benzyl (1S,2R)-2-{[(1'R)-1'-phenylethyl]amino}cyclohexanecarboxylate | 383905-40-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl (1S,2R)-2-{[(1'R)-1'-phenylethyl]amino}cyclohexanecarboxylate
• 英文别名: benzyl (1S,2R)-2-[[(1R)-1-phenylethyl]amino]cyclohexane-1-carboxylate
• CAS: 383905-40-6
• 化学式: C₂₂H₂₇NO₂
• 分子量: 337.462
• InChiKey: ZSWYBHUFWDBALE-JRGCBEDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl (1S,2R)-2-{[(1'R)-1'-phenylethyl]amino}cyclohexanecarboxylate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以84%的产率得到(1RS,2SR)-2-aminocyclohexanecarboxylic acid
  参考文献：
  名称：

  AN IMPROVED SYNTHESIS OF ENANTIOPURE β-AMINO ACIDS

  摘要：

  An improved method for the preparation of both the enantiopure beta -amino acids is presented. The diastereomer benzyl beta -amino esters, obtained by stereoselective reduction of beta -enamino esters, were separated and hydrogenolyzed to the free enantiopure beta -amino acids.

  DOI：

  10.1081/scc-100105666
• 作为产物：
  描述：

  benzyl 2-[[(1R)-1-phenylethyl]amino]cyclohexene-1-carboxylate 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以74%的产率得到benzyl (1S,2R)-2-{[(1'R)-1'-phenylethyl]amino}cyclohexanecarboxylate
  参考文献：
  名称：

  AN IMPROVED SYNTHESIS OF ENANTIOPURE β-AMINO ACIDS

  摘要：

  An improved method for the preparation of both the enantiopure beta -amino acids is presented. The diastereomer benzyl beta -amino esters, obtained by stereoselective reduction of beta -enamino esters, were separated and hydrogenolyzed to the free enantiopure beta -amino acids.

  DOI：

  10.1081/scc-100105666

文献信息

• A practical synthesis of enantiopure N-carbobenzyloxy-N′-phthaloyl-cis-1,2-cyclohexanediamine by asymmetric reductive amination and the Curtius rearrangement
  作者：Jun-ichi Matsuo、Masahiko Okano、Kosuke Takeuchi、Hiroyuki Tanaka、Hiroyuki Ishibashi

  DOI：10.1016/j.tetasy.2007.08.014

  日期：2007.8

  Enantionterically pure N-carbobenzyloxy-N'-phthaloyl-cis-1,2-cyclohexanediamine was synthesized by the asymmetric reduction of a beta-enamino ester formed from benzyl 2-oxocycloliexanecarboxylate and (R)-phenylethylamine, followed by hydrogenolysis, phthaloylation, and the Curtius rearrangement. (c) 2007 Elsevier Ltd. All rights reserved.
• AN IMPROVED SYNTHESIS OF ENANTIOPURE β-AMINO ACIDS
  作者：Cristina Cimarelli、Gianni Palmieri、Emanuela Volpini

  DOI：10.1081/scc-100105666

  日期：2001.1

  An improved method for the preparation of both the enantiopure beta -amino acids is presented. The diastereomer benzyl beta -amino esters, obtained by stereoselective reduction of beta -enamino esters, were separated and hydrogenolyzed to the free enantiopure beta -amino acids.