prop-2-enyl 2-thioxo-3H-benzoxazole-3-carboxylate | 49740-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: prop-2-enyl 2-thioxo-3H-benzoxazole-3-carboxylate
• 英文别名: N-(allyloxycarbonyl)benzoxazoline-2-thione；allyl 2-thioxo-1,3-benzoxazole-3(2H)-carboxylate；prop-2-enyl 2-sulfanylidene-1,3-benzoxazole-3-carboxylate
• CAS: 49740-42-3
• 化学式: C₁₁H₉NO₃S
• 分子量: 235.263
• InChiKey: TXDKOXJVFXPRPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  prop-2-enyl 2-thioxo-3H-benzoxazole-3-carboxylate 以 甲苯 、 苯 为溶剂， 生成 prop-2-enyl 2-[(3,3,4,4-tetramethylthietan-2-ylidene)amino]phenyl carbonate
  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：

  氯甲酸烯丙酯 、 2-巯基苯并恶唑 在 sodium hydride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 1.0h， 以95%的产率得到prop-2-enyl 2-thioxo-3H-benzoxazole-3-carboxylate
  参考文献：
  名称：

  Acylation and Alkoxycarbony-lation of Benzoxazoline-2-thione and Benzothiazoline-2-thione

  摘要：

  Acylation of benzoxazoline-2-thione (1) and benzothiazoline-2-thione (2) with acetic anhydride (3) and acyl chlorides (4) gave N-acyl (5, 6) and/or S-acyl (7, 8) derivatives depending on the nature of acylating agents and bases used. Alkoxycarbonylation of 1 with aralkyl chlorocarbonates (9) gave N-alkoxycarbonyl derivatives (10) mainly, while that of 2 with aralkyl chloroccarbonates (9) gave S-alkoxycarbonyl derivatives (12) exclusively. Photolysis of N-acyl derivatives (5 or 6) in the presence of alcohols afforded 1 or 2, respectively, together with esters (16).

  DOI：

  10.3987/com-03-s(p)10

文献信息

• Photoaddition Reactions of Benzoxazole-2(3H)-thiones to Cycloalkenes and Heteroaromatics
  作者：Takehiko Nishio、Kiyoko Shiwa、Masami Sakamoto

  DOI：10.1002/hlca.200390266

  日期：2003.10

  cyclohexa-1,4-diene (2d), and indene (2e) yielded 2-substituted benzoxazoles 4–13, 18 and 19, and iminothietanes 14–17, by intramolecular trapping of the acyl or MeOCO and PhOCO groups by thiolate anion of the zwitterionic intermediate I and by the phenolate anion of the zwitterionic intermediate II, respectively, derived from the spirocyclic amino-thietanes AT formed by [2+2] cycloaddition of the CS bond of

  苯并恶唑-2-硫酮的光加成反应1与环烯烃2和杂芳族化合物3进行了检查。的照射Ñ -acylbenzoxazole -2-硫酮1A和1B，和3-（甲氧羰基） -苯并恶唑-2-和3-（苯氧基羰基）（3 ħ）-thiones（1F和1H。，RESP）在环烯烃的存在2A -图2c，环己-1,4-二烯（2D）和茚（2E），得到2-取代的苯并恶唑4 - 13，18和19，和iminothietanes 14- 17，由两性离子中间体的硫醇盐阴离子的酰基或MeOCO和PhOCO基团的分子内俘获我和由两性离子中间体的酚盐阴离子II，分别从螺环氨基thietanes衍生AT通过形成[2 + 2] 1的CS键和2的CC键的环加成。在杂芳族化合物3的存在下照射1只能得到2-取代的苯并恶唑20 – 33。
• 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.
• Acylation and Alkoxycarbony-lation of Benzoxazoline-2-thione and Benzothiazoline-2-thione
  作者：Takehiko Nishio、Kiyoko Shiwa

  DOI：10.3987/com-03-s(p)10

  日期：——

  Acylation of benzoxazoline-2-thione (1) and benzothiazoline-2-thione (2) with acetic anhydride (3) and acyl chlorides (4) gave N-acyl (5, 6) and/or S-acyl (7, 8) derivatives depending on the nature of acylating agents and bases used. Alkoxycarbonylation of 1 with aralkyl chlorocarbonates (9) gave N-alkoxycarbonyl derivatives (10) mainly, while that of 2 with aralkyl chloroccarbonates (9) gave S-alkoxycarbonyl derivatives (12) exclusively. Photolysis of N-acyl derivatives (5 or 6) in the presence of alcohols afforded 1 or 2, respectively, together with esters (16).