(S)-2-[N-((R)-3-Acetyl-2-oxo-oxazolidine-4-carbonyl)-N'-tert-butoxycarbonyl-hydrazino]-4-[1,3]dioxolan-2-yl-butyric acid methyl ester | 200338-29-0

• 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: (S)-2-[N-((R)-3-Acetyl-2-oxo-oxazolidine-4-carbonyl)-N'-tert-butoxycarbonyl-hydrazino]-4-[1,3]dioxolan-2-yl-butyric acid methyl ester
• CAS: 200338-29-0
• 化学式: C₁₉H₂₉N₃O₁₀
• 分子量: 459.453
• InChiKey: OLYFVKKBZSRXBJ-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  150.01
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[N-((R)-3-Acetyl-2-oxo-oxazolidine-4-carbonyl)-N'-tert-butoxycarbonyl-hydrazino]-4-[1,3]dioxolan-2-yl-butyric acid methyl ester 在 甲醇 、 4-二甲氨基吡啶 、 三乙胺 、 三氟乙酸 、 肼 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.5h， 生成 (S)-2-((R)-2-Amino-3-hydroxy-propionyl)-2,3,4,5-tetrahydro-pyridazine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Elevated Conformational Rigidity in Dipeptides Incorporating Piperazic Acid Derivatives

  摘要：

  N-Acyl derivatives of piperazic acids display an unusual degree of conformational rigidity. As a consequence, alpha-N-coupling of a piperazic acid of given configuration (D or L) with an alpha-aminoacyl unit of opposite configuration (L or D) produces a "heterochiral" dipeptide that exists in a conformation conducive to the formation of a peptide turn. Piperazic acids and related compounds may thus be regarded as conformationally rigid analogues of proline, and because they are readily available in either antipodal form by synthesis, they should become of great interest in the study of peptide turns.

  DOI：

  10.1021/ja9729903
• 作为产物：
  描述：

  (S)-4-benzyl-3-(5,5-ethylenedioxypentanoyl)-2-oxazolidinone 在 palladium on activated charcoal 2,4,6-三甲基吡啶 、 氢气 、 lithium diisopropyl amide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 13.36h， 生成 (S)-2-[N-((R)-3-Acetyl-2-oxo-oxazolidine-4-carbonyl)-N'-tert-butoxycarbonyl-hydrazino]-4-[1,3]dioxolan-2-yl-butyric acid methyl ester
  参考文献：
  名称：

  Elevated Conformational Rigidity in Dipeptides Incorporating Piperazic Acid Derivatives

  摘要：

  N-Acyl derivatives of piperazic acids display an unusual degree of conformational rigidity. As a consequence, alpha-N-coupling of a piperazic acid of given configuration (D or L) with an alpha-aminoacyl unit of opposite configuration (L or D) produces a "heterochiral" dipeptide that exists in a conformation conducive to the formation of a peptide turn. Piperazic acids and related compounds may thus be regarded as conformationally rigid analogues of proline, and because they are readily available in either antipodal form by synthesis, they should become of great interest in the study of peptide turns.

  DOI：

  10.1021/ja9729903

文献信息

• Elevated Conformational Rigidity in Dipeptides Incorporating Piperazic Acid Derivatives
  作者：Ning Xi、Lawrence B. Alemany、Marco A. Ciufolini

  DOI：10.1021/ja9729903

  日期：1998.1.1

  N-Acyl derivatives of piperazic acids display an unusual degree of conformational rigidity. As a consequence, alpha-N-coupling of a piperazic acid of given configuration (D or L) with an alpha-aminoacyl unit of opposite configuration (L or D) produces a "heterochiral" dipeptide that exists in a conformation conducive to the formation of a peptide turn. Piperazic acids and related compounds may thus be regarded as conformationally rigid analogues of proline, and because they are readily available in either antipodal form by synthesis, they should become of great interest in the study of peptide turns.