tert-butyl (3-(((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)(methyl)amino)-3-oxopropyl)carbamate | 1354086-68-2

• 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: tert-butyl (3-(((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)(methyl)amino)-3-oxopropyl)carbamate
• CAS: 1354086-68-2
• 化学式: C₁₈H₂₈N₂O₄
• 分子量: 336.431
• InChiKey: DHSCSMKGGLVRIE-BBRMVZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.87
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (3-(((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)(methyl)amino)-3-oxopropyl)carbamate 在 盐酸 、 1H-咪唑-1-磺酰叠氮盐酸盐 、 sodium hydride 、 potassium carbonate 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 甲苯 、 mineral oil 为溶剂， 生成 3-azido-N-methyl-N-[(1R,2S)-1-phenyl-1-prop-2-ynoxypropan-2-yl]propanamide
  参考文献：
  名称：

  Strained Cyclophane Macrocycles: Impact of Progressive Ring Size Reduction on Synthesis and Structure

  摘要：

  The synthesis, X-ray, crystal structures, and calculated strain energies are reported for a homologous series of 11- to 14-membered drug-like cyclophane macrocycles, representing an unusual region of chemical space that can be difficult to access synthetically. The ratio of macrocycle to dimer, generated via a copper catalyzed azide-alkyne cycloaddition macrocyclization in flow at elevated temperature, could be rationalized in terms of the strain energy in the macrocyclic product. The progressive increase in strain resulting from reduction in macrocycle ring size, or the introduction of additional conformational constraints, results in marked deviations from typical geometries. These strained cyclophane macrocyclic systems provide access to spatial orientations of functionality that would not be readily available in unstrained or acyclic analogs. The most strained system prepared represents the first report of an 11-membered cyclophane containing a 1,4-disubstituted 1,2,3-triazole ring and establishes a limit to the ring strain that can be generated using this macrocycle synthesis methodology.

  DOI：

  10.1021/ja208503y
• 作为产物：
  描述：

  Boc-beta-丙氨酸 、 麻黄碱 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到tert-butyl (3-(((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)(methyl)amino)-3-oxopropyl)carbamate
  参考文献：
  名称：

  Strained Cyclophane Macrocycles: Impact of Progressive Ring Size Reduction on Synthesis and Structure

  摘要：

  The synthesis, X-ray, crystal structures, and calculated strain energies are reported for a homologous series of 11- to 14-membered drug-like cyclophane macrocycles, representing an unusual region of chemical space that can be difficult to access synthetically. The ratio of macrocycle to dimer, generated via a copper catalyzed azide-alkyne cycloaddition macrocyclization in flow at elevated temperature, could be rationalized in terms of the strain energy in the macrocyclic product. The progressive increase in strain resulting from reduction in macrocycle ring size, or the introduction of additional conformational constraints, results in marked deviations from typical geometries. These strained cyclophane macrocyclic systems provide access to spatial orientations of functionality that would not be readily available in unstrained or acyclic analogs. The most strained system prepared represents the first report of an 11-membered cyclophane containing a 1,4-disubstituted 1,2,3-triazole ring and establishes a limit to the ring strain that can be generated using this macrocycle synthesis methodology.

  DOI：

  10.1021/ja208503y