2-甲基-3-乙基-3-羟基丙酸甲酯 | 60665-94-3

• 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
• 中文名称: 2-甲基-3-乙基-3-羟基丙酸甲酯
• 英文名称: methyl 3-hydroxy-2-methylpentanoate
• 英文别名: methyl 2-methyl-3-ethyl-3-hydroxypropionate
• CAS: 60665-94-3
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: DPSANHWICFQPHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  4
• 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：

  2-甲基-3-乙基-3-羟基丙酸甲酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 反-2-甲基-2-戊烯酸甲酯
  参考文献：
  名称：

  Structure-Activity Relationships of Unsaturated Analogs of Valproic Acid

  摘要：

  The principal metabolite of valproic acid (VPA), 2-ene VPA, appears to share most of VPA's pharmacological and therapeutic properties while lacking its hepatotoxicity and teratogenicity, thus making it a useful lead compound for the development of safer antiepileptic drugs. Analogues of 2-ene VPA were evaluated for anticonvulsant activity in mice using the subcutaneous pentylenetetrazole test. Cyclooctylideneacetic acid exhibited a potency markedly exceeding that of VPA itself with only modest levels of sedation. Potency, as either ED(50) or brain concentration, was highly correlated (r > 0.85) with volume and lipophilicity rather than with one of the shape parameters calculated by molecular modeling techniques, arguing against the existence of a specific receptor site. Instead, a role for the plasma membrane in mediating the anticonvulsant effect is suggested.

  DOI：

  10.1021/jm00017a024
• 作为产物：
  描述：

  2-甲基-3-氧代戊酸甲酯 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以80%的产率得到2-甲基-3-乙基-3-羟基丙酸甲酯
  参考文献：
  名称：

  Stereoselective chemoenzymatic synthesis of sitophilate: a natural pheromone

  摘要：

  The aggregation pheromone of the granary weevil Sitophilus granarius, (2S,3R)-1-ethylpropyl 3-hydroxy-2-methylpentanoate, has been synthesized in 63% total isolated yield and high chemical and enantiomeric purity (98% de, > 99% ee) from readily available methyl 3-oxopentanoate. A stereoselective ketone reduction followed by an ester hydrolysis, were the two key steps of the synthesis and were both performed by commercially available enzymes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.008

文献信息

• Kinetics of the ring-opening carbonylation of ethyloxirane with hydrido tetracarbonyl cobalt
  作者：József Kreisz、Ferenc Ungváry、Attila Sisak、László Markó

  DOI：10.1016/0022-328x(91)80163-e

  日期：1991.10

  The rate of CO uptake in the reaction of HCo(CO)4 with ethyloxirane, which gives (3-hydroxypentanoyl)cobalt tetracarbonyl as the major product in an n-octane/methyl isobutyl ketone solvent mixture at 15° C, is first order with respect to HCo(CO)4 and ethyloxirane, and independent of the concentration of CO(CO)4−4 or CO. The reaction is faster with DCo(CO)4. A preequilibrium ion pair formation and a

  HCo（CO）4与乙基环氧乙烷反应的CO吸收速率是一阶的，其中环氧乙烷在15°C的正辛烷/甲基异丁基酮溶剂混合物中产生（3-羟基戊酰基）钴四羰基化合物为主要产物。尊重HCO（CO）4和乙基环氧乙烷，和独立CO（CO）的浓度的4 - 4或CO的反应是与DCO（CO）更快。4。导致这些结果的原因是，先形成了平衡离子对，然后进行了确定速率的内部取代反应，然后快速插入一氧化碳。
• Optically active compounding having plural chiral centers and production
  申请人：Chisso Corporation

  公开号：US05411877A1

  公开（公告）日：1995-05-02

  An ester is caused to act on a 2-substituted-3-hydroxycarboxylic acid ester as a racemate in the presence of hydrolase under substantially anhydrous conditions to effect a transesterification resulting in the resolution. The compound thus resolved is converted to an optically active 2,6-cis-2,5,6-substituted-1,3-dioxan-4-one and the resulting compound is recrystallized to give optically active 5,6-anti-2,5,6-substituted-1,3-dioxan-4-one and 5,6-syn-2,5,6-substituted-1,3-dioxan-4-one. Thus an optically active compound having plural chiral centers. Further, an optically active 2,5,6-substituted-1,3-dioxan-4-one obtained by transesterification and recrystallization is reacted with an alcohol to produce an optically active 2-substituted-3-hydroxycarboxylic acid ester.

  在基本无水的条件下，通过酯酶使酯作用于2-取代-3-羟基羧酸酯的外消旋体，以实现转酯反应并进行拆分。因此，被分离的化合物被转化为具有光学活性的2,6-顺式-2,5,6-取代-1,3-二氧杂环-4-酮，并且所得化合物被重结晶以得到具有光学活性的5,6-反-2,5,6-取代-1,3-二氧杂环-4-酮和5,6-顺-2,5,6-取代-1,3-二氧杂环-4-酮。因此，得到具有多个手性中心的光学活性化合物。此外，通过转酯反应和重结晶获得的光学活性2,5,6-取代-1,3-二氧杂环-4-酮与醇反应，产生光学活性的2-取代-3-羟基羧酸酯。
• Optically active compounds having plural chiral centers and production
  申请人：Chisso Corporation

  公开号：US05348870A1

  公开（公告）日：1994-09-20

  An ester is caused to act on a 2-substituted-3-hydroxycarboxylic acid ester as a racemate in the presence of hydrolase under substantially anhydrous conditions to effect a transesterification resulting in the resolution. The compound thus resolved is converted to an optically active 2,6-cis-2,5,6-substituted-1,3-dioxan-4-one and the resulting compound is recrystallized to give optically active 5,6-anti-2,5,6-substituted-1,3-dioxan-4-one and 5,6-syn-2,5,6-substituted-1,3-dioxan-4-one. Thus an optically active compound having plural chiral centers. Further, an optically active 2,5,6-substituted-1,3-dioxan-4-one obtained by transesterification and recrystallization is reacted with an alcohol to produce an optically active 2-substituted-3-hydroxycarboxylic acid ester.

  通过酯对2-取代-3-羟基羧酸酯进行消旋作用，存在水解酶的情况下，在基本无水的条件下发生转酯化反应，从而导致分辨过程。因此，分辨出的化合物被转化为具有光学活性的2,6-顺式-2,5,6-取代-1,3-二氧杂环戊酮，并且通过再结晶得到具有光学活性的5,6-反式-2,5,6-取代-1,3-二氧杂环戊酮和5,6-顺式-2,5,6-取代-1,3-二氧杂环戊酮。因此，得到了具有多个手性中心的光学活性化合物。此外，通过转酯化和再结晶得到的光学活性2,5,6-取代-1,3-二氧杂环戊酮与醇反应，可以产生光学活性的2-取代-3-羟基羧酸酯。
• Optically active compounds having plural chiral centers and the production thereof
  申请人：Chisso Corporation

  公开号：EP0428392A2

  公开（公告）日：1991-05-22

  Optically active compounds, having a plurality of chiral centres, have the general formulae: or in which R', R2 and R4 are the same or are different and each is an alkyl, alkenyl or alkynyl group having up to 40 carbon atoms, the carbon chain of which may contain one or more of halogen, cyano, oxygen, nitrogen, silicon, sulfur and substituted or unsubstituted benzene, cyclohexane, pyridine, pyrimidine, pyridazine, pyrazine, dioxane or bicyclooctane ring 5; R3 is an alkyl, alkenyl or alkynyl groups having 3 to 40 carbon atoms ; X is hydrogen or an alkanoyl group having 2 to 40 carbon atoms; and the carbon atom with the sign, *, is an asymmetic carbon.

  具有多个手性中心的光学活性化合物的通式为 或 其中 R'、R2 和 R4 相同或不同，且各自为具有多达 40 个碳原子的烷基、烯基或炔基，其碳链可包含一个或多个卤素、氰基、氧、氮、硅、硫和取代或未取代的苯、环己烷、吡啶、嘧啶、哒嗪、吡嗪、二氧杂环或双环辛烷环 5； R3 是具有 3 至 40 个碳原子的烷基、烯基或炔基； X 是氢或具有 2 至 40 个碳原子的烷酰基； 符号 * 的碳原子为异构碳。
• Process for the stereoselective transformation of a diol to an alcohol
  申请人：SEPRACOR, INC.

  公开号：EP0493187A1

  公开（公告）日：1992-07-01

  An efficient and commercially-viable method for the stereoselective transformation of a diol to an alcohol is disclosed. The present method is particularly well-suited for the preparation of the unnatural D-isomer of malic acid or its derivatives from the abundant naturally occurring L-tartaric acid or derivatives thereof.

  本发明公开了一种将二元醇立体选择性转化为醇的高效且商业上可行的方法。本方法特别适用于从丰富的天然 L-酒石酸或其衍生物中制备苹果酸或其衍生物的非天然 D-异构体。