(R)-methyl 2-hydroxy-3,3-dimethylbutanoate | 40348-85-4

• 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: (R)-methyl 2-hydroxy-3,3-dimethylbutanoate
• 英文别名: methyl (R)-2-hydroxy-3,3-dimethylbutanoate；methyl 2-hydroxy-3,3-dimethylbutanoate；methyl 3,3-dimethyl-2-hydroxybutanoate；methyl(2R)-2-hydroxy-3,3-dimethylbutanoate；methyl (2R)-2-hydroxy-3,3-dimethylbutanoate
• CAS: 40348-85-4
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: YYAKMBGOMGURAY-YFKPBYRVSA-N

物化性质

• 沸点：
  161.8±8.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-hydroxy-3,3-dimethylbutanoate 在 咪唑 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 2-碘酰基苯甲酸 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 24.42h， 生成 (2S,6S,E)-2-((tert-butyldimethylsilyl)oxy)-7,7-dimethyl-6-((triethylsilyl)oxy)oct-4-en-1-ol
  参考文献：
  名称：

  使用手性 Horner-Wittig 试剂和双功能醛作为关键构建模块正式合成巴斯蒂莫内酯 A

  摘要：

  [显示省略]

  DOI：

  10.1016/j.tchem.2024.100065
• 作为产物：
  描述：

  2-(1-R-benzyloxy-2,2-dimethylpropyl)-1,3-oxathiane 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 12.0h， 生成 (R)-methyl 2-hydroxy-3,3-dimethylbutanoate
  参考文献：
  名称：

  基于1,3-氧杂蒽3̄的不对称反应：仲α-羟基酸，RCHOHCO 2 H和二醇RCHOHCH 2 OH

  摘要：

  减少先前准备的1（+）-普勒高酮与各种金属氢化物的混合物衍生的手性2-酰基-1,3-氧杂蒽基化合物进行立体选择性反应，在用三仲锂还原苯基酮的情况下，非对映体过量（de）高达97％丁基硼氢化物。伯或叔烷基酮的选择性较低（最大为82％de）：主要的非对映异构体易于通过色谱法纯化。在这些情况下，主要产品是克拉姆的螯合法则所预测的。产物比率用氢化二异丁基丁基铝反转，并且在仲锂还原仲烷基酮中也是如此。丁基硼氢化物，立体选择性低。用N-氯代琥珀酰亚胺-硝酸银将2-羟烷基-1,3-氧杂蒽基裂解为α-羟醛，并将醛还原为乙二醇RCHOHCH 2OH与硼氢化钠很少或没有外消旋作用。酯类，RCHOHCO 2 CH 3，是通过在裂解之前对2-羟基烷基-1,3-氧杂蒽基进行O-苄基化，裂解后用亚氯酸钠氧化，酯化和脱苄基而获得的高对映体纯度。一种通过将苯甲醛转化为2-苯基-1,3-二氧戊环并随后对所得的2-苯基-4-烷基-1

  DOI：

  10.1016/s0040-4020(01)82419-4

文献信息

• Effect of aggregation on stereochemistry and mechanism of asymmetric oxidation of the lithium enolate of methyl 3,3-dimethylbutanoate in the solid state and in solution
  作者：Wei Yen、R. Bakthavatchalam、Jin Xian-Ming、Christopher K. Murphy、Franklin A. Davis

  DOI：10.1016/s0040-4039(00)79208-2

  日期：1993.6

  Oxidation of the title enolate by enantiopure (camphorylsulfonyl)oxaziridines in THF afforded α-hydroxyester with 53–73% ee, but the product from the solid state reactions was racemic. The results suggest that the enolate exists and reacts as an aggregate in the solid state reactions.

  对映体（樟脑磺酰基）恶氮丙啶在THF中氧化标题烯醇化物可得到ee值为53-73％的α-羟基酯，但固态反应的产物是外消旋的。结果表明，烯醇化物以固态反应形式存在并以聚集体形式反应。
• Enantiomeric Inclusion of α-Hydroxy Esters by (<i>R</i>)-(1-Naphthyl)glycyl-(<i>R</i>)-phenylglycine and the Crystal Structures of the Inclusion Cavities
  作者：Motohiro Akazome、Toshiaki Takahashi、Katsuyuki Ogura

  DOI：10.1021/jo9818778

  日期：1999.4.1

  A simple dipeptide, (R)-(l-naphthyl)glycyl-(R)-phenylglycine [(R,R)-1], formed inclusion compounds with several alpha-hydroxy esters (2) with high enantioselectivity. By crystallization of a mixture of the dipeptide [(R,R)-1] and racemic 2a [MeCH(OH)COOMe] from methanol, asymmetric recognition occurred to give an inclusion compound that contains the S form of 2a in 89% ee: X-ray crystallographic study of the inclusion compound elucidated that the dipeptide molecules arrange in a "folded antiparallel" beta-sheetlike structure to accommodate the alpha-hydroxy ester in the pocket-type cavity surrounded by naphthyl and phenyl groups on the sheet. Similarly, 2b [MeCH(OH)COOEt] and 2f [dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone] were included with high enantioselectivity of the S form. When bulkier 2l [t-BuCH(OH)COOMe] was used as a guest molecule, the arrangement of dipeptide molecules changed to an "extended antiparallel" mode, where the naphthyl and phenyl groups arranged in a "parallel stacked and displaced" mode and a channel-type cavity was constructed. The guest molecules were accommodated via hydrogen bonding in the channel-type cavity with high enantioselectivity of the S form (82% ee). In the case of 2k [i-PrCH(OH)COOMe], optically pure (S)-2k formed the dipeptide sheet with the "folded antiparallel" structure by cocrystallization with (R,R)-1, while the "extended antiparallel" structure appeared in the inclusion of racemic 2k.
• Reduction by a model of NAD(P)H. 25. A chiral model which induces high asymmetry
  作者：Atsuyoshi Ohno、Masahiko Ikeguchi、Takahide Kimura、Shinzaburo Oka

  DOI：10.1021/ja00517a043

  日期：1979.11
• Asymmetric reduction of .alpha.-keto esters with potassium 9-O-(1,2:5,6-di-O-isopropylidene-.alpha.-D-glucofuranose)-9-boratabicyclo[3.3.1]nonane. Chiral synthesis of .alpha.-hydroxy esters with optical purity approaching 100% ee
  作者：Herbert C. Brown、Byung Tae Cho、Won Suh Park

  DOI：10.1021/jo00367a038

  日期：1986.8
• Asymmetric oxygenation of chiral imide enolates. A general approach to the synthesis of enantiomerically pure .alpha.-hydroxy carboxylic acid synthons
  作者：D. A. Evans、M. M. Morrissey、R. L. Dorow

  DOI：10.1021/ja00300a054

  日期：1985.7