(3R,4R)-4-[(2R,5S,6S)-6-[(2S,3S,6R)-6-[(1R,2R)-3-cyano-1-hydroxy-2-methylpropyl]-3-methyloxan-2-yl]-5-methyloxan-2-yl]-4-hydroxy-3-methylbutanenitrile | 140465-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3R,4R)-4-[(2R,5S,6S)-6-[(2S,3S,6R)-6-[(1R,2R)-3-cyano-1-hydroxy-2-methylpropyl]-3-methyloxan-2-yl]-5-methyloxan-2-yl]-4-hydroxy-3-methylbutanenitrile
• CAS: 140465-05-0
• 化学式: C₂₂H₃₆N₂O₄
• 分子量: 392.539
• InChiKey: OMPHUPZLVSAWOH-LAWULNKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  106.5
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3R,4R)-4-[(2R,5S,6S)-6-[(2S,3S,6R)-6-[(1R,2R)-3-cyano-1-hydroxy-2-methylpropyl]-3-methyloxan-2-yl]-5-methyloxan-2-yl]-4-hydroxy-3-methylbutanenitrile 在 盐酸 、 三乙基硅烷 、 氢氧化钾 、 三氟化硼乙醚 、 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 17.17h， 生成 (2S,3S,6R)-3-methyl-2-[(2S,3S,6R)-3-methyl-6-[(2R,3R)-3,4,4-trimethyloxolan-2-yl]oxan-2-yl]-6-[(2R,3R)-3,4,4-trimethyloxolan-2-yl]oxane
  参考文献：
  名称：

  Enantioselective complexation of organic ammonium ions by simple tetracyclic podand ionophores

  摘要：

  A series of enantiomerically pure, C2-symmetric tetracyclic podands are synthesized and studied. These host molecules have methyl substitution, which allows only a few low-energy conformations, and they form well-defined complexes with chiral ammonium salts. With derivatives of alpha-phenethylammonium hexafluorophosphate as guests, binding enantioselectivity ranges from approximately 0 to 60% ee. X-ray structures of several podand/chiral ammonium perchlorate complexes are described along with a conformational analysis of the podands and their complexes.

  DOI：

  10.1021/ja00037a014
• 作为产物：
  描述：

  tert-butyl (4S)-4-[(2S,3S)-3-[(2S)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentan-2-yl]-1,4-dioxaspiro[4.4]nonan-2-yl]pentanoate 在 盐酸 、 叔丁基过氧化氢 、 三甲基氯硅烷 、 bis(acetylacetonate)oxovanadium 、 18-冠醚-6 、 camphor-10-sulfonic acid 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 205.17h， 生成 (3R,4R)-4-[(2R,5S,6S)-6-[(2S,3S,6R)-6-[(1R,2R)-3-cyano-1-hydroxy-2-methylpropyl]-3-methyloxan-2-yl]-5-methyloxan-2-yl]-4-hydroxy-3-methylbutanenitrile
  参考文献：
  名称：

  Enantioselective complexation of organic ammonium ions by simple tetracyclic podand ionophores

  摘要：

  A series of enantiomerically pure, C2-symmetric tetracyclic podands are synthesized and studied. These host molecules have methyl substitution, which allows only a few low-energy conformations, and they form well-defined complexes with chiral ammonium salts. With derivatives of alpha-phenethylammonium hexafluorophosphate as guests, binding enantioselectivity ranges from approximately 0 to 60% ee. X-ray structures of several podand/chiral ammonium perchlorate complexes are described along with a conformational analysis of the podands and their complexes.

  DOI：

  10.1021/ja00037a014