N-(4-methoxyphenyl)-N'-[trans-(3R,4R)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl]thiourea | 1181819-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: N-(4-methoxyphenyl)-N'-[trans-(3R,4R)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl]thiourea
• 英文别名: 1-(4-methoxyphenyl)-3-[(3R,4R)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl]thiourea
• CAS: 1181819-40-8
• 化学式: C₂₄H₂₃N₃O₃S
• 分子量: 433.531
• InChiKey: CJELUYGPBGANHN-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  94.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N-(4-methoxyphenyl)-N'-[trans-(3R,4R)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl]thiourea 、 甲胺 以 乙醇 、 水 为溶剂， 以13%的产率得到1-(4-methoxyphenyl)-3-[trans-(3'R,4'R)-1'-(4-methoxyphenyl)-2'-oxo-4'-phenylazetidin-3'-yl]-5-methylhexahydro-2-thioxo-1,3,5-triazine
  参考文献：
  名称：

  New Thiazolidinone and Triazinethione Conjugates Derived from Amino-β-lactams

  摘要：

  Thioureas 3a-s, generated from amino-beta-lactams 1a-c, were used to achieve two different cyclizations: (i) condensation with ethyl bromoacetate which resulted in the formation of a variety of iminothiazolidinones 4a/a'-n, and (ii) condensation with aqueous formaldehyde and methylamine which resulted in the formation of triazinethiones 5a-g. The condensation of thioureas 3b-f, 3h and 3m-s (R-1 = cyclohexyl, exo-norbornyl, aryl, R-2 = beta-lactam) with ethyl bromoacetate proceeded with high regioselectivity leading exclusively to the formation of a single regioisomer A of iminothiazolidinones 4b-n. However, the cyclization of thiourea 3a (R-1 = n-hexyl, R-2 = beta-lactam) with ethyl bromoacetate led to the formation of a mixture of two regioisomers A (minor) and B (major) of the iminothiazolidinones 4a/a' in the ratio 23:77. Furthermore, condensation of thioureas 3d, 3g, 3i-1 and 3n with aqueous formaldehyde and methylamine, furnished triazinethiones 5a-g.

  DOI：

  10.3987/com-09-11668
• 作为产物：
  描述：

  trans-(-)-(3R,4R)-3-amino-1-(4-methoxyphenyl)-4-phenylazetidin-2-one 、 4-甲氧基苯基 异硫氰酸酯 以 乙腈 为溶剂， 以99%的产率得到N-(4-methoxyphenyl)-N'-[trans-(3R,4R)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl]thiourea
  参考文献：
  名称：

  New Thiazolidinone and Triazinethione Conjugates Derived from Amino-β-lactams

  摘要：

  Thioureas 3a-s, generated from amino-beta-lactams 1a-c, were used to achieve two different cyclizations: (i) condensation with ethyl bromoacetate which resulted in the formation of a variety of iminothiazolidinones 4a/a'-n, and (ii) condensation with aqueous formaldehyde and methylamine which resulted in the formation of triazinethiones 5a-g. The condensation of thioureas 3b-f, 3h and 3m-s (R-1 = cyclohexyl, exo-norbornyl, aryl, R-2 = beta-lactam) with ethyl bromoacetate proceeded with high regioselectivity leading exclusively to the formation of a single regioisomer A of iminothiazolidinones 4b-n. However, the cyclization of thiourea 3a (R-1 = n-hexyl, R-2 = beta-lactam) with ethyl bromoacetate led to the formation of a mixture of two regioisomers A (minor) and B (major) of the iminothiazolidinones 4a/a' in the ratio 23:77. Furthermore, condensation of thioureas 3d, 3g, 3i-1 and 3n with aqueous formaldehyde and methylamine, furnished triazinethiones 5a-g.

  DOI：

  10.3987/com-09-11668

文献信息

• New Thiazolidinone and Triazinethione Conjugates Derived from Amino-β-lactams
  作者：Ivan Habuš、Katarina Radolović、Bogdan Kralj

  DOI：10.3987/com-09-11668

  日期：——

  Thioureas 3a-s, generated from amino-beta-lactams 1a-c, were used to achieve two different cyclizations: (i) condensation with ethyl bromoacetate which resulted in the formation of a variety of iminothiazolidinones 4a/a'-n, and (ii) condensation with aqueous formaldehyde and methylamine which resulted in the formation of triazinethiones 5a-g. The condensation of thioureas 3b-f, 3h and 3m-s (R-1 = cyclohexyl, exo-norbornyl, aryl, R-2 = beta-lactam) with ethyl bromoacetate proceeded with high regioselectivity leading exclusively to the formation of a single regioisomer A of iminothiazolidinones 4b-n. However, the cyclization of thiourea 3a (R-1 = n-hexyl, R-2 = beta-lactam) with ethyl bromoacetate led to the formation of a mixture of two regioisomers A (minor) and B (major) of the iminothiazolidinones 4a/a' in the ratio 23:77. Furthermore, condensation of thioureas 3d, 3g, 3i-1 and 3n with aqueous formaldehyde and methylamine, furnished triazinethiones 5a-g.