methyl (S)-2-(2-iodo-4-methylphenylamino)-3-methylbutanoate | 865288-83-1

• 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 (S)-2-(2-iodo-4-methylphenylamino)-3-methylbutanoate
• 英文别名: N-(2-iodo-4-methylphenyl)-L-valine methyl ester；methyl (2S)-2-(2-iodo-4-methylanilino)-3-methylbutanoate
• CAS: 865288-83-1
• 化学式: C₁₃H₁₈INO₂
• 分子量: 347.196
• InChiKey: GMHMTVZNNFUXSN-LBPRGKRZSA-N

物化性质

• 沸点：
  365.8±32.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  methyl (S)-2-(2-iodo-4-methylphenylamino)-3-methylbutanoate 在 三乙基硼 、 氧气 、 三正丁基氢锡 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (S)-1-(2-oxo-1-methylindoline)-1-S-isopropyl-acetic acid methyl ester
  参考文献：
  名称：

  Relaying Asymmetry of Transient Atropisomers of o-Iodoanilides by Radical Cyclizations

  摘要：

  Atropisomers of N-2 degrees -alkyl-N-acryloyl-2-iodoanlides have been resolved by chromatography and crystallization-induced asymmetric transformation. These molecules have atropisomerization barriers of 23-24 kcal/mol and return to equilibrium ratios over several hours at ambient temperature in solution. The transient chirality can be locked in by radical cyclizations, which provide N-2 degrees -alkyl-3-methyl-1,3-dihydroindol-2-ones with high levels of chirality transfer. The mechanistic model features a stereoselective aryl radical cyclization that is more rapid than the rotation of the N-aryl bond of the anilide.

  DOI：

  10.1021/ja055666d
• 作为产物：
  描述：

  4-甲苯硼酸 在 copper diacetate 、 4 A molecular sieve 、 N,N,N-trimethylbenzenemethanaminium dichloroiodate 、 calcium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 三乙胺 为溶剂， 反应 14.0h， 生成 methyl (S)-2-(2-iodo-4-methylphenylamino)-3-methylbutanoate
  参考文献：
  名称：

  Relaying Asymmetry of Transient Atropisomers of o-Iodoanilides by Radical Cyclizations

  摘要：

  Atropisomers of N-2 degrees -alkyl-N-acryloyl-2-iodoanlides have been resolved by chromatography and crystallization-induced asymmetric transformation. These molecules have atropisomerization barriers of 23-24 kcal/mol and return to equilibrium ratios over several hours at ambient temperature in solution. The transient chirality can be locked in by radical cyclizations, which provide N-2 degrees -alkyl-3-methyl-1,3-dihydroindol-2-ones with high levels of chirality transfer. The mechanistic model features a stereoselective aryl radical cyclization that is more rapid than the rotation of the N-aryl bond of the anilide.

  DOI：

  10.1021/ja055666d

文献信息

• Synthesis of 1,5-Benzothiazepine Dipeptide Mimetics via Two CuI-Catalyzed Cross Coupling Reactions
  作者：Jiangang Gan、Dawei Ma

  DOI：10.1021/ol900943b

  日期：2009.7.2

  amino acids gives N-aryl amino acids, which are converted into linear dipeptides via iodination and condensation with l-cysteine derived acyl chloride. Cyclization is achieved via a CuI/N,N-dimethylglycine catalyzed intramolecular coupling of aryl iodides with the liberated thiol to afford 1,5-benzothiazepine dipeptide mimetics.

  CuI催化的4-甲基苯基溴化物与氨基酸的偶合生成N-芳基氨基酸，其通过碘化和与1-半胱氨酸衍生的酰氯缩合而转化为线性二肽。通过CuI / N，N，N-二甲基甘氨酸催化的芳基碘化物与释放的硫醇的分子内偶联来实现环化，从而提供1，5-苯并噻氮杂二肽模拟物。