(2S,4S)-2-tert-Butyl-4-isopropyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester | 182149-08-2

• 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: (2S,4S)-2-tert-Butyl-4-isopropyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester
• CAS: 182149-08-2
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: OPSLPNZIQCELCU-JQWIXIFHSA-N

物化性质

• 沸点：
  374.3±42.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,4S)-2-tert-Butyl-4-isopropyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester 在 氢氧化钾 、 四(三苯基膦)钯 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 5,5-二甲基-1,3-环己二酮 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 37.0h， 生成 (S)-2-Benzyloxycarbonylamino-3-methyl-2-(2-oxo-ethyl)-butyric acid methyl ester
  参考文献：
  名称：

  Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics

  摘要：

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.

  DOI：

  10.1021/ol0476974
• 作为产物：
  描述：

  L-缬氨酸 、 特戊醛 、 氯甲酸烯丙酯 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 正戊烷 、 二氯甲烷 为溶剂， 反应 458.0h， 以85%的产率得到(2S,4S)-2-tert-Butyl-4-isopropyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester
  参考文献：
  名称：

  Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics

  摘要：

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.

  DOI：

  10.1021/ol0476974

文献信息

• The design and synthesis of 2,5-linked pyrrolinones. A potential non-peptide peptidomimetic scaffold
  作者：Amos B Smith、Steven D Knight、Paul A Sprengeler、Ralph Hirschmann

  DOI：10.1016/0968-0896(96)00094-6

  日期：1996.7

  The de novo design and initial synthetic studies directed toward construction of a novel non-peptide scaffold for beta-strand/sheet and related secondary peptide structural mimics are described. The scaffold, consisting of a repeating array of 2,5,5-trisubstituted pyrrolinone (enaminone) units punctuated with appropriate amino acid side chains, is conceptually related to our previously successful 3,5-linked polypyrrolinone non-peptide peptidomimetic scaffold. Construction of the 2,5,5-trisubstituted pyrrolinone ring system proceeds via intramolecular condensation of an N-protected amino dione. The latter is prepared from a protected cl-amino ketone and aldehyde via an aldol-oxidation reaction sequence. Copyright (C) 1996 Elsevier Science Ltd