ethyl (1R,4S,5R,9S,10R,13S,14R)-14-[[(1R,2R)-2-aminocyclohexyl]carbamothioylamino]-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate | 1352335-16-0

• 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: ethyl (1R,4S,5R,9S,10R,13S,14R)-14-[[(1R,2R)-2-aminocyclohexyl]carbamothioylamino]-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 1352335-16-0
• 化学式: C₂₉H₄₉N₃O₂S
• 分子量: 503.793
• InChiKey: HTGCLINXXHBRKX-QOQWECRWSA-N

物化性质

• 沸点：
  580.5±60.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl ent-16-hydroximinobeyeran-19-oate 在 sodium tetrahydroborate 、 三乙胺 、 molybdenum(VI) oxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 19.33h， 生成 ethyl (1R,4S,5R,9S,10R,13S,14R)-14-[[(1R,2R)-2-aminocyclohexyl]carbamothioylamino]-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
  参考文献：
  名称：

  A highly efficient large-scale asymmetric Michael addition of isobutyraldehyde to maleimides promoted by a novel multifunctional thiourea

  摘要：

  A novel class of chiral multifunctional thioureas bearing a chiral lipophilic beyerane scaffold and a primary amino group were designed and prepared. The thioureas were proven to be effective for catalyzing the asymmetric Michael addition between isobutyraldehyde and maleimides with only 0.5 mol% catalyst loading, and exhibited double asymmetric induction. Both of the catalysts afforded the corresponding adduct with high to excellent yields (up to 98%) and excellent enantioselectivities (up to 99%). Furthermore, this catalytic system can be used efficiently in large-scale reactions with the yields and enantioselectivities being maintained at the same level. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.002
• 作为试剂：
  描述：

  N-苄基马来酰亚胺 、 异丁醛 在 ethyl (1R,4S,5R,9S,10R,13S,14R)-14-[[(1R,2R)-2-aminocyclohexyl]carbamothioylamino]-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate 、 苯甲酸 作用下， 以 氯仿 为溶剂， 以96%的产率得到(R)-2-(1-benzyl-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal
  参考文献：
  名称：

  A highly efficient large-scale asymmetric Michael addition of isobutyraldehyde to maleimides promoted by a novel multifunctional thiourea

  摘要：

  A novel class of chiral multifunctional thioureas bearing a chiral lipophilic beyerane scaffold and a primary amino group were designed and prepared. The thioureas were proven to be effective for catalyzing the asymmetric Michael addition between isobutyraldehyde and maleimides with only 0.5 mol% catalyst loading, and exhibited double asymmetric induction. Both of the catalysts afforded the corresponding adduct with high to excellent yields (up to 98%) and excellent enantioselectivities (up to 99%). Furthermore, this catalytic system can be used efficiently in large-scale reactions with the yields and enantioselectivities being maintained at the same level. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.10.002