4-deoxy-erythronic acid ethyl ester | 89534-55-4

• 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: 4-deoxy-erythronic acid ethyl ester
• 英文别名: 4-Desoxy-erythronsaeure-aethylester；ethyl 2,3-dihydroxybutanoate
• CAS: 89534-55-4
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: PMNDLKWRJQBUCG-UHFFFAOYSA-N

物化性质

• 沸点：
  113 °C(Press: 10 Torr)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-deoxy-erythronic acid ethyl ester 在 三(2-氯乙基)胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 6.0h， 以78%的产率得到(2R,3R)-3-Azido-2-hydroxy-butyric acid ethyl ester
  参考文献：
  名称：

  Unusual Regioselection in the Mitsunobu Reactions of syn-2,3-Dihydroxy Esters:  Synthesis of Statine and Its Diastereomer

  摘要：

  Mitsunobu reactions of syn-2,3-dihydroxy esters exhibit a complete regioselection for the beta-hydroxyl group. Benzoylation, azidation, and tosylation have been performed under these conditions. beta-Functionalizations of syn-2,3-dihydroxy esters are uncommon, and the Mitsunobu reactions are complementary to other diol chemistries in the regioselection. In addition, the configurational inversion accompanying the Mitsunobu protocol offers a means for diastereochemical diversity, as exemplified by a synthesis of statine and its anti diastereomer. These findings will further expand the synthetic utilities of the Sharpless AD process.

  DOI：

  10.1021/jo015967f
• 作为产物：
  描述：

  反式-2-丁烯酸乙酯 在 potassium osmate(VI) 、 甲基三氧化铼(VII) N-甲基吗啉 、 双氧水 、 柠檬酸 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.0h， 以90%的产率得到4-deoxy-erythronic acid ethyl ester
  参考文献：
  名称：

  在酸性条件下用过氧化氢对Ol / R催化的烯烃进行二羟基化

  摘要：

  柠檬酸的简单添加赋予参与使用过氧化氢水溶液作为末端氧化剂的三重催化系统的催化活性和species物种很大的稳定性。所得体系能够以高收率将传统抗性烯烃二羟基化。

  DOI：

  10.1002/adsc.200303043

文献信息

• Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H2O2
  作者：Pattama Saisaha、Dirk Pijper、Ruben P. van Summeren、Rob Hoen、Christian Smit、Johannes W. de Boer、Ronald Hage、Paul L. Alsters、Ben L. Feringa、Wesley R. Browne

  DOI：10.1039/c0ob00102c

  日期：——

  A practical method for the multigram scale selective cis-dihydroxylation of electron deficient alkenes such as diethyl fumarate and N-alkyl and N-aryl-maleimides using H2O2 is described. High turnovers (>1000) can be achieved with this efficient manganese based catalyst system, prepared in situ from a manganese salt, pyridine-2-carboxylic acid, a ketone and a base, under ambient conditions. Under optimized conditions, for diethyl fumarate at least 1000 turnovers could be achieved with only 1.5 equiv. of H2O2 with d/l-diethyl tartrate (cis-diol product) as the sole product. For electron rich alkenes, such as cis-cyclooctene, this catalyst provides for efficient epoxidation.

  本文描述了一种实用方法，利用H2O2实现对多克规模电子缺失型烯烃（如富马酸二乙酯和N-烷基及N-芳基马来酰亚胺）的选择性顺式二羟基化。在该高效的锰基催化体系中，可在常温常压下，以高转化率（超过1000次）实现反应。该催化剂体系由锰盐、吡啶-2-羧酸、酮和碱在原位制备而成。在优化的条件下，富马酸二乙酯至少可实现1000次转化，仅使用1.5当量的 ，产物为唯一的（顺-二醇）d/l-酒石酸二乙酯。对于电子丰富的烯烃，如顺式-环辛烯，该催化剂可提供高效的环氧化作用。
• [EN] METHODS FOR PREPARING FLUOROALKYL ARYLSULFINYL COMPOUNDS AND FLUORINATED COMPOUNDS THERETO<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS FLUOROALKYLE ARYLSULFINYLÉS ET COMPOSÉS FLUORÉS APPARENTÉS
  申请人：IM & T RES INC

  公开号：WO2010022001A1

  公开（公告）日：2010-02-25

  Novel preparative methods for fluoroalkyl arylsulfinyl compounds are disclosed. Fluorinated compounds as useful fluorinated compounds, intermediates, or builing blocks are disclosed. Useful applications of the fluoroalkyl arylsulfinyl compounds are shown.

  揭示了用于制备氟烷基芳基磺酰基化合物的新型制备方法。公开了氟化合物作为有用的氟化合物、中间体或构建块。展示了氟烷基芳基磺酰基化合物的有用应用。
• General and Efficient α-Oxygenation of Carbonyl Compounds by TEMPO Induced by Single-Electron-Transfer Oxidation of Their Enolates
  作者：Emanuela Dinca、Philip Hartmann、Jakub Smrček、Ina Dix、Peter G. Jones、Ullrich Jahn

  DOI：10.1002/ejoc.201200736

  日期：2012.8

  for the synthesis of protected α-oxygenated carbonyl compounds is reported. It is based on the single-electron-transfer oxidation of easily generated enolates to the corresponding α-carbonyl radicals. Coupling with the stable free radical TEMPO provides α-(piperidinyloxy) ketones, esters, amides, acids or nitriles in moderate-to-excellent yields. Enolate aggregates influence the outcome of the oxygenation

  报道了一种普遍适用的合成受保护的 α-氧化羰基化合物的方法。它基于将容易生成的烯醇化物单电子转移氧化为相应的 α-羰基自由基。与稳定的自由基 TEMPO 结合以中等至优异的产率提供 α-(哌啶基氧基) 酮、酯、酰胺、酸或腈。烯醇化物聚集体显着影响氧化反应的结果。对竞争反应进行了分析，并提出了将其最小化的条件。产物的化学选择性还原导致 N-O 键裂解为 α-羟基羰基化合物或羰基官能团还原为单保护的 1,2-二醇或 O-保护的氨基醇。
• [EN] HETEROARYL COMPOUNDS AS SODIUM CHANNEL BLOCKERS<br/>[FR] COMPOSÉS HÉTÉROARYLIQUES COMME AGENTS DE BLOCAGE DES CANAUX SODIQUES
  申请人：PURDUE PHARMA LP

  公开号：WO2013064883A1

  公开（公告）日：2013-05-10

  The invention relates to aryl substituted compounds of Formula (I) : and pharmaceutically acceptable salts, prodrugs, or solvates thereof, wherein Het, G, A, R, and n are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula I to treat a disorder responsive to the blockade of sodium channels. Compounds of the present invention are especially useful for treating pain.

  该发明涉及公式（I）的芳基取代化合物及其药用可接受的盐、前药或溶剂化物，其中Het、G、A、R和n的定义如规范中所述。该发明还涉及使用公式I的化合物治疗对钠通道阻滞有反应的疾病。本发明的化合物特别适用于治疗疼痛。
• [EN] NEW INTERMEDIATE COMPOUND FOR PREPARING VITAMIN B6<br/>[FR] NOUVEAU COMPOSÉ INTERMÉDIAIRE POUR LA PRÉPARATION DE VITAMINE B6
  申请人：DSM IP ASSETS BV

  公开号：WO2013163889A1

  公开（公告）日：2013-11-07

  Provided is a new intermediate compound for preparing vitamin B6, which can be used to synthesize the known intermediate compound for preparing vitamin B6, 4-methyloxazole-5-carboxyLate. Further provided is a process for preparing the new intermediate compound and a process for preparing the known intermediate compound 4-methyloxazole-5-carboxylate from the new intermediate compound.

  提供了一种新的中间化合物，用于制备维生素B6，可用于合成用于制备维生素B6的已知中间化合物4-甲氧咪唑-5-羧酸。进一步提供了制备新中间化合物的方法以及从新中间化合物制备已知中间化合物4-甲氧咪唑-5-羧酸的方法。