19,20,21-trithiatetracyclo[14.2.1.1^3.6.1^9,12]heneicosa-4,6,10,12,16,18-hexaene | 65038-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 19,20,21-trithiatetracyclo[14.2.1.1^3.6.1^9,12]heneicosa-4,6,10,12,16,18-hexaene
• 英文别名: [2.2.2](2,5)Thiophenophane；19,20,21-trithiatetracyclo[14.2.1.14,7.110,13]henicosa-1(18),4,6,10,12,16-hexaene
• CAS: 65038-09-7
• 化学式: C₁₈H₁₈S₃
• 分子量: 330.539
• InChiKey: ZIWXCGMVOGUYLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,5-二亚甲基-2,5-二氢噻吩 以30%的产率得到
  参考文献：
  名称：

  Huang Chin-Shui, Peng Chun-Chieh, Chou Chin-Hsing, Tetrahedron Lett, 35 (1994) N 24, S 4175-4176

  摘要：

  DOI：

文献信息

• Fluoride-induced 1,6-elimination to p-quinodimethane. A new preparative method for [2.2]paracyclophane, [2.2](2.5)furanophane and [2.2](2.5)thiophenophane
  作者：Yoshihiko Ito、Satoru Miyata、Masashi Nakatsuka、Takeo Saegusa

  DOI：10.1021/jo00318a047

  日期：1981.2
• Oligomerization of the Thiophene-Based <i>p</i>-Quinodimethanes 2,5-Dimethylene-2,5-dihydrothiophene and 2-Ethylidene-5-methylene-2,5-dihydrothiophene
  作者：Walter S. Trahanovsky、Deborah Louise Miller、Yili Wang

  DOI：10.1021/jo961528i

  日期：1997.12.1

  Flash vacuum pyrolysis (FVP) of (5-methyl-2-thiophene-yl)methyl benzoate (8) produces in ca. 75% yield 2,5-dimethylene-2,3-dihydrothiophene, S-monomer (3). S-Monomer 3 is relatively stable dissolved in carbon disulfide-chloroform at -78 degrees C. The structure of 3 is confirmed by its spectral properties. When a 0.17 M solution of S-monomer 3 was allowed to warm to room temperature, SS-dimer 5 ([2,2](2,5)thiophenophane, 14.7%), SSS-trimer 7 ([2,2,2](2,5)thiophenophane, 44.3%), and polymer were produced. A small amount (<1%) of an SSSS-tetramer was detected by GC/MS. The mechanism proposed for the formation of these oligomers involves the combination of two molecules of 3 to give an intermediate diradical (11) that can close to form dimer 5 or react with additional molecules of 3 to form the higher oligomers. Evidence for the trapping of diradical 11 by 2,5-dimethylene-2,5-dihydrofuran (O-monomer 2) was obtained. Co-oligomerization of S-monomer 3 and O-monomer 2 gave four compounds containing the thiophene moiety: OS-dimer 16, SS-dimer 5, OSS-trimer 17, and SSS-trimer 7. Some OO-dimer 4 was produced but no 000-trimer 6 was observed and only a trace of OOS-trimer 18 was detected. Additional support for the diradical mechanism was obtained from the study of the oligomerization of the methyl derivatives of 3,2-ethylidene-5-methylene-2,5-dihydrothiophene (10, E and Z isomers), prepared by the FVP of (5-ethyl-2-thiophene-yl)methyl benzoate (9). Oligomerization of 10 gave several dimers and trimers including two acyclic dimers that are accounted for by intramolecular disproportionation.
• Reaction of 2,5-dimethylene-2,5-dihydrothiophene with triplet oxygen
  作者：Chin-Shui Huang、Chun-Chieh Peng、Chin-Hsing Chou

  DOI：10.1016/s0040-4039(00)73143-1

  日期：1994.6

  2,5-Dimethylene-2,5-dihydrothiophene (1), prepared by the pyrolysis of 5-methylthenyl benzoate (3), has been detected by low-temperature NMR spectroscopy. 1 reacts with triplet oxygen to form a cyclic bisperoxide 6. Upon heating, 6 decomposes to give 2,5-bis(hydroxymethyl)thiophene (7), 2-formyl-5-hydroxymelhylthiophene (8) and 2,5-diformylthiophene (9) in a ratio of 1:2:1, respectively.
• Huang Chin-Shui, Peng Chun-Chieh, Chou Chin-Hsing, Tetrahedron Lett, 35 (1994) N 24, S 4175-4176
  作者：Huang Chin-Shui, Peng Chun-Chieh, Chou Chin-Hsing

  DOI：——

  日期：——
• ITO YOSHIHIKO; MIYATA SATORU; NAKATSUKA MASASHI; SAEGUSA TAKEO, J. ORG. CHEM., 1981, 46, NO 5, 1043-1044
  作者：ITO YOSHIHIKO、 MIYATA SATORU、 NAKATSUKA MASASHI、 SAEGUSA TAKEO

  DOI：——

  日期：——