2-isopropenyl-2-thiolene-1,1-dioxide | 4055-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢噻吩类
• 英文名称: 2-isopropenyl-2-thiolene-1,1-dioxide
• 英文别名: 5-Isopropenyl-2,3-dihydrothiophene 1,1-dioxide；5-prop-1-en-2-yl-2,3-dihydrothiophene 1,1-dioxide
• CAS: 4055-17-8
• 化学式: C₇H₁₀O₂S
• 分子量: 158.221
• InChiKey: FNFZPJUWRJJULU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-isopropenyl-2-thiolene-1,1-dioxide 在 silver(l) oxide 作用下， 以 氯仿 、 溶剂黄146 、 苯 为溶剂， 反应 18.0h， 生成 4-methyl-3,3,6,11-tetraoxo-7,10-methano-1,2,5,6,6a,7,10,10a,11,11b-decahydrothieno<3,2-a>anthracene
  参考文献：
  名称：

  Tolstikov, G. A.; Shul'ts, E. E.; Vafina, G. F., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 6.2, p. 1109 - 1121

  摘要：

  DOI：

文献信息

• Diels-alder reactions with cyclic sulfones: VIII. Organic catalysis in the synthesis of spiro[1-benzothiophene-4,5′-pyrimidine]-2′,4′,6′-trione 1,1-dioxides and 2′-thioxospiro[1-benzothiophene-4,5′-pyrimidine]-4′,6′-dione 1,1-dioxides
  作者：E. E. Shul’ts、G. N. Andreev、M. M. Shakirov、N. I. Komarova、I. Yu. Bagryanskaya、Yu. V. Gatilov、G. A. Tolstikov

  DOI：10.1134/s1070428009010126

  日期：2009.1

  from 2-methoxybenzaldehyde and thiobarbituric acid) in the presence of (−)-ephedrine or L-4-(tert-butyldimethylsiloxy) proline gave the corresponding 2-thioxospiro[1-benzothiophene-4,5′-pyrimidine]-4′,6′-dione 1,1-dioxide with an enantiomeric excess of 80%.

  5-异丙烯基-2,3-二氢噻吩1,1-二氧化物在手性胺或氨基酸存在下与5-亚甲基亚嘧啶-2,4,6-三酮和5-亚甲基-2-硫代嘧啶-4,6-二酮反应具有高的区域和立体选择性，可将在5位上稠合的巴比妥酸和硫代巴比妥酸的旋光衍生物衍生为1-苯并噻吩1,1-二氧化物片段。5-异丙烯基-2,3-二氢噻吩1,1-二氧化物与5-（2-甲氧基亚苄基）-2-硫代嘧啶-4,6-二酮（由2-甲氧基苯甲醛和硫代巴比妥酸原位生成）的反应（-）-麻黄碱或L-4-（叔丁基二甲基甲硅烷氧基）脯氨酸的混合物制得相应的2-thioxospiro [1-苯并噻吩-4,5'-嘧啶] -4'，6'-二酮1,1-二氧化物对映体过量80％。
• Diels–Alder Reactions with Cyclic Sulfones: VII. Synthesis of 1-Benzothiophene 1,1-Dioxide Derivatives
  作者：G. N. Andreev、E. E. Shul’ts、A. A. Volkov、M. M. Shakirov、I. Yu. Bagryanskaya、Yu. V. Gatilov、G. A. Tolstikov

  DOI：10.1023/b:rujo.0000044549.81561.4f

  日期：2004.6

  5-Arylmethylene-2,2-dimethyl-1,3-dioxane-4,6-diones reacted with 5-isopropenyl-2,3-dihydrothiophene 1,1-dioxide to give the corresponding ortho-addition products, 5-aryl-2',2',7-trimethyl-3,3a,5,6-tetrahydro-2H-spiro[1-benzothiophene-4,5'-[1,3]dioxane]-4',6'-dione 1,1-dioxides. Their aminolysis resulted in opening of the 1,3-dioxane ring and formation of 4-carbamoyl-7-methyl-2,3,3a,4,5,6-hexahydro-l-benzothiophene-4-carboxylic acid 1,1-dioxide whose structure was determined by X-ray analysis. Reactions of the spiro adducts with amines and hydrazine hydrate afforded the corresponding mono- or dicarboxylic acid monoamides (hydrazide).
• Synthetic transformations of higher terpenoids: XVIII. Synthesis of optically active 9,10-anthraquinone derivatives
  作者：E. E. Shul’ts、D. S. Oleinikov、I. V. Nechepurenko、M. M. Shakirov、G. A. Tolstikov

  DOI：10.1134/s1070428009010138

  日期：2009.1

  Retro-Diels-Alder decomposition of dodecahydro-endo-4b,12-ethenochrysene-1,4-diones obtained from a tricyclic diterpenoid, levopimaric acid, gave optically active 5-[2-(6-vinyl-2,6-dimethyl-2-carboxycyclohexyl) ethyl]-7-isopropyl-1,4-naphthoquinones which reacted with silyloxybutadienes to produce the corresponding 6- and 7-hydroxyanthraquinones, 5-furyl-7-hydroxytetrahydroanthraquinones, or 5-furyl-7-oxohexahydroanthraquinones. Condensation of the naphthoquinone derivatives with 5-isopropenyl-2,3-dihydrothiophene 1,1-dioxide resulted in the formation of 6,11-dioxodihydro- and 6,11-dioxohexahydroanthra[2,1-b]thiophene 3,3-dioxides. 6- and 7-Hydroxyanthraquinones were also obtained by reaction of dodecahydro-endo-4b,12-ethenochrysene-1,4-diones with Danishevsky diene, followed by cleavage of the polycyclic adducts. The cycloaddition of 5-[2-(-2-carboxy-2,6-dimethyl-6-vinylcyclohexyl)ethyl]-7-isopropyl-1,4-naphthoquinones in the presence of Lewis acids was characterized by increased regioselectivity.
• Diels-alder reaction with cyclic sulfones. 9.* Synthesis of 10-oxo-1h-tetrahydrofluo-reno[2,1-b]thiophene dioxides*2
  作者：E. E. Shults、G. N. Andreev、M. M. Shakirov、I. Yu. Bagryanskaya、G. A. Tolstikov

  DOI：10.1007/s10593-009-0174-1

  日期：2008.10

  The treatment of 5-aryl-4',6'-dioxo-2,3,3a,4,5,6-hexahydrospiro-[benzothiophene-4,5'-1,3-dioxane] 1,1-dioxides with boron trifluoride etherate in dichloroethane leads to the formation of products of intramolecular acylation, namely, the corresponding 10-oxo-1H-5,5a,10a,10b-tetrahydrofluoreno-[2,1-b]thiophene dioxides. In all cases, 5-aryl-4-carboxyhexahydrobenzo[b]thiophene 1,1-dioxides were also isolated. The product ratio depends on the structure of the aromatic substituent at C(5) of the spiro- adducts. The structure of 4-carboxy-5-(2-methoxyphenyl)-7-methyl -2,3,3a,4,5,6-hexahydro-benzo[b]thiophene 1,1-dioxide was confirmed by X-ray diffraction structural analysis.
• Synthesis and psychotropic properties of dihydro-, tetrahydronaphtho-, and anthraquinones, containing a heterocyclic fragment
  作者：T. G. Tolstikova、V. A. Davydova、É. É. Shul'ts、G. F. Vafina、G. M. Safarova、F. A. Zuridii、D. N. Lazareva、G. A. Tolstikov

  DOI：10.1007/bf00764992

  日期：1990.7