Acetic acid (S)-2-acetoxy-1-(5-formyl-2-phenyl-2H-pyrazol-3-yl)-ethyl ester | 1010084-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Acetic acid (S)-2-acetoxy-1-(5-formyl-2-phenyl-2H-pyrazol-3-yl)-ethyl ester
• CAS: 1010084-40-8
• 化学式: C₁₆H₁₆N₂O₅
• 分子量: 316.313
• InChiKey: CLRYOMQSQSCHMU-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  87.49
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (S)-2-acetoxy-1-(5-formyl-2-phenyl-2H-pyrazol-3-yl)-ethyl ester 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成 5-((S)-1,2-Dihydroxy-ethyl)-1-phenyl-1H-pyrazole-3-carbaldehyde
  参考文献：
  名称：

  Hydrophilically functionalized pyrazoles from sugars11Enantiopure Building Blocks from Sugars. Part 22. For Part 21, see Ref.[1].—Presented, in part, at the 9th European Carbohydrate Symposium, Utrecht, The Netherlands, July 1997; Abstract E1.

  摘要：

  An effective and convenient protocol has been developed for the conversion of D-glucose and 6-O-alpha-D-glucopyranosyl-D-fructose (palatinose(R), isomaltulose) into 5-[(1'S)-1',2'-dihydroxyethyl]-1-phenylpyrazole-3-carboxaldehyde (4) and 5-[(1S)-2-(alpha-D-glucopyranosyloxy)-1-hydroxethyl])-1-phenylpyrazole-3-carboxaldehyde (5), key steps being the acetic anhydride-promoted dehydrative cyclization of the respective phenylosazones, and subsequent liberation of the N-acetylphenylhydrazone-blocked aldehyde function. Exploitation of the ensuing chemistry of 4 and 5 led to a variety of pyrazole building blocks with a diverse level of hydrophilic substituents (hydroxymethyl, dihydroxyethyl or glucosyl residues) and useful functional groups, such as chloro, cyano, aminomethyl, vinyl and acryloyl moieties. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00137-2
• 作为产物：
  描述：

  5-(1,2-diacetoxy-ethyl)-1-phenyl-1H-pyrazole-3-carbaldehyde acetyl-phenyl-hydrazone 在 聚合甲醛 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以86%的产率得到Acetic acid (S)-2-acetoxy-1-(5-formyl-2-phenyl-2H-pyrazol-3-yl)-ethyl ester
  参考文献：
  名称：

  Hydrophilically functionalized pyrazoles from sugars11Enantiopure Building Blocks from Sugars. Part 22. For Part 21, see Ref.[1].—Presented, in part, at the 9th European Carbohydrate Symposium, Utrecht, The Netherlands, July 1997; Abstract E1.

  摘要：

  An effective and convenient protocol has been developed for the conversion of D-glucose and 6-O-alpha-D-glucopyranosyl-D-fructose (palatinose(R), isomaltulose) into 5-[(1'S)-1',2'-dihydroxyethyl]-1-phenylpyrazole-3-carboxaldehyde (4) and 5-[(1S)-2-(alpha-D-glucopyranosyloxy)-1-hydroxethyl])-1-phenylpyrazole-3-carboxaldehyde (5), key steps being the acetic anhydride-promoted dehydrative cyclization of the respective phenylosazones, and subsequent liberation of the N-acetylphenylhydrazone-blocked aldehyde function. Exploitation of the ensuing chemistry of 4 and 5 led to a variety of pyrazole building blocks with a diverse level of hydrophilic substituents (hydroxymethyl, dihydroxyethyl or glucosyl residues) and useful functional groups, such as chloro, cyano, aminomethyl, vinyl and acryloyl moieties. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00137-2