(2R,5S)-2-dodecanoyl-3-phenyl-1,3-diazabicyclo[3.3.0]-octane | 959781-09-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (2R,5S)-2-dodecanoyl-3-phenyl-1,3-diazabicyclo[3.3.0]-octane
• 英文别名: 1-[(3R,7aS)-2-phenyl-1,3,5,6,7,7a-hexahydropyrrolo[1,2-c]imidazol-3-yl]dodecan-1-one
• CAS: 959781-09-0
• 化学式: C₂₄H₃₈N₂O
• 分子量: 370.579
• InChiKey: QBYNHHVDZMDXTM-LADGPHEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,5S)-2-dodecanoyl-3-phenyl-1,3-diazabicyclo[3.3.0]-octane 在 咪唑 、 盐酸 、 sodium tetrahydroborate 、 碘 、 magnesium 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.25h， 生成 methyl (R)-5-tert-butyldiphenylsiloxymethyl-5-hydroxymethylhexadecanoate
  参考文献：
  名称：

  Concise asymmetric synthesis of (R)-(+)-tanikolide

  摘要：

  A highly stereoselective total synthesis of (R)-(+)-tanikolide, a delta-lactonic marine natural product, was accomplished in seven steps from easily available starting materials with a 51% overall yield. An asymmetric synthesis of an alpha-hydroxy aldehyde having a stereogenic quaternary center, by the use of (S)-2-(anilinomethyl) pyrrolidine as a chiral auxiliary, was employed in a key step. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.09.012
• 作为产物：
  描述：

  (S)-(+)-2-(苯胺甲基)吡咯烷 在 碘 、 magnesium 作用下， 以 乙醚 、 苯 为溶剂， 反应 1.33h， 生成 (2R,5S)-2-dodecanoyl-3-phenyl-1,3-diazabicyclo[3.3.0]-octane
  参考文献：
  名称：

  Concise asymmetric synthesis of (R)-(+)-tanikolide

  摘要：

  A highly stereoselective total synthesis of (R)-(+)-tanikolide, a delta-lactonic marine natural product, was accomplished in seven steps from easily available starting materials with a 51% overall yield. An asymmetric synthesis of an alpha-hydroxy aldehyde having a stereogenic quaternary center, by the use of (S)-2-(anilinomethyl) pyrrolidine as a chiral auxiliary, was employed in a key step. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.09.012

文献信息

• Concise asymmetric synthesis of (R)-(+)-tanikolide
  作者：Chenxia Zhang、Naoya Hosoda、Masatoshi Asami

  DOI：10.1016/j.tetasy.2007.09.012

  日期：2007.9

  A highly stereoselective total synthesis of (R)-(+)-tanikolide, a delta-lactonic marine natural product, was accomplished in seven steps from easily available starting materials with a 51% overall yield. An asymmetric synthesis of an alpha-hydroxy aldehyde having a stereogenic quaternary center, by the use of (S)-2-(anilinomethyl) pyrrolidine as a chiral auxiliary, was employed in a key step. (c) 2007 Elsevier Ltd. All rights reserved.