N-phenyl-N'-[trans-(3R,4R)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl]thiourea | 1181819-32-8

• 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-phenyl-N'-[trans-(3R,4R)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl]thiourea
• 英文别名: 1-[(3R,4R)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl]-3-phenylthiourea
• CAS: 1181819-32-8
• 化学式: C₂₃H₂₁N₃O₂S
• 分子量: 403.505
• InChiKey: SZVAYEBVAJGRJE-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  85.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phenyl-N'-[trans-(3R,4R)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl]thiourea 、 溴乙酸乙酯 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以73%的产率得到2-phenylimino-3-[trans-(3'R,4'R)-1'-(4-methoxyphenyl)-2'-oxo-4'-phenylazetidin-3'-yl]thiazolidin-4-one
  参考文献：
  名称：

  A computational study of regioselectivity in β-lactam iminothiazolidinone formation

  摘要：

  Density functional theory calculations were performed to explain the different regioselectivity for the formation of p-lactam iminothiazolidinones. Computational results were in agreement with experimental observations that phenyl and cyclohexyl derivatives led to the thermodynamically more stable regioisomers formed by cyclization at the nitrogen atom directly attached to the beta-lactam ring which was in contrast to the n-hexyl derivative where the regioisomer with the beta-lactam ring attached to the imino bond is more stable instead. It was demonstrated that the different regioselectivity was the consequence of larger steric effects when bulky substituents and the leaving ethoxy group were in close contact during the cyclization step. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.101
• 作为产物：
  描述：

  trans-(-)-(3R,4R)-3-amino-1-(4-methoxyphenyl)-4-phenylazetidin-2-one 、 硫代异氰酸苯酯 以 乙腈 为溶剂， 反应 24.0h， 以96%的产率得到N-phenyl-N'-[trans-(3R,4R)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl]thiourea
  参考文献：
  名称：

  A computational study of regioselectivity in β-lactam iminothiazolidinone formation

  摘要：

  Density functional theory calculations were performed to explain the different regioselectivity for the formation of p-lactam iminothiazolidinones. Computational results were in agreement with experimental observations that phenyl and cyclohexyl derivatives led to the thermodynamically more stable regioisomers formed by cyclization at the nitrogen atom directly attached to the beta-lactam ring which was in contrast to the n-hexyl derivative where the regioisomer with the beta-lactam ring attached to the imino bond is more stable instead. It was demonstrated that the different regioselectivity was the consequence of larger steric effects when bulky substituents and the leaving ethoxy group were in close contact during the cyclization step. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.101

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.
• A computational study of regioselectivity in β-lactam iminothiazolidinone formation
  作者：Katarina Vazdar、Mario Vazdar

  DOI：10.1016/j.tetlet.2015.10.101

  日期：2015.12

  Density functional theory calculations were performed to explain the different regioselectivity for the formation of p-lactam iminothiazolidinones. Computational results were in agreement with experimental observations that phenyl and cyclohexyl derivatives led to the thermodynamically more stable regioisomers formed by cyclization at the nitrogen atom directly attached to the beta-lactam ring which was in contrast to the n-hexyl derivative where the regioisomer with the beta-lactam ring attached to the imino bond is more stable instead. It was demonstrated that the different regioselectivity was the consequence of larger steric effects when bulky substituents and the leaving ethoxy group were in close contact during the cyclization step. (C) 2015 Elsevier Ltd. All rights reserved.