methyl 3',3',4',4'-tetramethylspiro[3H-benzoxazole-2,2'-thiethane]-3-carboxylate | 230958-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑啉
• 英文名称: methyl 3',3',4',4'-tetramethylspiro[3H-benzoxazole-2,2'-thiethane]-3-carboxylate
• 英文别名: Methyl 2',2',3',3'-tetramethylspiro[1,3-benzoxazole-2,4'-thietane]-3-carboxylate
• CAS: 230958-81-3
• 化学式: C₁₅H₁₉NO₃S
• 分子量: 293.387
• InChiKey: NPWDNACYMPDJSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3',3',4',4'-tetramethylspiro[3H-benzoxazole-2,2'-thiethane]-3-carboxylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 S-3-(1,3-Benzoxazol-2-yl)-2,3-dimethylbutan-2-yl thioacetate
  参考文献：
  名称：

  Photocycloaddition Reactions of Alkyl and Aryl 2-Thioxo-3H-benzoxazole- 3-carboxylates to Alkenes

  摘要：

  The photochemical reactions of alkyl and aryl 2-thioxo-3H-benzoxazole-3-carboxylates 1 have been examined. Irradiation of 1 in the presence of tetra- and trisubstituted alkenes 2a and 2b, 2-methylprop-2-ene nitrile 2e, and dienes 2f and 2g gave [2+2] cycloadducts of the C=S bond of 2-thioxobenzoxazoles and the C=C bond of alkenes, spiro[benzoxazole-thietanes] 3, 4, 8-13, 15, 18, 20, 23-26 in moderate-to-good yields. The photoaddition reactions proceed in a regiospecific manner. The spirocyclic compounds obtained are indefinitely stable at room temperature. Irradiation of la in the presence of 1,1- and 1,2-disubstituted alkenes 2c and 2d yielded the products 5-7 of oxazole-ring cleavage. Compound 1d also underwent photoaddition with alkenes to yield spiro[benzoxazole-thietanes] and/or 2-substituted benzoxazoles and/or iminothietanes, depending on the nature of the substituents present in the alkenes. On intramolecular [2 + 2] photoadduct, tetracyclic 27, was obtained, when ethenyl 2-thioxobenzoxazole-3-carboxylate 1e was irradiated.

  DOI：

  10.1002/1522-2675(200208)85:8<2383::aid-hlca2383>3.0.co;2-e
• 作为产物：
  描述：

  2,3-二甲基-2-丁烯 、 methyl 2-thioxo-3H-benzoxazole-3-carboxylate 以 苯 为溶剂， 以50%的产率得到methyl 3',3',4',4'-tetramethylspiro[3H-benzoxazole-2,2'-thiethane]-3-carboxylate
  参考文献：
  名称：

  Photocycloaddition of N-alkoxycarbonylbenzoxazole-2-thiones to alkenes: isolation of stable aminothietanes

  摘要：

  N-烷氧基和N-芳氧基酰基苯并恶唑-2-硫酮1在光引发下与烯烃2发生区域选择性的光环加成反应，以中等至高产率生成稳定的螺环氨基噻吩3-4、7-9和11。

  DOI：

  10.1039/a900699k

文献信息

• Photocycloaddition Reactions of Alkyl and Aryl 2-Thioxo-3H-benzoxazole- 3-carboxylates to Alkenes
  作者：Takehiko Nishio、Kiyoko Shiwa、Masami Sakamoto

  DOI：10.1002/1522-2675(200208)85:8<2383::aid-hlca2383>3.0.co;2-e

  日期：2002.8

  The photochemical reactions of alkyl and aryl 2-thioxo-3H-benzoxazole-3-carboxylates 1 have been examined. Irradiation of 1 in the presence of tetra- and trisubstituted alkenes 2a and 2b, 2-methylprop-2-ene nitrile 2e, and dienes 2f and 2g gave [2+2] cycloadducts of the C=S bond of 2-thioxobenzoxazoles and the C=C bond of alkenes, spiro[benzoxazole-thietanes] 3, 4, 8-13, 15, 18, 20, 23-26 in moderate-to-good yields. The photoaddition reactions proceed in a regiospecific manner. The spirocyclic compounds obtained are indefinitely stable at room temperature. Irradiation of la in the presence of 1,1- and 1,2-disubstituted alkenes 2c and 2d yielded the products 5-7 of oxazole-ring cleavage. Compound 1d also underwent photoaddition with alkenes to yield spiro[benzoxazole-thietanes] and/or 2-substituted benzoxazoles and/or iminothietanes, depending on the nature of the substituents present in the alkenes. On intramolecular [2 + 2] photoadduct, tetracyclic 27, was obtained, when ethenyl 2-thioxobenzoxazole-3-carboxylate 1e was irradiated.
• Photocycloaddition of N-alkoxycarbonylbenzoxazole-2-thiones to alkenes: isolation of stable aminothietanes
  作者：Takehiko Nishio

  DOI：10.1039/a900699k

  日期：——

  N-Alkoxy- and N-aryloxycarbonylbenzoxazole-2-thiones 1 undergo photocycloaddition with alkenes 2 in a regiospecific manner to yield stable spirocyclic aminothietanes 3–4, 7–9 and 11 in fair to high yields.

  N-烷氧基和N-芳氧基酰基苯并恶唑-2-硫酮1在光引发下与烯烃2发生区域选择性的光环加成反应，以中等至高产率生成稳定的螺环氨基噻吩3-4、7-9和11。