3-Benzyloxycarbonylbenzoxazoline-2-thione | 91285-91-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Benzyloxycarbonylbenzoxazoline-2-thione
• 英文别名: N-(benzyloxycarbonyl)benzoxazoline-2-thione；benzyl 2-thioxo-3H-benzoxazole-3-carboxylate；benzyl 2-thioxobenzo[d]oxazol-3(2H)-carboxylate；3(2H)-Benzoxazolecarboxylic acid, 2-thioxo-, phenylmethyl ester；benzyl 2-sulfanylidene-1,3-benzoxazole-3-carboxylate
• CAS: 91285-91-5
• 化学式: C₁₅H₁₁NO₃S
• 分子量: 285.323
• InChiKey: ZAHQFDKPAWTAOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  417.9±38.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  3-Benzyloxycarbonylbenzoxazoline-2-thione 在 sodium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 N-benzyloxycarbonyl-L-phenylalanylglycine methyl ester
  参考文献：
  名称：

  On the Use of Five-Membered Heterocycles in Peptide Chemistry*

  摘要：

  提出了使用2-苯并噁唑硫醇、2-苯并噻唑硫醇和2-苯并咪唑硫醇的N-酰基衍生物，它们既可作为高效的酰化剂用于合成N-苄氧羰基和N-芴甲氧羰基氨基酸衍生物，也可作为活性酰胺用于合成肽。

  DOI：

  10.1055/s-1985-31329
• 作为产物：
  描述：

  氯甲酸苄酯 、 2-巯基苯并恶唑 在 sodium carbonate 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以89%的产率得到3-Benzyloxycarbonylbenzoxazoline-2-thione
  参考文献：
  名称：

  On the Use of Five-Membered Heterocycles in Peptide Chemistry*

  摘要：

  提出了使用2-苯并噁唑硫醇、2-苯并噻唑硫醇和2-苯并咪唑硫醇的N-酰基衍生物，它们既可作为高效的酰化剂用于合成N-苄氧羰基和N-芴甲氧羰基氨基酸衍生物，也可作为活性酰胺用于合成肽。

  DOI：

  10.1055/s-1985-31329

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.
• 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).
• On the Use of Five-Membered Heterocycles in Peptide Chemistry*
  作者：S. ROMANI、L. MORODER、G. BOVERMANN、E. WÜNSCH

  DOI：10.1055/s-1985-31329

  日期：——

  N-Acyl derivatives of 2-benzoxaolethiol, 2-benzothiazolethiol and 2-benzimidazolethiol are proposed for use both as efficient acylating agents for the synthesis of N-benzyloxycarbonyl and N-fluorenylmethyloxycarbonyl amino acid derivatives and as activated amides for the synthesis of peptides.

  提出了使用2-苯并噁唑硫醇、2-苯并噻唑硫醇和2-苯并咪唑硫醇的N-酰基衍生物，它们既可作为高效的酰化剂用于合成N-苄氧羰基和N-芴甲氧羰基氨基酸衍生物，也可作为活性酰胺用于合成肽。
• Design of benzimidazole- and benzoxazole-2-thione derivatives as inhibitors of bacterial hyaluronan lyase
  作者：Stephan Braun、Alexander Botzki、Sunnhild Salmen、Christian Textor、Günther Bernhardt、Stefan Dove、Armin Buschauer

  DOI：10.1016/j.ejmech.2011.07.014

  日期：2011.9

  Bacterial hyaluronan lyases (Hyal) degrade hyaluronan, an important component of the extracellular matrix, and are involved in microbial spread. Hyal inhibitors may serve as tools to study the role of the enzyme, its substrates and products in the course of bacterial infections. Moreover, such enzyme inhibitors are potential candidates for antibacterial combination therapy. Based on crystal structures of Streptococcus pneumoniae Hyal in complex with a hexasaccharide substrate and with different inhibitors, 1-acylated benzimidazole-2-thiones and benzoxazole-2-thiones were derived as new leads for the inhibition of Streptococcus agalactiae strain 4755 Hyal. Structure-based optimization led to N-(3-phenylpropionyl)benzoxazole-2-thione, one of the most potent compounds known to date (IC50 values: 24 mu M at pH 7.4, 15 mu M at pH 5). Among the 27 new derivatives, other N-acylated benzimidazoles and benzoxazoles are just as active at pH 7.4, but not at pH 5. The results support a binding mode characterized by interactions with residues in the catalytic site and with a hydrophobic patch. (C) 2011 Elsevier Masson SAS. All rights reserved.