(E)-3-ethylidene-4-phenyl-1-(1,3-thiazol-2-yl)-azetidin-2-one | 918891-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: (E)-3-ethylidene-4-phenyl-1-(1,3-thiazol-2-yl)-azetidin-2-one
• 英文别名: (3E)-3-ethylidene-4-phenyl-1-(1,3-thiazol-2-yl)azetidin-2-one
• CAS: 918891-41-5
• 化学式: C₁₄H₁₂N₂OS
• 分子量: 256.328
• InChiKey: OTANVBLKFQRONX-BIIKFXOESA-N

物化性质

• 熔点：
  158-159 °C(Solv: ligroine (8032-32-4))
• 沸点：
  409.0±55.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-ethylidene-4-phenyl-1-(1,3-thiazol-2-yl)-azetidin-2-one 、 sodium methylate 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到methyl 2-[phenyl(thiazol-2-ylamino)methyl]-2-butenoate
  参考文献：
  名称：

  内酰胺核和迈克尔反应的串联选择性键裂解

  摘要：

  已经研究了 β-内酰胺环对亲核试剂的反应性。在室温和/或回流下，用 CH3O-/CH3OH 对 3-烯丙基-β-内酰胺进行开环反应。内酰胺核异构化，然后 N1-C2 键断裂和甲醇迈克尔加成得到取代的氨基酯。发现四元环对亲核试剂的反应性取决于内酰胺氮以及 C3 和 C4 原子上的取代基。本报告突出显示了开环路径。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200600597
• 作为产物：
  描述：

  一氧化碳 、 benzylidene-1,3-thiazol-2-yl-amine 、 3-溴丙烯 在 palladium diacetate 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 100.0 ℃ 、2.76 MPa 条件下， 以43%的产率得到(E)-3-ethylidene-4-phenyl-1-(1,3-thiazol-2-yl)-azetidin-2-one
  参考文献：
  名称：

  Synthesis and isomerization of N-α-aza-heteroaryl-β-lactams

  摘要：

  The [2+2] carbonylative cycloaddition of N-cx-aza-heteroaryl substituted imines with allyl bromide led partially to beta-lactams, which underwent isomerization to the more stable alpha,beta-unsaturated carbonyl compound. Pyrimidinone derivatives together with doubly unsaturated amides represent the remaining isolated products. The strong electron-withdrawing effect of the two alpha-aza-heterocycles linked to the nitrogen atom and to the C4 of the 2-azetidinone structure could give a ring expansion, through a 2-azetinone intermediate that affords the pyrimidinone compounds. The substituted amides, instead, should result from a ring-opening reaction of the beta-lactam. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.075

文献信息

• Synthesis and isomerization of N-α-aza-heteroaryl-β-lactams
  作者：Luigino Troisi、Ludovico Ronzini、Catia Granito、Emanuela Pindinelli、Alessandro Troisi、Tullio Pilati

  DOI：10.1016/j.tet.2006.09.075

  日期：2006.12

  The [2+2] carbonylative cycloaddition of N-cx-aza-heteroaryl substituted imines with allyl bromide led partially to beta-lactams, which underwent isomerization to the more stable alpha,beta-unsaturated carbonyl compound. Pyrimidinone derivatives together with doubly unsaturated amides represent the remaining isolated products. The strong electron-withdrawing effect of the two alpha-aza-heterocycles linked to the nitrogen atom and to the C4 of the 2-azetidinone structure could give a ring expansion, through a 2-azetinone intermediate that affords the pyrimidinone compounds. The substituted amides, instead, should result from a ring-opening reaction of the beta-lactam. (c) 2006 Elsevier Ltd. All rights reserved.
• Tandem-Selective Bond Cleavage of the Lactam Nucleus and Michael Reaction
  作者：Luisella De Vitis、Luigino Troisi、Catia Granito、Emanuela Pindinelli、Ludovico Ronzini

  DOI：10.1002/ejoc.200600597

  日期：2007.1

  The reactivity of the β-lactam ring towards nucleophiles has been investigated. Ring-opening reactions were performed on 3-allyl-β-lactams with CH3O–/CH3OH at room temperature and/or reflux. Lactam nucleus isomerization followed by N1–C2 bond cleavage and methanol Michael addition afforded substituted amino esters. The reactivity of the four-membered ring towards nucleophiles was found to depend on

  已经研究了 β-内酰胺环对亲核试剂的反应性。在室温和/或回流下，用 CH3O-/CH3OH 对 3-烯丙基-β-内酰胺进行开环反应。内酰胺核异构化，然后 N1-C2 键断裂和甲醇迈克尔加成得到取代的氨基酯。发现四元环对亲核试剂的反应性取决于内酰胺氮以及 C3 和 C4 原子上的取代基。本报告突出显示了开环路径。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)