methyl (S)-3-hydroxy-4,4-dimethyl-5-oxo-heptanoate | 331268-25-8

• 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: methyl (S)-3-hydroxy-4,4-dimethyl-5-oxo-heptanoate
• 英文别名: methyl (3S)-3-hydroxy-4,4-dimethyl-5-oxoheptanoate
• CAS: 331268-25-8
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: QQMKDEPDCGAPID-QMMMGPOBSA-N

物化性质

• 沸点：
  308.6±22.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (S)-3-hydroxy-4,4-dimethyl-5-oxo-heptanoate 在 2,6-二甲基吡啶 、 lithium hydroxide 、 三氟甲磺酸 、 四丁基氟化铵 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 环己烷 为溶剂， 反应 16.67h， 生成 (3S,6S,7R,8S,12Z,15S,16E)-7-[tert-butyl(dimethyl)silyl]oxy-15-hydroxy-3-[(4-methoxyphenyl)methoxy]-4,4,6,8,16-pentamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid
  参考文献：
  名称：

  Synthesis and Characterization of Upper and Lower Rim Functionalized [6]Cavitands

  摘要：

  A [6]cavitand has been selectively derivatized on both the lower and upper rims. On the lower rim, two out of six potential sites were oxidized to produce a 1,4 substituted [6]cavitand bisketone, which was converted to a corresponding diol as well as a bisacetate [6]cavitand. The crystal structures of the bisketone and the diol were solved. On the upper rim, all six ArCH3 groups were selectively brominated to ArCH2Br groups to produce the hexabromomethyl [6]cavitand, which was converted to the corresponding hexabenzylthiol and hexabenzylthioacetate [6]cavitands. The conformational properties of all compounds are discussed.

  DOI：

  10.1002/1521-3765(20020816)8:16<3717::aid-chem3717>3.0.co;2-g
• 作为产物：
  描述：

  在 dicobalt octacarbonyl 3-羟基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0~65.0 ℃ 、5.17 MPa 条件下， 反应 37.0h， 生成 methyl (S)-3-hydroxy-4,4-dimethyl-5-oxo-heptanoate
  参考文献：
  名称：

  Synthesis and Characterization of Upper and Lower Rim Functionalized [6]Cavitands

  摘要：

  A [6]cavitand has been selectively derivatized on both the lower and upper rims. On the lower rim, two out of six potential sites were oxidized to produce a 1,4 substituted [6]cavitand bisketone, which was converted to a corresponding diol as well as a bisacetate [6]cavitand. The crystal structures of the bisketone and the diol were solved. On the upper rim, all six ArCH3 groups were selectively brominated to ArCH2Br groups to produce the hexabromomethyl [6]cavitand, which was converted to the corresponding hexabenzylthiol and hexabenzylthioacetate [6]cavitands. The conformational properties of all compounds are discussed.

  DOI：

  10.1002/1521-3765(20020816)8:16<3717::aid-chem3717>3.0.co;2-g

文献信息

• The Total Synthesis of Epothilone D as a Yardstick for Probing New Methodologies
  作者：Alexander M. Haydl、Bernhard Breit

  DOI：10.1002/chem.201605011

  日期：2017.1.12

  includes the use of a previously reported enantiospecific zinc‐catalyzed cross‐coupling of an α‐hydroxy ester triflate with a Grignard reagent, the application of a hydroboration/boron–magnesium exchange sequence for the rapid construction of the Z‐substituted trisubstituted double bond present in the natural product, and a Noyori‐type hydrogenation to install the β‐hydroxy ester moiety of the southern part

  在此，研究了埃博霉素D的简洁且高度收敛的合成方法，该方法依赖于可以克级量级制备的等复杂度相同的片段。构建片段的策略包括使用先前报道的对映体特异性锌催化的三氟甲磺酸α-羟基酯与格利雅试剂的交叉偶联，氢硼化/硼-镁交换序列的应用以快速构建Z天然产物中存在预取代的三取代双键，并进行Noyori型氢化以安装南部的β-羟基酯部分。成功的关键是通过分子内添加相应的ω-炔基取代的羧酸在一个步骤中在大环核心结构中构建新的立体中心，从而实现非对映选择性的从头至尾的宏观内酯化。
• Synthesis and Characterization of Upper and Lower Rim Functionalized [6]Cavitands
  作者：Christoph Naumann、Brian O. Patrick、John Sherman

  DOI：10.1002/1521-3765(20020816)8:16<3717::aid-chem3717>3.0.co;2-g

  日期：2002.8.16

  A [6]cavitand has been selectively derivatized on both the lower and upper rims. On the lower rim, two out of six potential sites were oxidized to produce a 1,4 substituted [6]cavitand bisketone, which was converted to a corresponding diol as well as a bisacetate [6]cavitand. The crystal structures of the bisketone and the diol were solved. On the upper rim, all six ArCH3 groups were selectively brominated to ArCH2Br groups to produce the hexabromomethyl [6]cavitand, which was converted to the corresponding hexabenzylthiol and hexabenzylthioacetate [6]cavitands. The conformational properties of all compounds are discussed.