methyl N-[(1,1-dimethylethoxy)carbonyl]-O-(5-chloro-6-oxo-1-cyclohexenyl)tyrosinate | 193410-62-7

• 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: methyl N-[(1,1-dimethylethoxy)carbonyl]-O-(5-chloro-6-oxo-1-cyclohexenyl)tyrosinate
• 英文别名: methyl (2S)-3-[4-(5-chloro-6-oxocyclohexen-1-yl)oxyphenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 193410-62-7
• 化学式: C₂₁H₂₆ClNO₆
• 分子量: 423.894
• InChiKey: SYJOZNMNDDGKTL-LYKKTTPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl N-[(1,1-dimethylethoxy)carbonyl]-O-(5-chloro-6-oxo-1-cyclohexenyl)tyrosinate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 chloroamine-T 、 四丁基碘化铵 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三(邻甲基苯基)磷 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 39.5h， 生成 methyl N-[(1,1-dimethylethoxy)carbonyl]-O-[S]-[5-({[2-(1,1-dimethylethoxy)carbonyl]amino}-2-[(phenylmethoxy)carbonyl]ethyl)-2-(phenylmethoxy)phenyl]-L-tyrosinate
  参考文献：
  名称：

  Total Synthesis of (S,S)-Isodityrosine[]

  摘要：

  The novel dimeric amino acid isodityrosine 1 has been synthesized by a route which uses a new method of diaryl ether preparation. Nucleophilic addition of a protected tyrosine to cyclohexenone oxide and the Pd(O)-catalyzed coupling of an aryl iodide with a protected iodoalanine derivative are the key steps in this synthesis. This represents one of the first efficient syntheses of this molecule beginning with two naturally-occurring amino acids as inexpensive starting materials (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00570-x
• 作为产物：
  描述：

  7-氧杂二环[4.1.0]庚烷-2-酮 在 sodium hydroxide 、 苯基氯化硒 、 苄基三乙基氯化铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 63.0h， 生成 methyl N-[(1,1-dimethylethoxy)carbonyl]-O-(5-chloro-6-oxo-1-cyclohexenyl)tyrosinate
  参考文献：
  名称：

  Total Synthesis of (S,S)-Isodityrosine[]

  摘要：

  The novel dimeric amino acid isodityrosine 1 has been synthesized by a route which uses a new method of diaryl ether preparation. Nucleophilic addition of a protected tyrosine to cyclohexenone oxide and the Pd(O)-catalyzed coupling of an aryl iodide with a protected iodoalanine derivative are the key steps in this synthesis. This represents one of the first efficient syntheses of this molecule beginning with two naturally-occurring amino acids as inexpensive starting materials (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00570-x

文献信息

• Total Synthesis of (S,S)-Isodityrosine[]
  作者：M Jung*[]

  DOI：10.1016/s0040-4020(97)00570-x

  日期：1997.6.30

  The novel dimeric amino acid isodityrosine 1 has been synthesized by a route which uses a new method of diaryl ether preparation. Nucleophilic addition of a protected tyrosine to cyclohexenone oxide and the Pd(O)-catalyzed coupling of an aryl iodide with a protected iodoalanine derivative are the key steps in this synthesis. This represents one of the first efficient syntheses of this molecule beginning with two naturally-occurring amino acids as inexpensive starting materials (C) 1997 Elsevier Science Ltd.