trans-α,β-epoxyhexanoic acid

• 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: trans-α,β-epoxyhexanoic acid
• 英文别名: trans-2,3-Epoxyhexanoic acid；(2R,3S)-3-propyloxirane-2-carboxylic acid
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: ZUXGVGARWYYZKY-CRCLSJGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-α,β-epoxyhexanoic acid 在 indium(III) chloride 、 sodium tetrahydroborate 、 sodium iodide 作用下， 以 水 为溶剂， 反应 0.5h， 生成 3-羟基己酸
  参考文献：
  名称：

  Bromolysis and Iodolysis of α,β-Epoxycarboxylic Acids in Water Catalyzed by Indium Halides

  摘要：

  The ring opening of alpha,beta -epoxycarboxylic acids by bromide and iodide ions has been efficiently carried out in water in high regio- and stereoselective fashion. The iodolysis of trans-beta -monoalkylated epoxycarboxylic acids at pH 4.0 was completely ol-regioselective and anti diastereoselective. The InCl3-catalyzed iodolysis of a variety of alpha,beta -epoxycarboxylic acids at pH 1.5 gave the corresponding anti beta -iodohydrins in 88-95% yields. The one-pot synthesis of the alpha- and beta -hydroxyhexanoic acids, starting from the corresponding alpha,beta -epoxycarboxylic acid 1a by iodolysis followed by reduction of the resulting iodohydrins 4a and 4b by NaBH4-InCl3 in water, has been performed.

  DOI：

  10.1021/jo0156215
• 作为产物：
  描述：

  (2RS,5RS,6SR)-5-bromo-6-propyl-2-phenyl-[1,3]oxazinan-4-one 在 4-二甲氨基吡啶 、 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 trans-α,β-epoxyhexanoic acid
  参考文献：
  名称：

  Convergent synthesis of cis-α,β-epoxy-carboxylic acids from 1-halo-2-trimethylsilyloxy-3-aza-4-phenyl-1,3-butadiene

  摘要：

  Reaction of a wide variety of aldehydes with the easily prepared 2-azadienes, in the presence of BF3 etherate, furnishes the corresponding hetero Diels-Alder adducts which have been converted, mainly, to cis epoxides via N-Boc protection followed by one-pot two-step ring opening and nucleophilic displacement of the halogen atom, resulting in final formation of an oxirane ling. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.019

文献信息

• New chiral amino alcohol ligands for catalytic enantioselective addition of diethylzincs to aldehydes
  作者：Carla Sappino、Alessandra Mari、Agnese Mantineo、Mauro Moliterno、Matteo Palagri、Chiara Tatangelo、Lorenza Suber、Paolo Bovicelli、Alessandra Ricelli、Giuliana Righi

  DOI：10.1039/c8ob00165k

  日期：——

  applicability as chiral catalysts was evaluated by carrying out the same reaction on a family of aldehydes, including variously substituted aromatic ones as well as an aliphatic analogue. The results have confirmed the validity of the fine-tuning process performed on ligands 13a and 13b. In fact, both exhibited excellent catalytic activity as demonstrated by the chemical yields and ee obtained from all the

  已经进行了旨在合成和优化具有适合于固定在磁铁矿纳米颗粒上的结构的新型，光学活性的β-氨基醇配体的结构的研究。优化的均相氨基醇催化剂13a和13b的手性来自合适的烯丙醇的Sharpless环氧化反应，通过使用公认的对映选择性氨基醇促进的二乙基锌与苯甲醛的加成反应进行测试，得到相应的苯甲醇，收率基本定量，ee = 95％。然后，通过对一系列醛，包括各种取代的芳族醛以及脂族类似物进行相同的反应，评估了它们作为手性催化剂的广泛适用性。结果证实了对配体13a和13b进行的微调过程的有效性。。实际上，如从化学产率和从所有测试的醛获得的ee所证实的，两者均显示出优异的催化活性，几乎与芳环中取代的位置和类型无关。
• Synthesis of optically active 1,4-benzoxazinones and 1,5-benzoxazepinones by regiocontrolled ring transformations of oxirane carboxylic acids and esters with aromatic o-hydroxyarylamines
  作者：Karsten Woydowski、Jürgen Liebscher

  DOI：10.1016/s0040-4020(99)00488-3

  日期：1999.7

  o-aminophenols 2 either to 1,4-benzoxazin-2-ones 5 or to the 1,5-benzoxazepin-2-one 4 while a condensed 1,4-oxazin-3-one 6 was obtained with 2-amino-3-hydroxypyridine. On the other hand optical active oxirane carboxylic acids 7 react with o-aminophenols8 in the presence of DCC (dicyclohexylcarbodiimide) or isobutyl chloroformiate affording oxirane carboxamides 9 that can be ring transformed to either 2,3-dihydro-4H-1

  对映体二乙基环氧乙烷乙烷二羧酸酯1与邻氨基苯酚2反应生成1,4-苯并恶嗪-2-酮5或与1,5-苯并恶唑啉-2-酮4反应，而缩合的1,4-恶嗪-3-酮6反应。用2-氨基-3-羟基吡啶制得。另一方面，光学活性环氧乙烷羧酸7在DCC（二环己基碳二亚胺）或氯甲酸异丁酯的存在下与邻氨基苯酚8反应，得到环氧乙烷羧酰胺9，其可以被环转化为2,3-二氢-4 H -1,4。 -苯并恶嗪-3-酮10或3-羟基-2,3-二氢-5H -1,5-苯并恶唑啉-4-酮11取决于反应条件。
• Harnessing the Chemical Activation Inherent to Carrier Protein-Bound Thioesters for the Characterization of Lipopeptide Fatty Acid Tailoring Enzymes
  作者：Florian Kopp、Uwe Linne、Markus Oberthür、Mohamed A. Marahiel

  DOI：10.1021/ja078081n

  日期：2008.2.1

  report a new experimental approach utilizing an amide ligation reaction for the characterization of acyl carrier protein (ACP)-bound reaction intermediates, which are otherwise difficult to analyze by traditional biochemical methods. To explore fatty acid tailoring enzymes of the calcium-dependent antibiotic (CDA) biosynthetic pathway, this strategy enabled the transformation of modified fatty acids, covalently

  在这里，我们报告了一种新的实验方法，该方法利用酰胺连接反应来表征酰基载体蛋白 (ACP) 结合的反应中间体，否则传统生化方法很难对其进行分析。为了探索钙依赖性抗生素 (CDA) 生物合成途径的脂肪酸定制酶，该策略能够将修饰的脂肪酸（以硫酯的形式与 ACP 共价结合）转化为可直接分析并与合成标准品进行比较的酰胺连接产物通过 HPLC-MS。酰胺形成的驱动力是硫酯结合化合物固有的热力学活化。使用这种新方法，我们能够表征 ACP 介导的 CDA 独特 2,3-环氧己酰基部分的生物合成，揭示了一种具有内在烯酰 ACP 环氧酶活性的新型 FAD 依赖性氧化酶 HxcO，以及第二种烯酰 ACP 环氧酶 HcmO。一般来说，我们的方法应该广泛适用于作用于载体蛋白的其他生物合成系统的体外表征，例如来自 NRPS 和 PKS 装配线的集成酶或脂肪和氨基酸前体合成的定制酶。
• 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。