2-benzylaminocyclohepta-2,4,6-triene-1-thione | 3336-61-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-benzylaminocyclohepta-2,4,6-triene-1-thione
• 英文别名: 2-benzylamino-2,4,6-cycloheptatrienethione；2-Benzylamino-troponthion；2-(benzylamino)cyclohepta-2,4,6-triene-1-thione
• CAS: 3336-61-6
• 化学式: C₁₄H₁₃NS
• mdl: MFCD01858412
• 分子量: 227.33
• InChiKey: AFMWRWOWBIJIAH-UHFFFAOYSA-N

物化性质

• 熔点：
  138 °C
• 沸点：
  394.3±52.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  44.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯-4-甲基-1,3,5-三硝基苯 、 2-benzylaminocyclohepta-2,4,6-triene-1-thione 在 aluminum oxide 作用下， 以 氯仿 为溶剂， 以80%的产率得到
  参考文献：
  名称：

  摘要：

  Rreversible arrowL-Inversion of chiral spirocyclic and open-chain 2-arylaminotropone derivatives with varied heteroatom (O, S, N) has been studied. Kinetic relations holding in the R,L-permutation are discussed. Its mechanism includes formation and dissociation of spiro bonds and torsion stereodynamics.

  DOI：

  10.1023/a:1019619307779
• 作为产物：
  描述：

  2-benzylaminocyclohepta-2,4,6-trien-1-one 在 sodium sulfide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 生成 2-benzylaminocyclohepta-2,4,6-triene-1-thione
  参考文献：
  名称：

  摘要：

  Rreversible arrowL-Inversion of chiral spirocyclic and open-chain 2-arylaminotropone derivatives with varied heteroatom (O, S, N) has been studied. Kinetic relations holding in the R,L-permutation are discussed. Its mechanism includes formation and dissociation of spiro bonds and torsion stereodynamics.

  DOI：

  10.1023/a:1019619307779

文献信息

• Studies on Seven-membered Ring Compounds. XX. Reactions of Troponeimine Derivatives. (2)
  作者：Hideo Nakao、Nobuo Soma、Genshun Sunagawa

  DOI：10.1248/cpb.13.828

  日期：——

  The reaction of 2-methoxytroponeimine (I) and its N-methyl derivative (II) with active methylene compounds were carried out. The reaction of I with malononitrile, ethyl cyanoacetate or cyanoacetamide in the presence of sodium ethoxide afforded rearrangemet products, that is 3-phenylacrylic acid derivatives. The same reaction in the absence of sodium ethoxide gave mainly 2-imino-1, 2-dihydrocyclohepta[b]pyrrole derivatives. However, the reaction of I with diethyl malonate afforded ethyl 2-oxo-8-methoxy-1, 2-dihydrocyclohepta[b]pyrrole-3-carboxylate. II showed some different reactivity from I. Namely, the reaction of II with active methylene compounds in the presence of sodium ethoxide afforded 2-imino-1, 2-dihydrocyclohepta[b]pyrrole derivatives besides rearrangement products.

  2-甲氧基托品酮亚胺（I）及其N-甲基衍生物（II）与活性甲基酮化合物的反应进行了研究。I与丙二腈、氰乙酸乙酯或氰乙酰胺在乙醇钠存在下反应，得到了重排产物，即3-苯基丙烯酸衍生物。同样条件下，在无乙醇钠时主要生成2-亚胺基-1,2-二氢环庚[b]吡咯衍生物。然而，I与丙二酸二乙酯反应生成了乙酯2-氧代-8-甲氧基-1,2-二氢环庚[b]吡咯-3-羧酸酯。II显示出与I不同的反应活性，在乙醇钠存在下，II与活性甲基酮化合物的反应除了重排产物外，还主要生成2-亚胺基-1,2-二氢环庚[b]吡咯衍生物。
• Zwitterionic spirocycles based on dinitrobenzofurazan and tropolone heteroanalogs
  作者：A. V. Tkachuk、S. V. Kurbatov、O. N. Burov、M. E. Kletskii、Yu. P. Tavunova、P. G. Morozov、V. A. Voronina、V. I. Minkin

  DOI：10.1134/s1070428013090248

  日期：2013.9

  Zwitterionic spirocyclic sigma-complexes were synthesized by reaction of 7-chloro-4,6-dinitrobenzofurazan with 2-(benzylamino)cyclohepta-2,4,6-trien-1-one, 2-(benzylamino)cyclohepta-2,4,6-triene-1-thione, and N-benzyl-7-(benzylimino)cyclohepta-1,3,5-trien-1-amine. The structure, stereodynamics, and stability of the spirocycles were studied by NMR spectroscopy, X-ray analysis, and DFT quantum chemical calculations at the B3LYP/6-31G** level of theory. The contribution of heteroatoms to positive charge delocalization and the thermodynamic and kinetic stabilities of the spirocycles increase in the series aminotropone < aminothiotropone < aminotropone imine.
• Dipolar spirocyclic σ-complexes based on of 4,6-dinitrobenzofuroxan
  作者：S. V. Kurbatov、Z. N. Budarina、G. S. Vaslyaeva、N. I. Borisenko、A. P. Knyazev、V. I. Minkin、Yu. A. Zhdanov、L. P. Olekhnovich

  DOI：10.1007/bf02505683

  日期：1997.8

  The first dipolar spiro-sigma-complexes with a superelectrophilic dinintrobenzofuroxan fragment and tropolone systems with diastereotopic substituents were synthesized. The kinetics of their enantiotopomerization, which occurs via cleavage-formation of the C-spiro-heteroatom bond, was studied by dynamic H-1 NMR. The stereorigidity of dinitrobenzofuroxan spiro-complexes in this degenerated process increases in the series: tropolone < aminotropone << aminothiotropone approximate to aminotroponimine. The two last possess the highest kinetic stability compared to all known zwitterionic spiro-complexes.
• ——
  作者：L. P. Olekhnovich、Z. N. Budarina、G. S. Borodkin、S. V. Kurbatov、G. S. Vaslyaeva、Yu. A. Zhdanov

  DOI：10.1023/a:1019619307779

  日期：——

  Rreversible arrowL-Inversion of chiral spirocyclic and open-chain 2-arylaminotropone derivatives with varied heteroatom (O, S, N) has been studied. Kinetic relations holding in the R,L-permutation are discussed. Its mechanism includes formation and dissociation of spiro bonds and torsion stereodynamics.