(S)-4-Acetoxy-3-methyl-butyric acid | 108772-88-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-4-Acetoxy-3-methyl-butyric acid
• 英文别名: (3S)-4-acetyloxy-3-methylbutanoic acid
• CAS: 108772-88-9
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: UUQIWHALPNBOMN-YFKPBYRVSA-N

物化性质

• 沸点：
  276.8±23.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-4-Acetoxy-3-methyl-butyric acid 在 sodium hydroxide 作用下， 以 水 为溶剂， 以0.517 g的产率得到DL-3-甲基-Γ-丁内酯
  参考文献：
  名称：

  光学活性β-烷基取代的γ-内酯和威士忌内酯类似物的合成和嗅觉评价

  摘要：

  合成了具有光学活性的β-烷基取代的γ-内酯和威士忌内酯类似物，并评估了其气味特性。在手性中间体的制备过程中，我们发现了3-芳基甲基-2-甲基-1-丙醇的高度对映选择性酯化反应的良好反应条件，以动力学方式将它们拆分。合成内酯的嗅觉评价结果表明，γ-内酯环上的烷基对气味分布起重要作用。

  DOI：

  10.1016/j.tet.2020.130984
• 作为产物：
  描述：

  (S)-β-methyl-2-thiophenepropanol acetate 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 6.0h， 以300 mg的产率得到(S)-4-Acetoxy-3-methyl-butyric acid
  参考文献：
  名称：

  Bakers' yeast reduction of thiophenepropaenals. Enantioselective synthesis of (S)-2-methyl-1-alkanols via bakers' yeast mediated reduction of 2-methyl-3-(2-thiophene)propenals

  摘要：

  DOI：

  10.1021/jo00033a028

文献信息

• Asymmetric hydrogenation of unsaturated carboxylic acids catalyzed by BINAP-ruthenium(II) complexes
  作者：Tetsuo Ohta、Hidemasa Takaya、Masato Kitamura、Katsunori Nagai、Ryoji Noyori

  DOI：10.1021/jo00390a043

  日期：1987.7
• Metathesis for catalyst design: metacatalysis
  作者：Sakunchai Khumsubdee、Kevin Burgess

  DOI：10.1016/j.tet.2013.12.040

  日期：2014.2

  Prior studies have shown an effective way to produce diverse ligand sets for catalyst discovery is by using mixtures of monodentate forms to generate catalysts in situ. Research described here was performed to illustrate that alkene-functionalized monodentate ligands could be used in this way and in another that increases the diversity of the ligand library in an interesting way. Specifically, we hypothesized that as well as being used as monomers, these alkenes could be cross metathesized in situ immediately before the catalysis step. This combination of metathesis to form ligands in situ, then catalysis is referred to here as metacatalysis. In the event, a library of quinidine and quinine alkaloid-derived phosphites were tested as mixtures of monomers and dimers formed via metathesis in situ. The data obtained illustrated that metacatalysis can be used to identify ligands that positively and negatively modulate enantioselectivities in iridium-mediated hydrogenations of a,alpha,beta-unsaturated carboxylic acid derivatives, relative to the mixtures of the monomeric forms used. (C) 2014 Elsevier Ltd. All rights reserved.