(S)-4-(allyloxy)-2-hydroxy-4-oxobutanoic acid | 1248798-63-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (S)-4-(allyloxy)-2-hydroxy-4-oxobutanoic acid
• 英文别名: (2S)-2-hydroxy-4-oxo-4-prop-2-enoxybutanoic acid
• CAS: 1248798-63-1
• 化学式: C₇H₁₀O₅
• 分子量: 174.153
• InChiKey: XCFFWFTVRMHJEX-YFKPBYRVSA-N

物化性质

• 沸点：
  364.7±32.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-叔丁基-1,3-二异丙基异脲 、 (S)-4-(allyloxy)-2-hydroxy-4-oxobutanoic acid 以 二氯甲烷 为溶剂， 以2.94 g的产率得到4-allyl 1-tert-butyl (2S)-hydroxysuccinate
  参考文献：
  名称：

  Approaches for the Synthesis of Functionalized Cryptophycins

  摘要：

  The first syntheses of bioactive cryptophycins functionalized at unit ID were accomplished ina one-pot Staudinger reduction/cyclization step An a/ado precursor for the lower part of the backbone was introduced to minimize protective group chemistry and enable a very convenient synthesis of cryptophycin-52 and unit D eryptophycin analogues containing an ester or a free carboxylic acid for bioconjugations Both new cryptophycin derivatives show high biological activity in cytotoxicity assays

  DOI：

  10.1021/jo101563s
• 作为产物：
  描述：

  L-天冬氨酸,4-(2-丙烯基)酯,盐酸 在 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 (S)-4-(allyloxy)-2-hydroxy-4-oxobutanoic acid
  参考文献：
  名称：

  Approaches for the Synthesis of Functionalized Cryptophycins

  摘要：

  The first syntheses of bioactive cryptophycins functionalized at unit ID were accomplished ina one-pot Staudinger reduction/cyclization step An a/ado precursor for the lower part of the backbone was introduced to minimize protective group chemistry and enable a very convenient synthesis of cryptophycin-52 and unit D eryptophycin analogues containing an ester or a free carboxylic acid for bioconjugations Both new cryptophycin derivatives show high biological activity in cytotoxicity assays

  DOI：

  10.1021/jo101563s

文献信息

• Amide-to-Ester Substitution Allows Fine-Tuning of the Cyclopeptide Conformational Ensemble
  作者：Tommaso Cupido、Jan Spengler、Javier Ruiz-Rodriguez、Jaume Adan、Francesc Mitjans、Jaume Piulats、Fernando Albericio

  DOI：10.1002/anie.200907274

  日期：2010.4.1

  Without affecting the overall 3D structure, amide‐to‐ester backbone substitution (or ester scan) exerts a pronounced influence on the conformational equilibrium of the RGD cyclopeptide cilengitide and its derivatives (see figure; RGD=Arg‐Gly‐Asp). The appropriate substitution, which stabilized the receptor‐complementary conformations, improved the biological activity of this integrin antagonist.

  在不影响整体3D结构的情况下，酰胺至酯主链取代（或酯扫描）对RGD环肽cilengitide及其衍生物的构象平衡产生显着影响（见图； RGD = Arg-Gly-Asp）。适当的取代可稳定受体互补构象，从而改善了这种整合素拮抗剂的生物活性。