2-[(3,3,4,4-tetramethylthietan-2-ylidene)amino]phenol | 312313-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[(3,3,4,4-tetramethylthietan-2-ylidene)amino]phenol
• 英文别名: o-Hydroxy-N-(3,3,4,4-tetramethylthietan-2-ylidene)aniline
• CAS: 312313-52-3
• 化学式: C₁₃H₁₇NOS
• 分子量: 235.35
• InChiKey: SMYSQMQSCHWNRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  57.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(3,3,4,4-tetramethylthietan-2-ylidene)amino]phenol 以 甲苯 为溶剂， 反应 5.0h， 以100%的产率得到3-(benzoxazol-2-yl)-2,3-dimethylbutane-2-thiol
  参考文献：
  名称：

  N-酰基苯并恶唑-2-硫酮的光化学反应

  摘要：

  研究了N-酰基苯并恶唑-2-硫酮1的光化学反应。在多种存在下辐照N-酰基苯并恶唑-2-硫酮1烯烃 2产生2取代苯并恶唑 3–20和/或意想不到的产物，通过分子内诱捕亚氨基噻吨21–29酰基 经过 硫醇根阴离子两性离子中间体I和酚盐阴离子分别由区域选择性形成的螺环氨基硫杂环丁烷AT衍生的两性离子中间体II[2 + 2]环加成的碳硫双键1与烯烃 双键。

  DOI：

  10.1039/b002548h
• 作为产物：
  描述：

  methyl 2-thioxo-3H-benzoxazole-3-carboxylate 在 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 反应 2.0h， 生成 2-[(3,3,4,4-tetramethylthietan-2-ylidene)amino]phenol
  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

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.
• Photochemical reactions of N-acylbenzoxazole-2-thiones
  作者：Takehiko Nishio、Ikuo Iida、Kunio Sugiyama

  DOI：10.1039/b002548h

  日期：——

  presence of a variety of alkenes 2 yields 2-substituted benzoxazoles 3–20 and/or the unexpected products, iminothietanes 21–29 by intramolecular trapping of the acyl group by thiolate anion of the zwitterionic intermediate I and by the phenolate anion of the zwitterionic intermediate II, respectively, derived from the spirocyclic aminothietanes AT which are formed by regioselective [2+2] cycloaddition of

  研究了N-酰基苯并恶唑-2-硫酮1的光化学反应。在多种存在下辐照N-酰基苯并恶唑-2-硫酮1烯烃 2产生2取代苯并恶唑 3–20和/或意想不到的产物，通过分子内诱捕亚氨基噻吨21–29酰基 经过 硫醇根阴离子两性离子中间体I和酚盐阴离子分别由区域选择性形成的螺环氨基硫杂环丁烷AT衍生的两性离子中间体II[2 + 2]环加成的碳硫双键1与烯烃 双键。