Trimethyl-phenanthren-9-yl-stannane | 957-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: Trimethyl-phenanthren-9-yl-stannane
• 英文别名: Trimethyl(phenanthren-9-yl)stannane
• CAS: 957-74-4
• 化学式: C₁₇H₁₈Sn
• 分子量: 341.04
• InChiKey: IVQQCKXNHQQXDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  Trimethyl-phenanthren-9-yl-stannane 在 水 作用下， 以 二氯甲烷 为溶剂， 生成 Phenanthrene-2-sulfonamide
  参考文献：
  名称：

  Tin for organic synthesis. 10. Unconventional regiospecific syntheses of aromatic carbonamides and thiocarbonamides by means of tin-mediated Friedel-Crafts reactions

  摘要：

  Friedel-Crafts reactions of stannylarenes 1 with tosyl isocyanate (TsNCO, 2) give N-tosylcarbonamides 3 via ipso substitution of the stannyl group. Thus, unconventionally substituted aromatic carbonamides can be obtained. The combination of the reaction of 1 and 2 with that of 1 and chlorosulfonyl isocyanate (14) allows one-pot syntheses of N-(arylsulfonyl)-substituted aromatic carbonamides with optional substitution patterns on both aromatic rings. The known ipso-specific substitutions of stannylarenes with 14 are extended to bi- and tricyclic arenes as well as to thiophenes 6 and 22. One stannyl group can serve as a leaving group for two aromatic systems, as shown with diaryldialkyltins 29. Also, stannylalkanes such as 27 react with 14 to afford alkylsulfonyl isocyanates and products of further reactions, such as 28. From the reactions of 1 with ethoxycarbonyl isothiocyanate (32), ortho- and meta-substituted aromatic thiocarbonamides 33 which are potential precursors for further syntheses, are accessible. The scope, limitations, and mechanism of these electrophilic substitutions are outlined.

  DOI：

  10.1021/jo00077a020
• 作为产物：
  描述：

  三甲基氯化锡 、 lithium,9H-phenanthren-9-ide 以 乙醚 为溶剂， 以40%的产率得到Trimethyl-phenanthren-9-yl-stannane
  参考文献：
  名称：

  Buchman, O.; Grosjean, M.; Nasielski, J., Bulletin des Societes Chimiques Belges, 1962, vol. 71, p. 467 - 472

  摘要：

  DOI：

文献信息

• Some group IVB derivatives of 1,6-methano[10]annulene. Synthesis, substituent effects and reactivity
  作者：William Kitching、Henry A. Olszowy、Inge Schott、William Adcock、D.P. Cox

  DOI：10.1016/0022-328x(86)80191-7

  日期：1986.8

  measure of the substituent effects exerted by metalloid-containing groups in this non-benzenoid aromatic system. Comparisons are made with the corresponding naphthalene and some anthracene derivatives. Protiodemetallations of a number of arylsilanes and -stannanes have been examined, and in protiodestannylation by CH3CO2H/dioxane at 27°C (an electrophilic aromatic substitution) the α- (or 2-) position of

  合成了1,6-甲基[10]环戊烯的某些IVB族衍生物，并记录和分配了它们的13 C核磁共振波谱，以测量这种非苯甲酸酯芳族化合物中含准金属的基团所产生的取代基作用。系统。与相应的萘和一些蒽衍生物进行了比较。已经研究了许多芳基硅烷和-锡烷基的金属丙酸酯化，并在27°C（亲电子芳族取代）下通过CH 3 CO 2 H /二恶烷进行金属甲酸酯化，在1,6-甲氧基的α-（或2-）位[ 10]环戊烯是约。反应活性是萘的α（或1-）位置的35倍，而在CF 3 CO 2 H / CH的丙硅烷基化中在27°C下3 CO 2 H约为。反应性高700倍。
• Niestroj, Michael; Lube, Andreas; Neumann, Wilhelm P., Chemische Berichte, 1995, vol. 128, # 6, p. 575 - 580
  作者：Niestroj, Michael、Lube, Andreas、Neumann, Wilhelm P.

  DOI：——

  日期：——
• Buchman, O.; Grosjean, M.; Nasielski, J., Helvetica Chimica Acta, 1964, vol. 47, p. 1695 - 1700
  作者：Buchman, O.、Grosjean, M.、Nasielski, J.

  DOI：——

  日期：——
• Buchman, O.; Grosjean, M.; Nasielski, J., Bulletin des Societes Chimiques Belges, 1963, vol. 72, p. 286 - 288
  作者：Buchman, O.、Grosjean, M.、Nasielski, J.

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.2, 1.1.2.1.12, page 146 - 152
  作者：

  DOI：——

  日期：——

表征谱图