ethyl (E)-2-(hydroxyimino)-3-pentenoate | 127032-84-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-2-(hydroxyimino)-3-pentenoate
• 英文别名: ethyl (E)-2-(hydroximino)-3-pentenoate；ethyl (E,2Z)-2-hydroxyiminopent-3-enoate
• CAS: 127032-84-2
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: UZJXUPFCEUTKOP-GMWFMGJWSA-N

物化性质

• 沸点：
  246.6±23.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-(hydroxyimino)-3-pentenoate 在 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 25.0 ℃ 、1300.0 MPa 条件下， 反应 67.5h， 生成 2,2-dimethoxy-6-(ethoxycarbonyl)-3-(methoxycarbonyl)-4-methyl-1-(methylsulfonyl)-1,2,3,4-tetrahydropyridine
  参考文献：
  名称：

  A concise synthesis of the fredericamycin A DEF ring system: [4 + 2] cycloaddition reactions of 1-aza-1,3-butadienes

  摘要：

  A concise four-step synthesis of the fredericamycin A DEF ring system is detailed based on the LUMO(diene)-controlled Diels-Alder reaction of N-sulfonyl-1-azadiene 3 for introduction of the pyridone F ring.

  DOI：

  10.1021/jo00040a044
• 作为产物：
  描述：

  <2-(ethoxycarbonyl)-2-<(2-tetrahydropyranyloxy)imino>ethyl>triphenylphosphonium bromide 在 水 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 64.08h， 生成 ethyl (E)-2-(hydroxyimino)-3-pentenoate
  参考文献：
  名称：

  Boger, Dale L.; Corbett, Wendy L.; Curran, Timothy T., Journal of the American Chemical Society, 1991, vol. 113, # 5, p. 1713 - 1729

  摘要：

  DOI：

文献信息

• Total Synthesis of Natural and ent-Fredericamycin A
  作者：Dale L. Boger、Ottmar Hueter、Kapiamba Mbiya、Minsheng Zhang

  DOI：10.1021/ja00153a004

  日期：1995.12

  A total synthesis of both enantiomers of the potent antitumor-antibiotic fredericamycin A (1) is detailed based on a room temperature inverse electron demand Diels-Alder reaction of a N-sulfonyl-1-aza-1,3-butadiene for assemblage of a pyridone F ring precursor, a single-step Michael addition-intramolecular acylation for annulation of the DE ring system onto this pyridone F ring precursor, implementation of a regiospecific chromium carbene benzannulation reaction for AB ring construction, and a simple aldol closure for introduction of the spiro CD ring system. Resolution of the penultimate precursor 41 followed by deprotection provided natural and ent-fredericamycin A. The indistinguishable cytotoxic potency of the two enantiomers (L1210 IC50, 0.03 and 0.04 mu g/mL, respectively) is disclosed along with that of the key partial structures 2 (IC50 = 2 mu g/mL) and 21 IC50 = 7 mu g/mL) constituting the fully functionalized ABCDE and DEF ring systems of the natural product.
• Room-temperature, endo-specific 1-aza-1,3-butadiene Diels-Alder reactions: acceleration of the LUMOdiene-controlled [4 + 2] cycloaddition reactions through noncomplementary aza diene substitution
  作者：Dale L. Boger、Wendy L. Corbett、J. Mark Wiggins

  DOI：10.1021/jo00297a006

  日期：1990.5
• Boger, Dale L.; Corbett, Wendy L.; Curran, Timothy T., Journal of the American Chemical Society, 1991, vol. 113, # 5, p. 1713 - 1729
  作者：Boger, Dale L.、Corbett, Wendy L.、Curran, Timothy T.、Kasper

  DOI：——

  日期：——
• A concise synthesis of the fredericamycin A DEF ring system: [4 + 2] cycloaddition reactions of 1-aza-1,3-butadienes
  作者：Dale L. Boger、Minsheng Zhang

  DOI：10.1021/jo00040a044

  日期：1992.7

  A concise four-step synthesis of the fredericamycin A DEF ring system is detailed based on the LUMO(diene)-controlled Diels-Alder reaction of N-sulfonyl-1-azadiene 3 for introduction of the pyridone F ring.