O⁴-Benzyl-N-(tert-butyloxycarbonyl)neoenactin A | 154617-89-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O⁴-Benzyl-N-(tert-butyloxycarbonyl)neoenactin A
• 英文别名: tert-butyl N-[(2S)-1-[3,10-dioxohexadecyl(phenylmethoxy)amino]-3-hydroxy-1-oxopropan-2-yl]carbamate
• CAS: 154617-89-7
• 化学式: C₃₁H₅₀N₂O₇
• 分子量: 562.747
• InChiKey: XCZMCLFHWAXRDM-NDEPHWFRSA-N

物化性质

• 密度：
  1.088±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  40
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  O⁴-Benzyl-N-(tert-butyloxycarbonyl)neoenactin A 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 Neoenactin A
  参考文献：
  名称：

  Synthesis of the Antifungal Agent Neoenactin A and Its N-Deshydroxy Derivative

  摘要：

  The first total and unequivocal syntheses of neoenactin A (1, NE A) as well as its N-deshydroxy analog 2 are described. The two key steps in the syntheses were the oxidative cleavage of an appropriate olefin 8a to yield the desired keto acid 9 and the Michael addition of serinehydroxamates 11 or 12 to the appropriate vinyl ketone 10. Biological activity of 1 and 2 against Escherichia coli and several fungi has been investigated.

  DOI：

  10.1021/jo00081a027
• 作为产物：
  描述：

  8-氧代十四烷酸 在 benzoylchlorobis(triphenylphosphine)palladium(II) 草酰氯 、 potassium tert-butylate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 苯 为溶剂， 反应 169.5h， 生成 O⁴-Benzyl-N-(tert-butyloxycarbonyl)neoenactin A
  参考文献：
  名称：

  Synthesis of the Antifungal Agent Neoenactin A and Its N-Deshydroxy Derivative

  摘要：

  The first total and unequivocal syntheses of neoenactin A (1, NE A) as well as its N-deshydroxy analog 2 are described. The two key steps in the syntheses were the oxidative cleavage of an appropriate olefin 8a to yield the desired keto acid 9 and the Michael addition of serinehydroxamates 11 or 12 to the appropriate vinyl ketone 10. Biological activity of 1 and 2 against Escherichia coli and several fungi has been investigated.

  DOI：

  10.1021/jo00081a027

文献信息

• Synthesis of the Antifungal Agent Neoenactin A and Its N-Deshydroxy Derivative
  作者：Ihab S. Darwish、Marvin J. Miller

  DOI：10.1021/jo00081a027

  日期：1994.1

  The first total and unequivocal syntheses of neoenactin A (1, NE A) as well as its N-deshydroxy analog 2 are described. The two key steps in the syntheses were the oxidative cleavage of an appropriate olefin 8a to yield the desired keto acid 9 and the Michael addition of serinehydroxamates 11 or 12 to the appropriate vinyl ketone 10. Biological activity of 1 and 2 against Escherichia coli and several fungi has been investigated.