ethyl (1R,4S,5R,9S,10R,13S,14R)-14-[[(1S,2S)-2-aminocyclohexyl]carbamothioylamino]-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate | 1352335-13-7

• 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-[[(1S,2S)-2-aminocyclohexyl]carbamothioylamino]-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 1352335-13-7
• 化学式: C₂₉H₄₉N₃O₂S
• 分子量: 503.793
• InChiKey: HTGCLINXXHBRKX-NDTITTEISA-N

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-16β-aminobeyeran-19-oate 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 13.33h， 生成 ethyl (1R,4S,5R,9S,10R,13S,14R)-14-[[(1S,2S)-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-(4-硝基苯基)马来酰亚胺 、 异丁醛 在 ethyl (1R,4S,5R,9S,10R,13S,14R)-14-[[(1S,2S)-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75%的产率得到(S)-2-methyl-2-(1-(4-nitrophenyl)-2,5-dioxopyrrolidin-3-yl)propanal
  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

文献信息

• A highly efficient large-scale asymmetric Michael addition of isobutyraldehyde to maleimides promoted by a novel multifunctional thiourea
  作者：Zhi-wei Ma、Yu-xia Liu、Pan-li Li、Hang Ren、Yu Zhu、Jing-chao Tao

  DOI：10.1016/j.tetasy.2011.10.002

  日期：2011.10

  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.