(+)-tert-butyl 3-methyl-2-propylaminocarbonyloxybutanoate | 1349685-20-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+)-tert-butyl 3-methyl-2-propylaminocarbonyloxybutanoate
• 英文别名: tert-butyl (2S)-3-methyl-2-(propylcarbamoyloxy)butanoate
• CAS: 1349685-20-6
• 化学式: C₁₃H₂₅NO₄
• 分子量: 259.346
• InChiKey: BVMHEEQCYFPAJT-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异氰酸丙酯 、 2-羟基-3-甲基-丁酸-1,1-二甲基乙酸乙酯 在 [Cu((S,S)-((CH3)3CCHCH2OCN)2C(CH3)2)](CF3SO3)2 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 生成 (-)-tert-butyl 3-methyl-2-propylaminocarbonyloxybutanoate 、 (+)-tert-butyl 3-methyl-2-propylaminocarbonyloxybutanoate 、 (R)-2-羟基-3-甲基丁酸叔丁酯 、 (S)-ALPHA羟基异正戊酸叔丁酯
  参考文献：
  名称：

  Kinetic Resolution of Racemic α-tert-Alkyl-α-hydroxy Esters by Enantiomer-Selective Carbamoylation

  摘要：

  Kinetic resolution of sterically hindered racemic alpha-tert-alkyl-alpha-hydroxy esters is performed by enantiomer-selective carbamoylation with the t-Bu-Box-Cu(II) catalyst (Box = bis(oxazoline)). The reaction with 0.5 equiv of n-C3H7NCO is carried out with a substrate-to-catalyst molar ratio of 500-5000 at -20 to 25 degrees C. The high enantiomer-discrimination ability of the catalyst achieves an excellent stereoselectivity factor (s = k(fast)/k(slow)) of 261 in the best case. A catalytic cycle for this reaction is proposed.

  DOI：

  10.1021/jo201940w

文献信息

• Kinetic Resolution of Racemic α-tert-Alkyl-α-hydroxy Esters by Enantiomer-Selective Carbamoylation
  作者：Nobuhito Kurono、Kentaro Ohtsuga、Masanori Wakabayashi、Tadahiro Kondo、Hirohito Ooka、Takeshi Ohkuma

  DOI：10.1021/jo201940w

  日期：2011.12.16

  Kinetic resolution of sterically hindered racemic alpha-tert-alkyl-alpha-hydroxy esters is performed by enantiomer-selective carbamoylation with the t-Bu-Box-Cu(II) catalyst (Box = bis(oxazoline)). The reaction with 0.5 equiv of n-C3H7NCO is carried out with a substrate-to-catalyst molar ratio of 500-5000 at -20 to 25 degrees C. The high enantiomer-discrimination ability of the catalyst achieves an excellent stereoselectivity factor (s = k(fast)/k(slow)) of 261 in the best case. A catalytic cycle for this reaction is proposed.