexes
  作者：Dietmar Seyferth、David L. White

  DOI：10.1016/s0022-328x(00)82641-8

  日期：1971.11

  number of Group IV element-substituted acetylenes have been prepared, including the new Me3SiCCSiMe2H, Me2HSiCCSiMe2H, Me3SiCCCMe3 and Me3SnCCCMe3. The dicobalt hexacarbonyl complexes of Me3SnCCSnMe3, Me3SnCCH, Me3GeCCGeMe3, Me3SnCCCMe3, Me3GeCCSiMe3 and Me3SnCCSiMe3 have been prepared by reaction of the appropriate acetylene with dicobalt octacarbonyl. Reaction of (Me3SnC2H)Co2(CO)6 and (

  许多IV族元素取代的乙炔的已经制备，其中包括新的我3 SiCCSiMe 2 H，我2 HSiCCSiMe 2 H，我3 SiCCCMe 3和Me 3 SnCCCMe 3。ME的六羰基二钴复合物3 SnCCSnMe 3中，Me 3 SnCCH中，Me 3 GeCCGeMe 3中，Me 3 SnCCCMe 3中，Me 3 GeCCSiMe 3和Me 3 SnCCSiMe 3通过适当的乙炔与二羰基二羰基八羰基化合物的反应制备α-己内酰胺。（Me 3 SnC 2 H）Co 2（CO）6和（Me 3 SnC 2 CMe 3）-Co 2（CO）6与二氯甲烷中的CH 3 COCl / AlCl 3反应，得到（CH 3 COC 2 H）Co 2-（CO）6和（CH 3 COC 2 CMe 3）Co 2（CO）6。
• Synthesis, Structure, and Reaction of 1-Alkynyl(aryl)-λ³-bromanes
  作者：Masahito Ochiai、Yoshio Nishi、Satoru Goto、Motoo Shiro、Hermann J. Frohn

  DOI：10.1021/ja038777q

  日期：2003.12.1

  Reported here for the first time are the synthesis, structure, and reaction of hypervalent 1-alkynyl(aryl)-λ3-bromanes. BF3-catalyzed ligand exchange on bromine(III) of p-trifluoromethylphenyl(difluoro)-λ3-bromane with 1-alkynyl(trimethyl)stannanes in dichloromethane at −78 °C afforded 1-alkynyl(aryl)-λ3-bromanes in good yields. Trimethyl(trimethylsilylethynyl)stannane gave silylethynyl-λ3-bromane

  这里首次报道了高价 1-炔基（芳基）-λ3-溴烷的合成、结构和反应。在-78 °C 的二氯甲烷中，BF3 催化对三氟甲基苯基（二氟）-λ3-溴与 1-炔基（三甲基）锡烷的溴（III）进行配体交换，以良好的产率得到 1-炔基（芳基）-λ3-溴. 三甲基（三甲基甲硅烷基乙炔基）锡烷选择性地生成甲硅烷基乙炔基-λ3-溴烷。将炔基溴烷的炔碳原子的 13C NMR 化学位移与炔基-λ3-碘烷的化学位移进行比较，并根据自旋轨道诱导的重原子效应进行解释。叔丁基乙炔基溴的结构是通过其冠醚配合物的单晶 X 射线分析确定的。
• Phenylboration of Monoalkyn-1-yltin Compounds
  作者：Bernd Wrackmeyer、Oleg L. Tok、Wolfgang Milius

  DOI：10.1515/znb-2007-1207

  日期：2007.12.1

  The 1 : 1 reactions of triphenylborane 1 with monoalkyn-1-yltin compounds Me₃Sn-C≡C-R¹ 2 [R¹ = ^tBu (a), Ph (b), ferrocenyl (c), Si(H)Me₂ (d), SnMe₃ (e)] afford mainly (> 80 %) the corresponding alkene derivatives 3 by 1,1-phenylboration. Exchange B-Ph/Sn-C≡C-R¹ takes place as a side reaction. The corresponding 1 : 2 reaction with 2b leads to the dialkenylborane 4b (R¹ = Ph), of which the molecular structure could be determined by X-ray analysis. In contrast, the 1 : 2 reaction with 2e gave an allene derivative 5e. The solution-state structures of compounds 3 - 5 have been confirmed by ¹H, ¹¹B, ¹³C and ¹¹⁹Sn NMR spectroscopy.

  三苯基硼烷1与单炔基锡化合物Me3Sn-C≡C-R1 2 [R1 = tBu (a), Ph (b), ferrocenyl (c), Si(H)Me2 (d), SnMe3 (e)] 的1:1反应主要产生相应的烯烃衍生物3，产率大于80％，通过1,1-苯基硼化反应。B-Ph/Sn-C≡C-R1的交换作为副反应发生。与2b的相应1:2反应导致双烯基硼烷4b (R1 = Ph)，其分子结构可通过X射线分析确定。相反，与2e的1:2反应产生了联烯衍生物5e。化合物3 - 5的溶液态结构已通过1H、11B、13C和119Sn核磁共振波谱确认。
• Organoborierung von alkinylstannanen
  作者：Bernd Wrackmeyer

  DOI：10.1016/s0022-328x(00)82931-9

  日期：1981.1

  The formation in high yields of various substituted allenes by the reaction of triethylborane with alkynyl stannanes is reported. NMR data (1H, 11B, 13C, 119Sn) of the allenes and of their derivatives prepared by the reaction of the allenes with acetic acid prove the proposed structures.

  据报道，通过三乙基硼烷与炔基锡烷的反应以高产率形成各种取代的烯。通过烯丙基与乙酸反应制备的烯丙基及其衍生物的NMR数据（1 H，11 B，13 C，119 Sn）证明了所提出的结构。

表征谱图