cis-3-methoxy-4-(prop-1-enyl)azetidin-2-one | 101535-99-3

• 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: cis-3-methoxy-4-(prop-1-enyl)azetidin-2-one
• 英文别名: (3R,4S)-3-methoxy-4-[(E)-prop-1-enyl]azetidin-2-one
• CAS: 101535-99-3
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: KVVCOYXJOBXLKE-NBZFHMRBSA-N

物化性质

• 沸点：
  273.8±40.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  cis-3-methoxy-4-(prop-1-enyl)azetidin-2-one 在 氢氧化钾 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 (E)-(2R,3S)-3-Benzoylamino-2-methoxy-hex-4-enoic acid
  参考文献：
  名称：

  Manhas, Maghar S.; Hedge, Vinod R.; Wagle, Dilip R., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2045 - 2050

  摘要：

  DOI：
• 作为产物：
  描述：

  cis-3-methoxy-1-(4-methoxyphenyl)-4-(prop-1-enyl)azetidin-2-one 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以83%的产率得到cis-3-methoxy-4-(prop-1-enyl)azetidin-2-one
  参考文献：
  名称：

  Manhas, Maghar S.; Hedge, Vinod R.; Wagle, Dilip R., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2045 - 2050

  摘要：

  DOI：

文献信息

• Studies on Nonconventionally Fused Bicyclic β-Lactams
  作者：Xiao-Feng Ren、Monika I. Konaklieva、Hongchang Shi、Sonja Dickey、Daniel V. Lim、Javier Gonzalez、Edward Turos

  DOI：10.1021/jo9811219

  日期：1998.11.1

  Described in this article are studies of structurally novel [3.2.0]bicyclic beta-lactam ring systems that are isomeric to those of the penicillin, penem, and clavulanic acid families of antibiotics, but which have the lactam functionality arranged in alternative orientations within the four-membered ring. Semiempirical calculations indicate that the thermodynamic stabilities of the three alternative isomeric ring systems are similar to that of the classical penam or penem structure, and ab initio methods reveal that the LUMO energies of the two C-fused ring structures 11 and 12 are more than 1 eV lower than that of 2-azetidinone, but 0.22 to 0.73 eV higher than that of the penem ring 13. The LUMO energy of the N-S fused penem structure 14 is about 0.2 eV lower than that of 13. These studies also suggest that the N-fused bicyclic beta-lactams are considerably more electrophilic than the corresponding C-fused compounds. Several of the new heterocyclic rings were synthesized using a two-step cyclization strategy to assemble the bicyclic core. First, the beta-lactam ring was created by a Staudinger reaction of an acid chloride and alpha,beta-unsaturated imine, and the sulfur heterocycle was closed through a halogen-promoted cyclization reaction of a sulfur substituent onto a neighboring alkenyl or alkynyl side chain. Using palladium catalysis, iodopenem adducts 18, 31a, and 56a were converted to vinyl- and heteroaryl-substituted derivatives, carboxylic esters, and carboxylic acids. Four of the bicyclic beta-lactams prepared in this study (58b, 80, 87, and 89) showed weak levels of activity against Staphylococcus aureus or Vibrio cholerae.
• Manhas, Maghar S.; Hedge, Vinod R.; Wagle, Dilip R., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2045 - 2050
  作者：Manhas, Maghar S.、Hedge, Vinod R.、Wagle, Dilip R.、Bose, Ajay K.

  DOI：——

  日期：——