2-苯基-5,6-二氢苯并[d]噻唑-7(4h)-酮 | 17583-15-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-苯基-5,6-二氢苯并[d]噻唑-7(4h)-酮
• 中文别名: 2-苯基-5,6-二氢苯并[D]噻唑-7(4H)-酮
• 英文名称: 5,6-dihydro-2-phenyl-7(4H)benzothiazole
• 英文别名: 2-phenyl-5,6-dihydrobenzo[d]thiazol-7(4H)-one；2-Phenyl-7-oxo-4,5,6,7-tetrahydro-benzothiazol；2-Phenyl-7-oxo-4,5,6,7-tetrahydro-benzthiazol；2-phenyl-5,6-dihydro-4H-benzothiazol-7-one；2-phenyl-5,6-dihydro-4H-1,3-benzothiazol-7-one
• CAS: 17583-15-2
• 化学式: C₁₃H₁₁NOS
• mdl: MFCD14705873
• 分子量: 229.302
• InChiKey: LDXLKSGOQIQGLG-UHFFFAOYSA-N

物化性质

• 沸点：
  414.2±48.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934200090

反应信息

• 作为反应物：
  描述：

  2-苯基-5,6-二氢苯并[d]噻唑-7(4h)-酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以90%的产率得到2-phenyl-4,5,6,7-tetrahydrobenzo[d]thiazol-7-ol
  参考文献：
  名称：

  基于 5-酰基噻唑骨架的构建块库的通用方法

  摘要：

  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

  DOI：

  10.1080/00397911.2020.1808224
• 作为产物：
  描述：

  dimethyl <(4,5,6,7-tetrahydro-7-hydroxy-2-phenyl)benzothiazol-7-yl>phosphonate 在 sodium hydroxide 作用下， 反应 0.33h， 以95%的产率得到2-苯基-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

• BICYCLIC THIAZOLES AS ALLOSTERIC MODULATORS OF MGLUR5 RECEPTORS
  申请人：MacDonald Gregor James

  公开号：US20120252800A1

  公开（公告）日：2012-10-04

  The present invention relates to novel bicyclic thiazoles which are positive allosteric modulators of the metabotropic glutamate receptor subtype 5 (“mGluR5”) and which are useful for the treatment or prevention of disorders associated with glutamate dysfunction and diseases in which the mGluR5 subtype of receptors is involved. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes for preparing such compounds and compositions, and to the use of such compounds and compositions for the prevention and treatment of disorders in which mGluR5 is involved.

  本发明涉及新型的双环噻唑，它们是代谢型谷氨酸受体亚型5（“mGluR5”）的阳性别构调节剂，可用于治疗或预防与谷氨酸功能障碍有关的疾病以及涉及mGluR5受体亚型的疾病。该发明还涉及包含这种化合物的药物组合物，制备这种化合物和组合物的方法，以及利用这种化合物和组合物预防和治疗涉及mGluR5的疾病的用途。
• Lehmann,G. et al., Zeitschrift fur Chemie, 1967, vol. 7, p. 422
  作者：Lehmann,G. et al.

  DOI：——

  日期：——
• A‐Nor‐1‐thia‐3‐aza‐steroide
  作者：Gerhard Lehmann、Hans Schick、Bernhard Lücke、Günter Hilgetag

  DOI：10.1002/cber.19681010306

  日期：1968.3

  AbstractDie Synthese von A‐Nor‐1‐thia‐3‐aza‐östran‐Derivaten durch Umsetzung von 7‐Oxo‐4.5.6.7‐tetrahydro‐benzothiazolen mit Vinylmagnesiumbromid und anschließende Kondensation mit 2‐Methyl‐cyclopentandion‐(1.3) wird beschrieben.
• 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.