8-(quinolyl)trimethylstannane | 73038-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-(quinolyl)trimethylstannane
• 英文别名: (quinolin-8-yl)trimethyltin(IV)；Trimethyl(quinolin-8-yl)stannane
• CAS: 73038-04-7
• 化学式: C₁₂H₁₅NSn
• 分子量: 291.968
• InChiKey: LSCCTULCHRKTPD-UHFFFAOYSA-N

物化性质

• 沸点：
  1 °C(Press: 0.4 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-(quinolyl)trimethylstannane 以 甲苯 为溶剂， 反应 2.0h， 生成 dichloropyridinyl(quinolin-8-yl)gallium(III)
  参考文献：
  名称：

  Ga / N Lewis对存在下的二氯甲烷，氯仿和氯二苯甲烷的脱氢脱氯

  摘要：

  Transmetalation occurs upon addition of GaCl3 to (quinolin-8-yl)trimethylstannane. The compound dissolves immediately in pyridine, and recrystallization gives dichloropyridinyl(quinolin-8-yl)gallium(III). In chloroform, the compound bis-mu-(quinolin-8-y1)-mu-chloro-dichlorodigallium(III) tetrachloro-gallate could be isolated in small quantities; however, the major product was trichloro(quinolinium-8-yl)gallate(III) zwitterion. The zwitterion also formed upon addition of methylene chloride or chlorodiphenylmethane. We hypothesize that the highly electrophilic digallyl cation abstracts chloride to form a carbocation and that proton transfer from the carbocation to the quinoline nitrogen affords transient carbenes. In particular, diphenyl carbene forms from dehydrodechlorination of chlorodiphenylmethane in toluene/cyclohexene to give a well-defined mixture of products due to cyclopropanation and C-H insertion reactions. Dichloropyridinyl(quinolin-8-yl)gallium(III) undergoes reaction with chloroform only at elevated temperature to yield quinolinium tetrachlorogallate salt as the product. This salt also forms in the reaction of chloroform with GaCl3 and quinoline at elevated temperature. The zwitterion could be converted to quinolinium tetrachlorogallate upon heating, which supports the idea that it was formed initially as an intermediate. Thus, the Ga/N Lewis pairs appear capable of dehydrodechlorination of chloroalkanes.

  DOI：

  10.1021/acs.organomet.6b00867
• 作为产物：
  描述：

  8-碘喹啉 、 三甲基氯化锡 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 18.5h， 以66.2%的产率得到8-(quinolyl)trimethylstannane
  参考文献：
  名称：

  Preparation of RHgCl via transmetalation of (8-quinolyl)SnMe₃and redistribution to R₂Hg (R = 8-quinolyl): a highly distorted diorganomercury(ii) with 84 degree C–Hg–C angle

  摘要：

  在将HgCl2添加到(8-喹啉基)SnMe3中时会发生过渡金属化反应，生成(8-喹啉基)HgCl。该分子具有惰性Hg-N路易斯对；然而，汞(II)中心对硫路易斯碱、S8或噻吩的亲和力较低。在NH4SCN的存在下，配体的重新分布导致R2Hg的形成。根据重结晶溶剂的不同，该分子可以呈线性或弯曲多晶型。弯曲多晶型中Hg(II)的几何结构是扭曲的三棱柱，其C-Hg-C角为84°，分子内Hg-N接触较弱，分子间存在两个η2-喹啉接触，相邻的R2Hg分子作为双η2-双齿配体参与其中。

  DOI：

  10.1039/c4dt00384e

文献信息

• SUGGS J. W.; PEARSON G. D. N., J. ORG. CHEM., 1980, 45, NO 8, 1514-1515
  作者：SUGGS J. W.、 PEARSON G. D. N.

  DOI：——

  日期：——
• ECHAVARREN, ANTONIO M.;STILLE, J. K., J. AMER. CHEM. SOC., 109,(1987) N 18, 5478-5486
  作者：ECHAVARREN, ANTONIO M.、STILLE, J. K.

  DOI：——

  日期：——