三甲基(1-苯基乙烯基)锡烷 | 1198-01-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 三甲基(1-苯基乙烯基)锡烷
• 英文名称: Me3SnCPhCH2
• 英文别名: trimethyl(1-phenylethenyl)stannane；Stannane, trimethyl(1-phenylethenyl)-
• CAS: 1198-01-2
• 化学式: C₁₁H₁₆Sn
• 分子量: 266.958
• InChiKey: QNWNEKZJEDMYSS-UHFFFAOYSA-N

物化性质

• 沸点：
  110 °C(Press: 2 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  三甲基(1-苯基乙烯基)锡烷 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 三甲基氯化锡
  参考文献：
  名称：

  苯基取代的乙烯基锡烷：亲电取代反应中的合成和反应性。

  摘要：

  Seven phenyl-substituted vinylstannanes have been prepared. (Z)-beta-(trimethylstannyl)styrene, alpha-(trimethylstannyl)styrene, and 1,1-diphenyl-2-(trimethylstannyl)ethene were prepared by Grignard coupling between the appropriate phenyl-substituted vinyl bromide and chlorotrimethylstannane. (E)-beta-(Trimethylstannyl)styrene and (Z)-(trimethylstannyl)stilbene were prepared by AIBN catalyzed hydrostannation of the appropriate phenyl-substituted acetylene. (E)-(Trimethylstannyl)stilbene and methyl (E)-2-(trimethylstannyl)cinnamate were prepared by palladium(0) catalyzed hydrostannation of diphenylacetylene and methyl phenylpropiolate, respectively. Each compound was characterized by H-1, C-13, and Sn-119 NMR. Reactivity of each compound to protodestannylation was determined by spectrophotometric or H-1 NMR measurement of second order rate constants. The relative reactivity is interpreted on the basis of the electronic and steric effects of the phenyl substituents. The stereochemistry of destannylation resulted in retention of configuration for four of the compounds, consistent with an S(E)2 mechanism. However, methyl (E)-2-(trimethylstannyl)cinnamate gave an E/Z product ratio of essentially. This result is consistent with an allenol mechanism for protodestannylation of this compound.

  DOI：

  10.1021/om00015a031
• 作为产物：
  描述：

  三甲基溴化锡 、 magnesium,ethenylbenzene,bromide 以 四氢呋喃 为溶剂， 生成 三甲基(1-苯基乙烯基)锡烷
  参考文献：
  名称：

  Bai, L. I.; Yakubovich, A. Ya.; Muler, L. I., Zhurnal Obshchei Khimii, 1964, vol. 34, p. 3746 - 3746

  摘要：

  DOI：

文献信息

• Functionally substituted organotins: formation of organotin-containing phosphines
  作者：Terence N. Mitchell、Heinz-Joachim Belt

  DOI：10.1016/0022-328x(88)80105-0

  日期：1988.5

  Additions of PH bonds to vinylstannes, of SnH bonds to alkynylphosphines, and of SnP bonds to allenes and alkynes are described.

  描述了将PstanH键加到乙烯基锡上，将SnH键加到炔基膦上，以及将SnP键加到丙二烯和炔上的方法。
• Regio- and stereo-selective synthesis of vinylstannanes. Transition-metal catalyzed stannylmetalation of acetylenes and conversion of enol triflates and vinyl iodides into vinylstannanes
  作者：Seijiro Matsubara、Jun-Ichi Hibino、Yoshitomi Morizawa、Koichiro Oshima、Hitosi Nozaki

  DOI：10.1016/0022-328x(85)87365-4

  日期：1985.4

  Two new methods for the regio- and stereo-selective synthesis of vinylstannanes are described. (i) The reaction of terminal acetylenes with n-Bu3SnMgMe, n-Bu3SnAlEt2, or (n-Bu3Sn)2Zn in the presence of various transition-metal catalysts provides vinylstannanes in good yields. Whereas copper-catalyzed stannylmagnesation of 4-benzyloxy-1-butyne gives (E)-4-benzyloxy-1-tributylstannyl-1-butene exclusively

  描述了乙烯基锡烷的区域和立体选择性合成的两种新方法。（i）在各种过渡金属催化剂存在下，末端乙炔与n-Bu 3 SnMgMe，n-Bu 3 SnAlEt 2或（n-Bu 3 Sn）2 Zn的反应提供了高产率的乙烯基锡烷。铜催化的4-苄氧基-1-丁炔的苯乙烯甲基化仅得到（E）-4-苄氧基-1-三丁基锡烷基-1-丁烯，而钯催化的苯乙烯化锌则优先提供4-苄氧基-2-三丁基锡烷基-1-丁烯。（ii）在CuCN催化剂存在下用Me 3 Sn-MgMe处理烯醇三氟甲磺酸酯或碘乙烯，得到高产率的乙烯基锡烷。
• Reaction of diazonium salts with transition metals
  作者：Kiyoshi Kikukawa、Hideto Umekawa、Tsutomu Matsuda

  DOI：10.1016/0022-328x(86)80264-9

  日期：1986.9

  Under palladium(0) catalysis, Ph(R3Sn)CCH2 (R = Me, Et and Bu) easily reacted with ArN2BF4 (Ar = XPh, X = H, 4-Me, 4-I, 4-MeCO, 4-EtOCO, 3-NO2 and 4-NO2) and selectively produced (Z)-PhCHCHAr but not Ph(Ar)CCH2. An addition-elimination mechanism instead of the transmetallation from tin to palladium is postulated for this unusual regiochemistry.

  在钯（0）催化中，Ph（R 3 Sn）的CCH 2（R =甲基，乙基和丁基）容易地与反应ARN 2 BF 4（AR = XPH，X = H，4-Me中，4-I， 4-MeCO，4-EtOCO，3-NO 2和4-NO 2）并选择性地生成（Z）-PhCH = CHAr，而不是Ph（Ar）C = CH 2。对于这种不寻常的区域化学，假定了一种加成消除机制，而不是从锡向钯的金属转移。
• Generation and reactions of 1-(2-indolyl)vinylcopper derivatives with pyridinium salts
  作者：M.-Lluı̈sa Bennasar、Cecı́lia Juan、Tomàs Roca、Manuel Monerris、Joan Bosch

  DOI：10.1016/s0040-4020(01)01065-1

  日期：2001.12

  1-(2-Indolyl)vinylstannane 1b has been transmetallated into both the corresponding HO mixed cyanocuprate and the Cu-catalysed organomagnesium reagent, and the reactivity of these species towards N-alkyl-3-acylpyridinium salts 8 and 17 has been tested.

  1-（2-吲哚基）乙烯基锡烷1b已被金属转移到相应的HO混合氰铜酸盐和Cu催化的有机镁试剂中，并且已经测试了这些物质对N-烷基-3-酰基吡啶鎓盐8和17的反应性。
• Stannylated phosphines I. Preparation of (β-trimethylstannyl)-alkyldiphenylphosphines
  作者：Terence N. Mitchell、Heinz-Joachim Belt

  DOI：10.1016/0022-328x(89)85311-2

  日期：1989.6