N-Isopropylacetonitrilium hexachloroantimonate | 20126-93-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-Isopropylacetonitrilium hexachloroantimonate
• CAS: 20126-93-6
• 化学式: C₅H₁₀N*Cl₆Sb
• 分子量: 418.609
• InChiKey: ASSKWDRTDMIMSC-UHFFFAOYSA-H

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  4.36
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  降冰片烯 、 N-Isopropylacetonitrilium hexachloroantimonate 以 二氯甲烷 为溶剂， 反应 48.0h， 以91%的产率得到1,3,3-trimethyl-1-[(1RS,2RS,4SR)-8,9,10-trinorbornyl-2]-2-azoniaallene hexachloroantimonate
  参考文献：
  名称：

  Ene Reactions and [2+2]Cycloadditions of Nitrilium Salts with Alkenes

  摘要：

  N-Alkylnitrilium salts (1) undergo ene reactions with electron-rich di-and higher substituted alkenes 2 to afford either 2-azoniaallene salts (3, 6, 9, 11) (the nitrilium salt reacting as ene and the alkene reacting as enophile) or 1-azonia-1,4-pentadiene salts (10, 12) (the alkene reacting as ene and the nitrilium salt reacting as enophile). Competing with ene reactions tri-and tetrasubstituted alkenes and N-alkylnitrilium salts undergo [2+2]cycloaddition to furnish azetinium salts (8, 13). In solution, alkyl substituted 2-azoniaallene salts tautomerize to 2-azonia-1,3-butadiene salts (4, 5, 7). The constitutions of the 2-azoniaallene salt 6c and the azetinium salt 8 were secured by X-ray crystallographic analyses.

  DOI：

  10.1002/prac.199733901110
• 作为产物：
  描述：

  2-氯丙烷 、 乙腈 在 hexachloroantimonate(1-) 作用下， 生成 N-Isopropylacetonitrilium hexachloroantimonate
  参考文献：
  名称：

  Jochims, Johannes C.; Abu-El-Halawa, Rajab; Jibril, Ibrahim, Chemische Berichte, 1984, vol. 117, # 5, p. 1900 - 1912

  摘要：

  DOI：

文献信息

• Synthesis of N-Acyliminium Salts by Reaction of Nitrilium Salts with Ketones
  作者：Mahmoud Al-Talib、Magdi Zaki、Sabine Hehl、Rüdiger Stumpf、Helmut Fischer、Johannes C. Jochims

  DOI：10.1055/s-1996-4340

  日期：1996.9

  A new method for the preparation of N-acyliminium salts 3a-ab by reaction of nitrilium salts 1 with non-enolizable alkyl and aryl ketones 2 is described. Ketones without electron-releasing substituents react only with N-arylnitrilium salts 1. An X-ray structural analysis was carried out for the N-acyliminium salt 3j. From variable temperature NMR spectroscopy intramolecular conformational changes (essentially rotation around the iminium C=N double bond, coupled to rotation about the amide C-N single bond) of few compounds 3 were determined. The observed barriers to hindered rotation are compared with barriers calculated by the AM1 method.

  描述了一种通过氰镎盐1与非烯醇化烷基和芳基酮2反应制备N-酰亚胺正离子3a-ab的新方法。不含电子释放取代基的酮仅与N-芳基氰镎盐1反应。对N-酰亚胺正离子3j进行了X射线结构分析。通过变温核磁共振光谱，确定了少数化合物3的分子内构象变化（主要是围绕亚胺C=N双键的旋转，与酰胺C-N单键的旋转耦合）。实验观察到的旋转能垒与AM1方法计算的能垒进行了比较。
• On the Reaction of<i>N</i>-Alkylnitrilium Salts with Acetylenes: A New Synthesis of 2-Azoniaallene Salts
  作者：Rajab Abu-El-Halawa、Johannes C. Jochims

  DOI：10.1055/s-1992-26249

  日期：——

  N-alkylnitrilium hexachloroantimonates 1 react with phenylacetylene (2a) or bis(methylthio)acetylene (2f) to give 3-azonia-2,3,5-hexatriene hexachloroantimonates 4, which either enolize to furnish 4-alkylidene-2-methyl-6-phenyl-3-azonia-2,4-hexadiene salts 7d,e or cyclize to afford 3,4-bis(methylthio)-2H-pyrrolium salts 6f-k.

  N-烷基硝基六氯锑酸盐 1 与苯乙炔 (2a) 或双(甲硫基)乙炔 (2f) 反应，生成 3-氮杂-2,3,5-己二烯六氯锑酸盐 4，后者或者烯醇化生成 4-亚烷基-2-甲基-6-苯基-3-氮杂-2,4-己二烯盐 7d,e，或者环化生成 3,4-双(甲硫基)-2H-吡咯盐 6f-k。
• Reactions of Nitrilium Salts with α,β-Unsaturated Carbonyl Compounds
  作者：Johannes C. Jochims、Rajab Abu-El-Halawa、Michael O. Glocker、Laszlo Zsolnai、Gottfried Huttner

  DOI：10.1055/s-1990-27008

  日期：——

  Nitrilium salts 1 react with α,β-unsaturated ketones 7a and aldehydes 7f,h,j to furnish either 4H-1,3-oxazinium salts 5a-e or 6H-1,3-oxazinium salts 11f-i or N-acyl-1-azonia-1,3- butadiene salts 10j,k. The formation of these products is explained by a multistep reaction sequence starting with a [2+2] cycloaddition of the carbonyl double bond to the nitrilium triple bond. The constitution of 6H-1,3-oxazinium hexachloroantimonate 11i is confirmed by an X-ray structural analysis.

  硝盐 1 与 α,β-不饱和酮 7a 和醛 7f,h,j 反应，生成 4H-1,3-恶嗪盐 5a-e 或 6H-1,3-恶嗪盐 11f-i 或 N-酰基-1-azonia-1,3-丁二烯盐 10j,k。这些产物的形成可以通过多步反应顺序来解释，该反应顺序以羰基双键与腈鎓三键的[2+2]环加成开始。通过X射线结构分析确认了6H-1,3-恶嗪鎓六氯锑酸盐11i的构成。
• Glocker, Michael O.; Shrestha-Davadi, Prativa Bade; Kuechler-Krischun, Jonna, Chemische Berichte, 1993, vol. 126, # 8, p. 1859 - 1866
  作者：Glocker, Michael O.、Shrestha-Davadi, Prativa Bade、Kuechler-Krischun, Jonna、Hofmann, Josef、Fischer, Helmut、Jochims, Johannes C.

  DOI：——

  日期：——
• Sheradsky, Tuvia; Nov, Eliahu, Journal of the Chemical Society. Perkin transactions I, 1983, # 3, p. 527 - 530
  作者：Sheradsky, Tuvia、Nov, Eliahu

  DOI：——

  日期：——