3α-methoxy-4α-styryl-2-azetidinone | 132075-34-4

• 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: 3α-methoxy-4α-styryl-2-azetidinone
• 英文别名: (3R,4S)-3-methoxy-4-[(E)-2-phenylethenyl]azetidin-2-one
• CAS: 132075-34-4
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: BTTYFSKJXZRHCB-IAYMVZNDSA-N

物化性质

• 熔点：
  126-127 °C
• 沸点：
  396.1±42.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3α-methoxy-4α-styryl-2-azetidinone 在 吡啶 、 盐酸 、 dirhodium tetraacetate 、 sodium tetrahydroborate 、 硫化氢 、 臭氧 、 甲基磺酰氯 、 三乙胺 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 生成 (6R,7R)-7-Methoxy-3-methyl-4,4,8-trioxo-4λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  对映选择性合成2-isocephem和2-oxa-isocephem抗生素

  摘要：

  描述了在史陶丁格反应中使用-葡糖胺作为手性助剂的旋光2-异欧芬和2-oza-异欧芬核的立体控制合成。

  DOI：

  10.1016/s0040-4039(00)61006-7
• 作为产物：
  描述：

  1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1,3-propanedithio))-D-2'-glucosyl>-3α-methoxy-4α-styryl-2-azetidinone 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 3α-methoxy-4α-styryl-2-azetidinone
  参考文献：
  名称：

  Barton, Derek H. R.; Gateau-Olesker, Alice; Anaya-Mateos, Josefa, Journal of the Chemical Society. Perkin transactions I, 1990, # 11, p. 3211 - 3212

  摘要：

  DOI：

文献信息

• Synthesis and DNA-cleaving activity of lactenediynes conjugated with DNA-complexing moieties
  作者：Luca Banfi、Andrea Basso、Elisabetta Bevilacqua、Valentina Gandolfo、Giuseppe Giannini、Giuseppe Guanti、Loana Musso、Monica Paravidino、Renata Riva

  DOI：10.1016/j.bmc.2008.02.022

  日期：2008.4.1

  Lactenediynes are compounds characterized by the fusion of a beta-lactam with a cyclodeca-3-ene-1,5-diyne. In this work the most promising members of this family have been activated by attaching a carbalkoxy or a carbamoyl group to the azetidinone nitrogen, and conjugated to various DNA-complexing moieties, either acting by intercalation or through groove binding. These conjugated artificial enediynes have been demonstrated to possess in vitro ability to produce single and double strand cleavage of plasmid DNA. As potency and capacity to induce double cut, they rank among the best simple enediyne analogues ever prepared. A thorough investigation was carried out in order to develop the best suited linkers for assembling these conjugates. (C) 2008 Elsevier Ltd. All rights reserved.
• d-Glucosamine propanedithioacetal, an efficient chiral auxiliary in β-Lactam chemistry1Dedicated to Professor Sir Derek H. R. Barton.1
  作者：Josefa Anaya、Stephane D Gero、Manuel Grande、José Ignacio M Hernando、Nieves M Laso

  DOI：10.1016/s0968-0896(98)00264-8

  日期：1999.5

  The synthesis of some monocyclic beta-lactams (monobactams) by the Staudinger reaction using D-glucosamine propanedithioacetal as chiral auxiliary is reported. The influence of several radicals at C-3, C-4, and C-1' (sugar moiety) as well as other structural aspects are considered in relation to the antielastase activity. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Sanchez, Ramon M.; Sanz, Francisca; Grande, Manuel, ARKIVOC, 2010, vol. 2010, # 3, p. 228 - 236
  作者：Sanchez, Ramon M.、Sanz, Francisca、Grande, Manuel、Anayaa, Josefa

  DOI：——

  日期：——
• BARTON, DEREK H. R.;GATEAU-OLESKER, ALICE;ANAYA-MATEOS, JOSEFA;CLEOPHAX, +, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N1, C. 3211-3212
  作者：BARTON, DEREK H. R.、GATEAU-OLESKER, ALICE、ANAYA-MATEOS, JOSEFA、CLEOPHAX, +

  DOI：——

  日期：——
• Barton, Derek H. R.; Gateau-Olesker, Alice; Anaya-Mateos, Josefa, Journal of the Chemical Society. Perkin transactions I, 1990, # 11, p. 3211 - 3212
  作者：Barton, Derek H. R.、Gateau-Olesker, Alice、Anaya-Mateos, Josefa、Cleophax, Jeanine、Gero, Stefan D.、et al.

  DOI：——

  日期：——