(2S,5R,6R)-6-((E)-3-{2-[((2E,4E)-Hexa-2,4-dienyl)oxy]-3-methoxy-phenyl}-acryloylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester | 847591-26-8

• 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: (2S,5R,6R)-6-((E)-3-{2-[((2E,4E)-Hexa-2,4-dienyl)oxy]-3-methoxy-phenyl}-acryloylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,5R,6R)-6-[[(E)-3-[2-[(2E,4E)-hexa-2,4-dienoxy]-3-methoxyphenyl]prop-2-enoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 847591-26-8
• 化学式: C₂₅H₃₀N₂O₆S
• 分子量: 486.589
• InChiKey: WDHSNNYIEAOGHF-GOTMWKSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,5R,6R)-6-((E)-3-{2-[((2E,4E)-Hexa-2,4-dienyl)oxy]-3-methoxy-phenyl}-acryloylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester 以 乙腈 为溶剂， 反应 72.0h， 以70%的产率得到(2S,5R,6R)-6-{(E)-3-[2-Hydroxy-3-methoxy-5-((E)-1-methyl-penta-2,4-dienyl)-phenyl]-acryloylamino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Domino functionalizations of the amino terminus of 6-aminopenicillanates with Ph3PCCO

  摘要：

  6-Aminopenicillanates, or the sulfoxides or the sulfones thereof, were N-acylated in a three-component reaction with an aldehyde and Ph3PCCO to give the corresponding 6-(E-2'-alkenoyl)amides. This domino addition-Wittig alkenation sequence was extended by an additional Claisen rearrangement step in the side-chain in the case of 5g. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.083
• 作为产物：
  描述：

  sorbyl bromide 在 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (2S,5R,6R)-6-((E)-3-{2-[((2E,4E)-Hexa-2,4-dienyl)oxy]-3-methoxy-phenyl}-acryloylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Domino functionalizations of the amino terminus of 6-aminopenicillanates with Ph3PCCO

  摘要：

  6-Aminopenicillanates, or the sulfoxides or the sulfones thereof, were N-acylated in a three-component reaction with an aldehyde and Ph3PCCO to give the corresponding 6-(E-2'-alkenoyl)amides. This domino addition-Wittig alkenation sequence was extended by an additional Claisen rearrangement step in the side-chain in the case of 5g. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.083