methyl (1R,2S,5S,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-methylcyclopentanecarboxylate | 1046427-94-4

• 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: methyl (1R,2S,5S,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-methylcyclopentanecarboxylate
• 英文别名: methyl (1R,2S,5S)-2-[benzyl-[(1S)-1-phenylethyl]amino]-5-methylcyclopentane-1-carboxylate
• CAS: 1046427-94-4
• 化学式: C₂₃H₂₉NO₂
• 分子量: 351.489
• InChiKey: OFPKGKVDTPFUGR-YHDSQAASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (1R,2S,5S,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-methylcyclopentanecarboxylate 、 三氟乙酸 在 palladium dihydroxide 氢气 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.25h， 以91%的产率得到methyl (1R,2S,5S)-2-amino-5-methylcyclopentanecarboxylate trifluoroacetic acid salt
  参考文献：
  名称：

  Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate for the asymmetric synthesis of (1R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin

  摘要：

  Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate with a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide provides an efficient entry to the corresponding homochiral methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tris(phenylthio)methyl-cyclopentane-carboxylate derivatives in >98% de, with subsequent, sequential desulfurisation with Raney Nickel, N-debenzylation and ester hydrolysis furnishing (I R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin in high yield, >98% de and >98% ee. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.016
• 作为产物：
  描述：

  methyl (1R,2S,5S,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-tris(phenylthio)methylcyclopentanecarboxylate 在 镍 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以79%的产率得到methyl (1R,2S,5S,αS)-2-[N-benzyl-N-(α-methylbenzyl)amino]-5-methylcyclopentanecarboxylate
  参考文献：
  名称：

  Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate for the asymmetric synthesis of (1R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin

  摘要：

  Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate with a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide provides an efficient entry to the corresponding homochiral methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tris(phenylthio)methyl-cyclopentane-carboxylate derivatives in >98% de, with subsequent, sequential desulfurisation with Raney Nickel, N-debenzylation and ester hydrolysis furnishing (I R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin in high yield, >98% de and >98% ee. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.016

文献信息

• Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate for the asymmetric synthesis of (1R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin
  作者：Elin Abraham、Stephen G. Davies、Alexander J. Docherty、Kenneth B. Ling、Paul M. Roberts、Angela J. Russell、James E. Thomson、Steven M. Toms

  DOI：10.1016/j.tetasy.2008.05.016

  日期：2008.6

  Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate with a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide provides an efficient entry to the corresponding homochiral methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tris(phenylthio)methyl-cyclopentane-carboxylate derivatives in >98% de, with subsequent, sequential desulfurisation with Raney Nickel, N-debenzylation and ester hydrolysis furnishing (I R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin in high yield, >98% de and >98% ee. (C) 2008 Elsevier Ltd. All rights reserved.