(S)-3-Amino-1-hydroxy-azepan-2-one | 210547-94-7

• 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: (S)-3-Amino-1-hydroxy-azepan-2-one
• 英文别名: (S)-3-Amino-1-hydroxyazepan-2-one；(3S)-3-amino-1-hydroxyazepan-2-one
• CAS: 210547-94-7
• 化学式: C₆H₁₂N₂O₂
• 分子量: 144.173
• InChiKey: GNKNFLLAAAQXII-YFKPBYRVSA-N

物化性质

• 沸点：
  284.0±50.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-Amino-1-hydroxy-azepan-2-one 在 4-二甲氨基吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 [(2R)-4-[[(3S)-1-hydroxy-2-oxoazepan-3-yl]amino]-4-oxobutan-2-yl] (2S)-2-[[2-[[2,3-bis(phenylmethoxy)benzoyl]amino]acetyl]amino]-6-[hexadecanoyl(hydroxy)amino]hexanoate
  参考文献：
  名称：

  含邻苯二酚的霉菌素S和T类似物的合成和研究。

  摘要：

  描述了含邻苯二酚的霉菌素S和T类似物的合成。这些类似物取代了天然分枝杆菌素S和T的苯酚-恶唑啉，取代了儿茶酚-甘氨酸部分。研究表明，新的铁载体类似物结合铁，并促进许多微生物（尤其是分枝杆菌菌株）的生长，例如预期的。

  DOI：

  10.1039/b703116e
• 作为产物：
  描述：

  N-alpha-Cbz-L-赖氨酸 在 palladium on activated charcoal 氢氧化钾 、 N-羟基-7-氮杂苯并三氮唑 、 3 A molecular sieve 、 盐酸羟胺 、 氢气 、 碳酸氢钠 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 68.08h， 生成 (S)-3-Amino-1-hydroxy-azepan-2-one
  参考文献：
  名称：

  含邻苯二酚的霉菌素S和T类似物的合成和研究。

  摘要：

  描述了含邻苯二酚的霉菌素S和T类似物的合成。这些类似物取代了天然分枝杆菌素S和T的苯酚-恶唑啉，取代了儿茶酚-甘氨酸部分。研究表明，新的铁载体类似物结合铁，并促进许多微生物（尤其是分枝杆菌菌株）的生长，例如预期的。

  DOI：

  10.1039/b703116e

文献信息

• Total Synthesis of the Proposed Structure of Mycobactin J
  作者：Chiranjit Ghosh、Sujit Pal、Akanksha Patel、Manmohan Kapur

  DOI：10.1021/acs.orglett.8b02832

  日期：2018.10.19

  The total synthesis of the proposed structure of mycobactin J (MJ), a metabolite of Mycobacterium tuberculosis, is presented. The highlights of the synthesis include a careful control of the Z-stereochemistry of the unsaturated long chain fatty acid, a biomimetic construction of the oxazoline building block and the carriage of an unprotected phenol throughout the synthesis.

  提出了结核分枝杆菌代谢产物分枝杆菌素J（MJ）的拟议结构的全合成。合成的亮点包括仔细控制不饱和长链脂肪酸的Z-立体化学，恶唑啉结构单元的仿生构造以及在整个合成过程中未保护酚的运输。
• β-Lactams in synthesis: short syntheses of cobactin analogs
  作者：Andrew J. Walz、Marvin J. Miller

  DOI：10.1016/j.tetlet.2007.05.085

  日期：2007.7

  Mycobactins facilitate assimilation of iron by mycobacteria. Synthetic analogs with structural variation of the cobactin component have potent anti-TB activity. A new method for the synthesis of cobactin analogs is presented. The key process involves single-step coupling reactions between an amine of a cyclic (l)-lysine derived hydroxamic acid with cyanide activated β-lactams.

  分支杆菌素促进分枝杆菌对铁的吸收。具有烟草素成分结构变化的合成类似物具有有效的抗结核病活性。提出了一种新的合成cobactin类似物的方法。关键过程涉及环状（l）-赖氨酸衍生的异羟肟酸的胺与氰化物活化的β-内酰胺之间的单步偶联反应。
• Synthesis and Biological Activity of Hydroxamic Acid-Derived Vasopeptidase Inhibitor Analogues
  作者：Andrew J. Walz、Marvin J. Miller

  DOI：10.1021/ol025896m

  日期：2002.6.1

  [GRAPHIC]Syntheses of novel hydroxamic acid-derived azepinones containing pendant mercaptoacyl groups or formyl hydroxamates are described. These new analogues of therapeutically important ACE and NEP inhibitors include unprecedented changes at the previously assumed essential acid component.
• Total Syntheses of Mycobactin Analogues as Potent Antimycobacterial Agents Using a Minimal Protecting Group Strategy
  作者：Yanping Xu、Marvin J. Miller

  DOI：10.1021/jo980063o

  日期：1998.6.1

  Mycobactins are a family of iron sequestering agents (siderophores) biosynthesized as growth promoters by mycobacteria including Mycobacterium tuberculosis. They are important siderophores with high affinity and specificity for Fe(III) due to the chemical nature of their component chelating functional groups. The parent compounds and their synthetic analogues can be used for studies of natural iron uptake mechanisms. It was hypothesized by Snow and co-workers that alternate and modified mycobactin analogues might serve as antagonists of mycobacterial growth and be of important therapeutic value. Efficient syntheses of four different analogues are presented. Dramatic improvements on formation of amide and ester bonds were achieved using water soluble carbodiimide (EDC . HCl)-mediated couplings in the presence of 1-hydroxy-7-azabenzotriazole (HOAt) as an additive. Using HOAt over other traditional coupling additives provided significant enhancement of the reaction rate of the desired coupling reactions and minimized side reactions. Further simplifications were made possible by minimizing the use of protecting groups during the syntheses. In fact, coupling components in the presence of free hydroxamic acids and a free phenolic hydroxyl group proceeded in excellent yields. Biological studies indicated that the resulting synthetic analogues effect moderate to high inhibition of the growth of M. tuberculosis H37Rv.