O-menthyl-(R)-phenylalanine

• 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: O-menthyl-(R)-phenylalanine
• 英文别名: D-Phe-menthylester；D-Phenylalanin-menthylester；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (2R)-2-amino-3-phenylpropanoate
• 化学式: C₁₉H₂₉NO₂
• 分子量: 303.445
• InChiKey: ZLLWKHXVYCYMAF-BZZMCLGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 O-menthyl-(R)-phenylalanine 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以0.057 g的产率得到(R)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) 2-(((9Hfluoren-9-yl)methoxy)carbonyl)amino-3-phenylpropanoate
  参考文献：
  名称：

  Convenient Synthetic Route to an Enantiomerically Pure FMOC α-Amino Acid

  摘要：

  A strategy for the facile alpha-amination of carboxylic acid menthyl esters is described. The resulting diastereomers, readily separable, can be individually carried on to each enantiomer of the FMOC alpha-amino acid. A variety of unnatural side chains were compatible with this approach. The menthyl ester was easily removed from the FMOC alpha-amino acid without racermization.

  DOI：

  10.1021/jo801781v
• 作为产物：
  描述：

  (R)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) 2-(2-methoxyphenylamino)-3-phenylpropanoate 在 碘苯二乙酸 、 溶剂黄146 、 盐酸 、 水 、 sodium carbonate 、 sodium thiosulfate 作用下， 以 甲醇 为溶剂， 反应 1.17h， 生成 O-menthyl-(R)-phenylalanine
  参考文献：
  名称：

  Convenient Synthetic Route to an Enantiomerically Pure FMOC α-Amino Acid

  摘要：

  A strategy for the facile alpha-amination of carboxylic acid menthyl esters is described. The resulting diastereomers, readily separable, can be individually carried on to each enantiomer of the FMOC alpha-amino acid. A variety of unnatural side chains were compatible with this approach. The menthyl ester was easily removed from the FMOC alpha-amino acid without racermization.

  DOI：

  10.1021/jo801781v

文献信息

• The Synthesis of α-Amino Acid Menthyl Esters. II
  作者：Tadao Hayakawa、Kaoru Harada

  DOI：10.1246/bcsj.38.1354

  日期：1965.8

  Synthesis of alpha-amino acid l-menthyl esters under mild conditions, using alpha-amino acid N- carboxy anhydride /NCA/ and l-menthol

  使用α-氨基酸N-羧酸酐/NCA/和l-薄荷醇在温和条件下合成α-氨基酸l-薄荷酯
• Davenport, Kenneth G.; Mao, David T.; Richmond, Cliff M., Journal of Chemical Research, Miniprint, 1984, # 5, p. 1518 - 1530
  作者：Davenport, Kenneth G.、Mao, David T.、Richmond, Cliff M.、Bergbreiter, David E.、Newcomb, Martin

  DOI：——

  日期：——
• Syntheses of α-Amino Acid Menthyl Esters
  作者：Kaoru Harada、Tadao Hayakawa

  DOI：10.1246/bcsj.37.191

  日期：1964.2
• Convenient Synthetic Route to an Enantiomerically Pure FMOC α-Amino Acid
  作者：Douglass F. Taber、James F. Berry、Timothy J. Martin

  DOI：10.1021/jo801781v

  日期：2008.12.5

  A strategy for the facile alpha-amination of carboxylic acid menthyl esters is described. The resulting diastereomers, readily separable, can be individually carried on to each enantiomer of the FMOC alpha-amino acid. A variety of unnatural side chains were compatible with this approach. The menthyl ester was easily removed from the FMOC alpha-amino acid without racermization.