ethyl 3-n-propyloxiranecarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: ethyl 3-n-propyloxiranecarboxylate
• 英文别名: Ethyl trans-3-propyloxirane-2-carboxylate；(+/-)-threo-2,3-epoxy-hexanoic acid ethyl ester；(+/-)-threo-2,3-Epoxy-hexansaeure-aethylester；Ethyl (2R,3S)-3-propyl-2-oxiranecarboxylate；ethyl (2R,3S)-3-propyloxirane-2-carboxylate
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: MRUCFECRMITDHC-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-n-propyloxiranecarboxylate 在 sodium phenylseleno(triethyl)borate 作用下， 以 乙醇 为溶剂， 反应 0.33h， 生成 3-羟基己酸乙酯
  参考文献：
  名称：

  Organoselenium-mediated Reduction of α, β-Epoxy Esters to β-Hydroxy Esters

  摘要：

  使用有机硒试剂 Na+[PhSeB(OEt)3]-，通过 α 取代过程将 α、β-环氧酯还原为 β-羟基酯。

  DOI：

  10.1246/cl.1988.507
• 作为产物：
  描述：

  反式-2-己烯酸乙酯 在 4,4'-硫联二(6-叔丁基-2-甲基苯酚) 、 间氯过氧苯甲酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以73%的产率得到ethyl 3-n-propyloxiranecarboxylate
  参考文献：
  名称：

  氮丙啶-2-羧酸酯的便捷合成

  摘要：

  用叠氮化钠处理由使用Sharpless环氧化的烯丙基醇制备的旋光环氧乙烷-2-羧酸酯。随后通过与三苯基膦反应以高收率和高光学纯度将获得的叠氮基醇转化为氮丙啶-2-羧酸酯。使各种外消旋环氧乙烷-2-羧酸酯进行相同的反应顺序。

  DOI：

  10.1002/recl.19921110101

文献信息

• Organic Reactions Catalyzed by Methylrhenium Trioxide:  Reactions of Ethyl Diazoacetate and Organic Azides
  作者：Zuolin Zhu、James H. Espenson

  DOI：10.1021/ja954039t

  日期：1996.1.1

  para position of phenols favors the formation of α-phenoxy ethyl acetates. The use of EDA to form α-thio ethyl acetates and N-substituted glycine ethyl esters, on the other hand, is hardly affected by the size or structure of the parent thiol or amine, with all of these reactions proceeding in high yield. MTO-catalyzed cycloaddition reactions occur between EDA and aromatic imines, olefins, and carbonyl

  三氧化甲基铼（CH3ReO3 或 MTO）催化重氮乙酸乙酯 EDA 的几类反应。它是第一个用于卡宾转移的高价氧配合物。在温和的条件下，在没有其他底物的情况下，EDA 被转化为马来酸二乙酯和富马酸二乙酯的 9:1 混合物。在醇的存在下，以良好的收率获得了α-烷氧基乙酸乙酯。更大和更多支化醇的产率下降，材料的平衡是马来酸二乙酯和富马酸二乙酯。苯酚对位的给电子基团有利于α-苯氧基乙酸乙酯的形成。另一方面，使用 EDA 形成 α-硫代乙酸乙酯和 N-取代的甘氨酸乙酯几乎不受母体硫醇或胺的大小或结构的影响，所有这些反应都以高产率进行。MTO 催化的环加成反应发生在 EDA 和芳族亚胺、烯烃和羰基化合物之间。形成三元环产物：氮丙啶、环...
• Dimethyl carbonate in the regio- and stereocontrolled opening of three-membered heterocyclic rings
  作者：Giuliana Righi、Paolo Bovicelli、Maurizio Barontini、Ilaria Tirotta

  DOI：10.1039/c2gc16241e

  日期：——

  In an attempt to replace harmful or carcinogenic solvents (such as dichloromethane, acetone, etc.) with non-harmful and greener ones, the possibility of performing four already developed ring-opening methodologies in a more eco-friendly media, such as DMC, has been investigated. The results show that the usual employed solvents (CH2Cl2, Et2O, CH3CN, etc.) can be easily replaced by DMC: not only the stereo- and regioselectivity is conserved, but also the work-up is simplified to a filtration, therefore reducing considerably the amount of solvents employed in the processes, and all the reactions are performed at room temperature, even the ones previously reported at low temperatures.

  为了用无害和更环保的溶剂取代有害或致癌溶剂（如二氯甲烷、丙酮等），研究人员研究了在更环保的介质（如 DMC）中进行四种已开发的开环方法的可能性。结果表明，通常使用的溶剂（CH2Cl2、Et2O、CH3CN 等）可以很容易地被 DMC 取代：不仅立体选择性和区域选择性得以保留，而且工作过程简化为过滤，从而大大减少了过程中使用的溶剂量，而且所有反应都是在室温下进行的，甚至包括以前报道过的在低温下进行的反应。
• Process for production of optically active-3-amino-2-hydroxypropionic cyclopropylamide derivatives and salts thereof
  申请人：Mori Kohei

  公开号：US20100048909A1

  公开（公告）日：2010-02-25

  An objective of the present application is to provide an industrially practicable method for producing an optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof from an inexpensive easily-available starting material. The derivative or salt thereof is useful as an intermediate for a medicine. It is also intended by the present application to provide a useful intermediate of the derivative. The objective is attained by the following method. First, an easily-available 2-halo-3-oxopropionic acid derivative is asymmetrically reduced, and then epoxidated to produce an optically-active epoxycarboxylic acid derivative. Next, the derivative is converted into an optically-active epoxyamide derivative by reaction with cyclopropylamine, and then reacted with a nitrile to obtain an optically-active oxazolinamide derivative. Subsequently, selective acid solvolysis of the oxazoline skeleton gives the optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof.

  本申请的目标是提供一种工业实用的方法，从廉价易得的起始物质中生产出光学活性的3-氨基-2-羟基丙酸环丙酰胺衍生物或其盐。该衍生物或其盐可用作药物的中间体。本申请还旨在提供该衍生物的有用中间体。该目标通过以下方法实现。首先，对易得的2-卤代-3-酮丙酸衍生物进行不对称还原，然后环氧化，以产生光学活性的环氧羧酸衍生物。接下来，通过与环丙胺反应将该衍生物转化为光学活性的环氧酰胺衍生物，然后与腈反应得到光学活性的噁唑烷酰胺衍生物。随后，对噁唑烷骨架进行选择性酸性溶解，得到光学活性的3-氨基-2-羟基丙酸环丙酰胺衍生物或其盐。
• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE 3-AMINO-2 -HYDROXYPROPIONIC CYCLOPROPYLAMIDE DERIVATIVES AND SALTS THEREOF
  申请人：Kaneka Corporation

  公开号：EP2039689A1

  公开（公告）日：2009-03-25

  An objective of the present application is to provide an industrially practicable method for producing an optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof from an inexpensive easily-available starting material. The derivative or salt thereof is useful as an intermediate for a medicine. It is also intended by the present application to provide a useful intermediate of the derivative. The objective is attained by the following method. First, an easily-available 2-halo-3-oxopropionic acid derivative is asymmetrically reduced, and then epoxidated to produce an optically-active epoxycarboxylic acid derivative. Next, the derivative is converted into an optically-active epoxyamide derivative by reaction with cyclopropylamine, and then reacted with a nitrile to obtain an optically-active oxazolinamide derivative. Subsequently, selective acid solvolysis of the oxazoline skeleton gives the optically-active 3-amino-2-hydroxypropionic cyclopropylamide derivative or salt thereof.

  本申请的目的是提供一种工业上可行的方法，利用廉价易得的起始原料生产具有光学活性的 3-氨基-2-羟基丙酰基环丙基酰胺衍生物或其盐。该衍生物或其盐可用作药物的中间体。本申请的另一个目的是提供一种有用的衍生物中间体。通过以下方法可以达到目的。首先，将一种易得的 2-卤代-3-氧代丙酸衍生物进行不对称还原，然后环氧化，生成一种具有光学活性的环氧羧酸衍生物。接着，该衍生物与环丙胺反应转化为光学活性环氧酰胺衍生物，然后与腈反应得到光学活性噁唑啉酰胺衍生物。随后，对噁唑啉骨架进行选择性酸溶解，得到具有光学活性的 3-氨基-2-羟基丙酸环丙基酰胺衍生物或其盐。
• EP2039689
  申请人：——

  公开号：——

  公开（公告）日：——