2-(吡啶-4-基)-5,6-二氢苯并[d]噻唑-7(4h)-酮 | 154404-90-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(吡啶-4-基)-5,6-二氢苯并[d]噻唑-7(4h)-酮
• 英文名称: 5,6-dihydro-2-(4-pyridyl)-7(4H)benzothiazolone
• 英文别名: 2-(pyridin-4-yl)-5,6-dihydrobenzo[d]thiazol-7(4H)-one；2-pyridin-4-yl-5,6-dihydro-4H-1,3-benzothiazol-7-one
• CAS: 154404-90-7
• 化学式: C₁₂H₁₀N₂OS
• mdl: MFCD16677191
• 分子量: 230.29
• InChiKey: UZMYBXRSPBYMMV-UHFFFAOYSA-N

物化性质

• 沸点：
  452.0±47.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934200090

反应信息

• 作为产物：
  描述：

  硫代异烟酰胺 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.25h， 生成 2-(吡啶-4-基)-5,6-二氢苯并[d]噻唑-7(4h)-酮
  参考文献：
  名称：

  A new heteroannulation method to 2-cyclohexenone, mediated by phosphonate auxiliaries. Synthesis of 4,5,6,7-tetrahydrobenzothiazole derivatives

  摘要：

  Dimethyl (1,2-epoxy-3-oxocyclohex-1-yl)phosphonate 7, easily available from 2-cyclohexen-1-one, affords the new (tetrahydrobenzothiazolyl)phosphonates 10 upon reaction with thiocarboxamides 8. This cyclocondensation proceeds with regioselective conjunction of the bis-nucleophile 8 to carbonyl group and adjacent oxirane carbon of the epoxide precursor. On treatment with alkali the 5,6-dihydro-7(4H)benzothiazolones 12 are obtained from compounds 10, or from the intermediately formed bicyclic dihydroxy derivatives 9. Reaction of the corresponding cyclopentylphosphonate 14 with thiobenzamide (8b) yields the cyclopentathiazole derivative 15 as a single isomer, the dihydro-thiazole moiety being now annulated regio- and cis-stereoselectively to both oxirane carbons of the epoxyphosphonate.

  DOI：

  10.1007/bf00817312

文献信息

• Versatile approaches to a library of building blocks based on 5-acylthiazole skeleton
  作者：Olesia G. Kulyk、Dmytro A. Biloborodov、Maksim A. Cherevatenko、Yevhen Y. Shyriakin、Alexander Yu. Lyapunov、Alexander V. Mazepa、Valerii V. Vashchenko、Valeriy D. Orlov、Maksim A. Kolosov

  DOI：10.1080/00397911.2020.1808224

  日期：2020.12.1

  Abstract Thiazole derivatives represent an important class of azole heterocycles with a broad spectrum of biological activity and, therefore, the synthesis of these compounds is of remarkable concern. We present here practical and reliable protocol for synthesis of some 5-acylthiazoles and demonstrate their utility in the preparation of several new series of thiazole-containing building blocks through

  摘要 噻唑衍生物是一类重要的唑类杂环，具有广泛的生物活性，因此，这些化合物的合成备受关注。我们在此介绍了一些实用且可靠的合成一些 5-酰基噻唑的方案，并展示了它们在通过 5-酰基功能的转化制备几个新系列的含噻唑结构单元中的效用。具体而言，噻唑基醇、肟、伯胺和仲胺以良好到极好的收率连续合成。所得化合物的化学结构经 1H 和 13C NMR 光谱、元素分析和质谱证实。图形概要
• A new heteroannulation method to 2-cyclohexenone, mediated by phosphonate auxiliaries. Synthesis of 4,5,6,7-tetrahydrobenzothiazole derivatives
  作者：E. �hler

  DOI：10.1007/bf00817312

  日期：——

  Dimethyl (1,2-epoxy-3-oxocyclohex-1-yl)phosphonate 7, easily available from 2-cyclohexen-1-one, affords the new (tetrahydrobenzothiazolyl)phosphonates 10 upon reaction with thiocarboxamides 8. This cyclocondensation proceeds with regioselective conjunction of the bis-nucleophile 8 to carbonyl group and adjacent oxirane carbon of the epoxide precursor. On treatment with alkali the 5,6-dihydro-7(4H)benzothiazolones 12 are obtained from compounds 10, or from the intermediately formed bicyclic dihydroxy derivatives 9. Reaction of the corresponding cyclopentylphosphonate 14 with thiobenzamide (8b) yields the cyclopentathiazole derivative 15 as a single isomer, the dihydro-thiazole moiety being now annulated regio- and cis-stereoselectively to both oxirane carbons of the epoxyphosphonate.