dimethyl <(4,5,6,7-tetrahydro-7-hydroxy-2-phenyl)benzothiazol-7-yl>phosphonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: dimethyl <(4,5,6,7-tetrahydro-7-hydroxy-2-phenyl)benzothiazol-7-yl>phosphonate
• 英文别名: 7-dimethoxyphosphoryl-2-phenyl-5,6-dihydro-4H-1,3-benzothiazol-7-ol
• 化学式: C₁₅H₁₈NO₄PS
• 分子量: 339.352
• InChiKey: RIGOACQEKVJBPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  96.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  硫代苯甲酰胺 、 dimethyl (1,2-epoxy-3-oxo-cyclohex-1-yl)phosphonate 以 乙醇 为溶剂， 反应 9.0h， 以88%的产率得到dimethyl <(4,5,6,7-tetrahydro-7-hydroxy-2-phenyl)benzothiazol-7-yl>phosphonate
  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

• 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.