(2S,4S,5R,6S)-5-hydroxy-N-methoxy-3-oxo-N,2,4,6-tetramethylnonanamide | 344958-22-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5R,6S)-5-hydroxy-N-methoxy-3-oxo-N,2,4,6-tetramethylnonanamide
• 英文别名: (2S,4S,5R,6S)-5-hydroxy-N-methoxy-N,2,4,6-tetramethyl-3-oxononanamide
• CAS: 344958-22-1
• 化学式: C₁₄H₂₇NO₄
• 分子量: 273.373
• InChiKey: OCINYUYFVWMMMY-FIQHERPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,6S)-5-hydroxy-N-methoxy-3-oxo-N,2,4,6-tetramethylnonanamide 在 zinc(II) tetrahydroborate 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以71%的产率得到(2S,4S,3R,5R,6S)-3,5-dihydroxy-N-methoxy-N,2,4,6-tetramethylnonanamide
  参考文献：
  名称：

  Catalytic, Asymmetric Synthesis of Siphonarienal

  摘要：

  This paper describes the synthesis of the marine natural product, siphonarienal. The key step of this synthesis is an aldol reaction that constructs most of the skeleton and sets all three stereocenters of the target in one step from commercially available starting materials. Deoxygenation and chain homologation steps complete the synthesis.

  DOI：

  10.1021/jo0160367
• 作为产物：
  描述：

  (2S,3R)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide 在 正丁基锂 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.83h， 生成 (2S,4S,5R,6S)-5-hydroxy-N-methoxy-3-oxo-N,2,4,6-tetramethylnonanamide
  参考文献：
  名称：

  Catalytic, Asymmetric Synthesis of Siphonarienal

  摘要：

  This paper describes the synthesis of the marine natural product, siphonarienal. The key step of this synthesis is an aldol reaction that constructs most of the skeleton and sets all three stereocenters of the target in one step from commercially available starting materials. Deoxygenation and chain homologation steps complete the synthesis.

  DOI：

  10.1021/jo0160367

文献信息

• One-Pot, Catalytic, Asymmetric Synthesis of Polypropionates
  作者：Michael A. Calter、Xin Guo、Wensheng Liao

  DOI：10.1021/ol015814e

  日期：2001.5.1

  [reaction: see text] The opening of methylketene dimer, followed by aldol reactions of the resulting enolate, provides a convenient access to syn,syn-dipropionate aldol adducts of a variety of aldehydes. These aldol adducts are useful precursors in the synthesis of complex polypropionates.

  [反应：见正文]甲基烯酮二聚体的打开，随后是生成的烯醇盐的醛醇缩合反应，为各种醛的顺式，正丙酸丙二醇醛醇加合物提供了便利的途径。这些羟醛加合物是合成复杂聚丙烯酸酯的有用前体。
• Catalytic, Asymmetric Synthesis of Siphonarienal
  作者：Michael A. Calter、Wensheng Liao、John A. Struss

  DOI：10.1021/jo0160367

  日期：2001.11.1

  This paper describes the synthesis of the marine natural product, siphonarienal. The key step of this synthesis is an aldol reaction that constructs most of the skeleton and sets all three stereocenters of the target in one step from commercially available starting materials. Deoxygenation and chain homologation steps complete the synthesis.