3-(3,5-dichloro-2,4,6-trimethyl-phenyl)-(3ar,8bc)-3a,8b-dihydro-benzo[4,5]thieno[2,3-d]isoxazole | 63447-22-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(3,5-dichloro-2,4,6-trimethyl-phenyl)-(3ar,8bc)-3a,8b-dihydro-benzo[4,5]thieno[2,3-d]isoxazole
• 英文别名: 3-(3,5-dichloro-2,4,6-trimethylphenyl)-3a,8b-dihydro-[1]benzothiolo[2,3-d][1,2]oxazole
• CAS: 63447-22-3
• 化学式: C₁₈H₁₅Cl₂NOS
• 分子量: 364.295
• InChiKey: LKJMDYJOJNWHRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3,5-Dichloro-2,4,6-trimethyl-benzonitrile N-oxide 、 苯并噻吩 生成 3-(3,5-dichloro-2,4,6-trimethyl-phenyl)-(3ar,8bc)-3a,8b-dihydro-benzo[4,5]thieno[2,3-d]isoxazole
  参考文献：
  名称：

  BELTRAME P. L.; CATTANIA M. G.; REDAELLI V.; ZECCHI G., J. CHEM. SOC. PERKIN TRANS, 1977, PART 2, NO 5, 706-710

  摘要：

  DOI：

文献信息

• Rate enhancement of 1,3-dipolar cycloaddition ofN-methylindole: the singular role of Grignard reagents
  作者：Tiziana Benincori、Franco Sannicol�、Licia Trimarco、Laura Bonati、Stefania Grandi、Demetrio Pitea、Carlo Gatti

  DOI：10.1002/(sici)1099-1395(199807)11:7<455::aid-poc998>3.0.co;2-5

  日期：1998.7

  The reactions of 2-N-methylindolyl and 2- and 3-benzo[b]thiophenyl anions with nitrile oxides and nitrilimines were performed in order to investigate whether the use of anionic dipolarophiles modifies a classical 1,3-dipolar cycloaddition. When lithium compounds were used as bases, the heterocyclic anions invariably acted as nucleophilic species; in contrast, when a Grignard reagent was employed, the N-methylindole gave cycloaddition products with an extraordinary rate enhancement. The hypothesis that N-methylindole and ethylmagnesium bromide give an adduct much more reactive than N-methylindole itself was supported by the results of a theoretical investigation. The structure and electron distribution of the adduct were determined by ab initio calculations and compared with those of known Grignard complexes with nitrogen ligands. The performance of different basis sets was tested. The quantum theory of atoms in molecules was used to determine atomic charges and to describe the nature of bonds in terms of the properties of the electron density at the bond critical points. (C) 1998 John Wiley & Sons, Ltd.