(2S,3R)-5-oxo-2-(((1S,4aS,8as)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)methyl)tetrahydrofuran-3-carboxamide | 1258319-16-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2S,3R)-5-oxo-2-(((1S,4aS,8as)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)methyl)tetrahydrofuran-3-carboxamide
• 英文别名: (2S,3R)-2-[[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-5-oxooxolane-3-carboxamide
• CAS: 1258319-16-2
• 化学式: C₂₀H₃₁NO₃
• 分子量: 333.471
• InChiKey: KUOODSPASQKSFS-TYNWYWJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-4-benzyl-3-((2S,3R)-5-oxo-2-(((1S,4aS,8as)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)methyl)tetrahydrofuran-3-carbonyl)oxazolidin-2-one 在 ammonium acetate 作用下， 反应 0.25h， 生成 (2S,3R)-5-oxo-2-(((1S,4aS,8as)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methyl)tetrahydrofuran-3-carboxamide 、 、 (2S,3R)-5-oxo-2-(((1S,4aS,8as)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)methyl)tetrahydrofuran-3-carboxamide
  参考文献：
  名称：

  A fast and straightforward route towards the synthesis of the lissoclimide class of anti-tumour agents

  摘要：

  The synthesis of the chiral core structure of the lissoclimide class of anti-tumour agents containing three rings including a chiral succinimide subunit and an exocyclic double bond has been investigated The compound 7 was obtained without the use of any protecting groups for the alcohol at C-12 via an asymmetric boron-mediated aldol addition as the key step to install the chiral centres of the rare succimmido methanol moiety This was followed by a sequence of lactonisation microwave-assisted amidation and imidation reactions (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.09.031

文献信息

• A fast and straightforward route towards the synthesis of the lissoclimide class of anti-tumour agents
  作者：Tuan Minh Nguyen、Nguyen Quang Vu、Jean-Jacques Youte、Jacelyn Lau、Angie Cheong、Ying San Ho、Benjamin S.W. Tan、Kanagasundaram Yoganathan、Mark S. Butler、Christina L.L. Chai

  DOI：10.1016/j.tet.2010.09.031

  日期：2010.11

  The synthesis of the chiral core structure of the lissoclimide class of anti-tumour agents containing three rings including a chiral succinimide subunit and an exocyclic double bond has been investigated The compound 7 was obtained without the use of any protecting groups for the alcohol at C-12 via an asymmetric boron-mediated aldol addition as the key step to install the chiral centres of the rare succimmido methanol moiety This was followed by a sequence of lactonisation microwave-assisted amidation and imidation reactions (C) 2010 Elsevier Ltd All rights reserved