(Z)-(-)-2'-N-benzoylamidocinnamic acid (1S,2R,5S)-menthyl ester | 168974-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-(-)-2'-N-benzoylamidocinnamic acid (1S,2R,5S)-menthyl ester
• 英文别名: [(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl] (Z)-2-benzamido-3-phenylprop-2-enoate
• CAS: 168974-87-6
• 化学式: C₂₆H₃₁NO₃
• 分子量: 405.537
• InChiKey: RCTGJZOWVYZFGM-KYYDNTLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-(-)-2'-N-benzoylamidocinnamic acid (1S,2R,5S)-menthyl ester 在 BF4 、 氢气 作用下， 以 丙酮 为溶剂， 25.0 ℃ 、100.0 kPa 条件下， 生成 (2'S)-(+)-N-benzoyl-phenylalanine (1S,2R,5S)-menthyl ester
  参考文献：
  名称：

  Amplification of double stereodifferentiation in the asymmetric hydrogenation by a solvent effect

  摘要：

  High diastereoselectivities of more than 96 % leading to (S)-amino acid menthyl esters were found in the hydrogenation of both the newly prepared enantiomers 3 and 4 of menthyl (Z)-2-N-benzoylamidocinnamate with the rhodium(I)-chelate of (Ph-beta-glup-OH) 1 as chiral catalyst in polar solvents, The analogous chelate of(Me-alpha-glup) 2 forms a mismached pair with the enantiomer 4 giving the (S)-product in a low diastereoselectivity which can be inversed in the apolar solvent benzene to 86 % of the (R)-diastereomer. Of particular note is the possibility of obtaining high yields either of(R)- or (S)-amino acids with the same catalyst with a single ligand derived from D-glucose.

  DOI：

  10.1016/0957-4166(95)00135-c
• 作为产物：
  描述：

  D-薄荷醇 、 (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one 在 sodium hydride 作用下， 生成 (Z)-(-)-2'-N-benzoylamidocinnamic acid (1S,2R,5S)-menthyl ester
  参考文献：
  名称：

  Amplification of double stereodifferentiation in the asymmetric hydrogenation by a solvent effect

  摘要：

  High diastereoselectivities of more than 96 % leading to (S)-amino acid menthyl esters were found in the hydrogenation of both the newly prepared enantiomers 3 and 4 of menthyl (Z)-2-N-benzoylamidocinnamate with the rhodium(I)-chelate of (Ph-beta-glup-OH) 1 as chiral catalyst in polar solvents, The analogous chelate of(Me-alpha-glup) 2 forms a mismached pair with the enantiomer 4 giving the (S)-product in a low diastereoselectivity which can be inversed in the apolar solvent benzene to 86 % of the (R)-diastereomer. Of particular note is the possibility of obtaining high yields either of(R)- or (S)-amino acids with the same catalyst with a single ligand derived from D-glucose.

  DOI：

  10.1016/0957-4166(95)00135-c

文献信息

• Amplification of double stereodifferentiation in the asymmetric hydrogenation by a solvent effect
  作者：Ulrich Berens、Christine Fischer、Rüdiger Selke

  DOI：10.1016/0957-4166(95)00135-c

  日期：1995.5

  High diastereoselectivities of more than 96 % leading to (S)-amino acid menthyl esters were found in the hydrogenation of both the newly prepared enantiomers 3 and 4 of menthyl (Z)-2-N-benzoylamidocinnamate with the rhodium(I)-chelate of (Ph-beta-glup-OH) 1 as chiral catalyst in polar solvents, The analogous chelate of(Me-alpha-glup) 2 forms a mismached pair with the enantiomer 4 giving the (S)-product in a low diastereoselectivity which can be inversed in the apolar solvent benzene to 86 % of the (R)-diastereomer. Of particular note is the possibility of obtaining high yields either of(R)- or (S)-amino acids with the same catalyst with a single ligand derived from D-glucose.