(3S,4S)-3-Amino-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one | 130697-49-3

• 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: (3S,4S)-3-Amino-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one
• 英文别名: (3S,4S)-3-amino-1-(4-methoxyphenyl)-4-phenylazetidin-2-one
• CAS: 130697-49-3
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: XTSXQGSRHGCKDD-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-Amino-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 、 硫代异氰酸苯酯 以 乙腈 为溶剂， 以98%的产率得到N-phenyl-N'-[trans-(3S,4S)-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
• 作为产物：
  描述：

  (2,2,5,5-Tetramethyl-[1,2,5]azadisilolidin-1-yl)-acetic acid 2-phenyl-cyclohexyl ester 、 4-methoxy-N-[(E)-phenylmethylidene]aniline 生成 (3S,4S)-3-Amino-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one
  参考文献：
  名称：

  OJIMA, IWAO;HABUS, IVAN, TETRAHEDRON LETT., 31,(1990) N0, C. 4289-4292

  摘要：

  DOI：

文献信息

• Asymmetric synthesis of β-lactams by chiral ester enolate - imine condensation
  作者：Iwao Ojirna、Ivan I-Iabus

  DOI：10.1016/s0040-4039(00)97603-2

  日期：1990.1

  Asymmetric cyclocondensation of N,N-bis(silyl)glycinates bearing chiral ester moieties with aldimines is found to proceed with extremely high enantioselectivity to give the corresponding chiral β-lactams in good to high yields. It is found that the E/Z-geometry of the chiral ester-enolate ts responsible for cis/trans stereochemistry of the β-lactam formed. Effects of various chiral auxiliaries in the

  发现带有手性酯部分的N，N-双（甲硅烷基）甘氨酸酯与醛亚胺的不对称环缩合以极高的对映选择性进行，从而以良好或高收率得到相应的手性β-内酰胺。发现形成β-内酰胺的顺式/反式立体化学的手性酯-烯醇酸酯ts的E / Z-几何形状。考察了酯-烯酸酯中各种手性助剂对反应对映选择性的影响。
• OJIMA, IWAO;HABUS, IVAN, TETRAHEDRON LETT., 31,(1990) N0, C. 4289-4292
  作者：OJIMA, IWAO、HABUS, IVAN

  DOI：——

  日期：——
• 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.