3-乙基-3-羟基戊酸甲酯 | 74126-51-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3-乙基-3-羟基戊酸甲酯
• 英文名称: methyl 3-ethyl-3-hydroxypentanoate
• CAS: 74126-51-5
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: WYUTVGUNUTYAAE-UHFFFAOYSA-N

物化性质

• 沸点：
  80 °C(Press: 11 Torr)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  3-乙基-3-羟基戊酸甲酯 在 四氯化碳 、 乙醇 、 五氯化磷 、 氨 作用下， 生成 甲基3-乙基-2-戊烯酸酯
  参考文献：
  名称：

  Philippi; Hendgen; Hernler, Monatshefte fur Chemie, 1936, vol. 69, p. 279

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 3-ethyl-3-hydroxypentanoate 在 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 3-乙基-3-羟基戊酸甲酯
  参考文献：
  名称：

  Bifunctional even-electron ions. III. Fragmentation behaviour of aliphatic hydroxonium ions containing an additional carbomethoxy group

  摘要：

  AbstractThe primary and subsequent fragmentations of the bifunctional oxonium ions \documentclass{article}\pagestyle{empty}\begin{document}${\rm R} \!-\! \mathop {\rm C}\limits^ + ({\rm OH})\! -\! ({\rm CH}_2)_n \! - \! {\rm COOCH}_3 $\end{document} (n = 0−5), a, are dominated by functional group interactions. Loss of CH3OH is the only appreciable primary fragmentation of the higher homoiogues, but for the lowest homologue (a0) this reaction is missing. Instead, CO loss is observed. The next homologue (a1) shov.s loss of CH2CO besides loss of CH3OH. The mode of the subsequent fragmentations is dependent on the chain length separating the functional group, and formation of cyclic ions is typical of the fragmentation behaviour of a2 and a3. Evidence for proton transfer from the carbonyl oxygen to the methoxy group of a protonated ester group is presented.

  DOI：

  10.1002/oms.1210230202

文献信息

• Hydroxy-Directed Amidation of Carboxylic Acid Esters Using a Tantalum Alkoxide Catalyst
  作者：Hiroaki Tsuji、Hisashi Yamamoto

  DOI：10.1021/jacs.6b09482

  日期：2016.11.2

  the chemoselective synthesis of amides by using a metal-catalyzed hydroxy-directed reaction. A hydroxy group located at the β-position of an ester group promoted the activation of a carbonyl group with a tantalum alkoxide catalyst followed by amidation reactions, leading to a wide variety of β-hydroxyamides with excellent chemeselectivity. The chemoselective amidation strategy can be extended to the

  我们在此描述了一种通过使用金属催化的羟基定向反应化学选择性合成酰胺的新策略。位于酯基 β 位的羟基促进了羰基在烷氧基钽催化剂下的活化，随后进行了酰胺化反应，从而产生了多种具有优异化学选择性的 β-羟基酰胺。化学选择性酰胺化策略可以扩展到二肽衍生物的催化合成，这在现代有机合成中仍然是具有挑战性的研究课题。
• Iron-Catalysed Reformatsky-Type Reactions
  作者：Muriel Durandetti、Jacques Périchon

  DOI：10.1055/s-2006-926432

  日期：2006.5

  A Reformatsky-type reaction has been developed using iron catalysis in acetonitrile or DMF. Reduction of iron(II) bromide by manganese metal in acetonitrile provides a low-valent iron catalyst, which is the active species; under these conditions, α-chloroesters or nitriles can both be converted into their corresponding derivatives. The method was applicable to both ketones and aldehydes, resulting in the formation of β-hydroxyesters under mild conditions.

  一种 Reformatsky 型反应已采用铁催化体系在乙腈或二甲基甲酰胺中得到开发。通过在乙腈中用锰金属还原二溴化铁，可得到低价铁催化剂，该催化剂为活性物种；在这些条件下，α-氯酯或腈均可转化为相应的衍生物。该方法适用于酮和醛，在温和条件下形成 β-羟基酯。
• Electroreductive coupling of methallylchloride or methyl chloroacetate with carbonyl compounds catalyzed by nickel bipyridine complexes
  作者：Soline Sibille、Esther d'Incan、Louis Leport、Marie-Claude Massebiau、Jacques Perichon

  DOI：10.1016/s0040-4039(00)95647-8

  日期：1987.1

  β-hydroxy esters in the presence of catalytic amounts of the NiBr2(2,2′-bipyridine) complex has been developped from mixed electrolysis of methallylchloride, or methylchloroacetate with several carbonyl compounds, using a one-compartment cell equiped of a sacrificial zinc anode.

  已经开发了一种在催化量的NiBr 2（2,2'-联吡啶）络合物存在下有效地电合成均烯丙基醇或β-羟基酯的方法，该方法是将甲代烯丙基氯或甲基氯乙酸酯与几种羰基化合物混合电解，装有牺牲锌阳极的隔室。
• Ni-catalyzed activation of α-chloroesters: a simple method for the synthesis of α-arylesters and β-hydroxyesters
  作者：Muriel Durandetti、Corinne Gosmini、Jacques Périchon

  DOI：10.1016/j.tet.2006.11.055

  日期：2007.1

  Coupling reactions of α-chloroesters with aryl halides (α-arylation) or carbonyl compounds (Reformatsky) using nickel catalyst allow, under mild conditions, the preparation of various functionalized aryl propionic acid derivatives or β-hydroxyesters. In the synthesis of aryl propionic acid derivatives, the process is efficient with aryl halides bearing either electron-withdrawing or electron-donating

  使用镍催化剂，α-氯酸酯与芳基卤化物（α-芳基化）或羰基化合物（Reformatsky）的偶联反应可以在温和的条件下制备各种官能化的芳基丙酸衍生物或β-羟基酯。在芳基丙酸衍生物的合成中，该方法对于带有带吸电子基团或给电子基团的芳基卤化物是有效的。
• Substrate specificity of farnesylpyrophosphate synthetase. Application to asymmetric synthesis
  作者：Tanetoshi Koyama、Akio Saito、Kyozo Ogura、Shuichi Seto

  DOI：10.1021/ja00530a050

  日期：1980.5