N-(2-ethoxy-2-oxoethylidene)methylamine N-oxide | 81206-61-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-ethoxy-2-oxoethylidene)methylamine N-oxide
• 英文别名: C-ethoxycarbonyl-N-methylnitrone；2-ethoxy-N-methyl-2-oxoethanimine oxide
• CAS: 81206-61-3
• 化学式: C₅H₉NO₃
• 分子量: 131.131
• InChiKey: DHVKJXUIAIUEJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-ethoxy-2-oxoethylidene)methylamine N-oxide 在 bis(acetonitrile)((S)-TolBINAP)paladium di(tetrafluoroborate) 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 120.0h， 生成 (R)-2-Methyl-5,5-diphenyl-isoxazolidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Kinetic Resolution of Isoxazolidines by a Pd−BINAP Complex

  摘要：

  Asymmetric decomposition of isoxazolidine derivatives under catalysis by optically active palladium(ii) complexes was examined. When racemic ethyl cis-2,5-dimethyl-5-phenylisoxazolidine-3-carboxylate (cis-1a) was treated with a catalytic amount of [Pd(MeCN)(2){(S)-TolBINAP}](BF4)2 in CH2Cl2 for 60 h, optically active substrate was recovered with 99% ee and in 48% yield. The highest selectivity was achieved on treatment of racemic ethyl trans-2,4-dimethyl-5,5-diphenylisoxazolidine-3-carboxylate, to give the optically active substrate in 74% yield with 35% ee. The k(f)/k(s) value of this reaction reaches as high as 732. For this decomposition, each substrate should have both a methyl group on the 2-position and an alkoxycarbonyl group on the 3-position of the isoxazolidine ring. The enantioselectivities of the recovered substrates were influenced not only by the other substituent groups on the 4- and 5-positions but also by the geometrical structures of the substrates.

  DOI：

  10.1002/1099-0690(200211)2002:22<3855::aid-ejoc3855>3.0.co;2-4
• 作为产物：
  描述：

  乙醛酸乙酯 、 N-甲基羟胺 在 碳酸氢钠 作用下， 以 甲苯 为溶剂， 生成 N-(2-ethoxy-2-oxoethylidene)methylamine N-oxide
  参考文献：
  名称：

  唾液酸及其衍生物的三步合成。

  摘要：

  DOI：

  10.1002/anie.200601555

文献信息

• BPh₃-Catalyzed [2+3] Cycloaddition of Ph₃PCCO with Aldonitrones: Access to 5-Isoxazolidinones with Exocyclic Phosphonium Ylide Moieties
  作者：Amandeep Brar、Daniel K. Unruh、Natalie Ling、Clemens Krempner

  DOI：10.1021/acs.orglett.9b02192

  日期：2019.8.16

  exocyclic phosphonium ylide functionalities via [2+3] cycloaddition of Ph3PCCO and aldonitrones has been developed and applied in the synthesis of 4-alkylidene-5-isoxazolidinones via Wittig olefination. The reaction proceeds by BPh3 catalysis under mild conditions and with a broad substrate scope. A reaction pathway involving the activation of the aldonitrone via interactions with the Lewis acid BPh3 is

  已经开发了一种通过Ph 3 PCCO和醛基酮的[2 + 3]环加成反应生成具有环外磷鎓叶立德官能团的5-异恶唑烷酮的方法，并将其用于通过Wittig烯烃合成4-亚烷基-5-异恶唑烷酮的方法。反应在温和的条件下，在较宽的底物范围内通过BPh 3催化进行。提出了一种通过与路易斯酸BPh 3相互作用来激活醛基亚硝基的反应途径。
• Steroidal [16.alpha.,17-d]isoxazolidines
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04018774A1

  公开（公告）日：1977-04-19

  Novel steroids having the structure ##STR1## and the 1,2-dehydro derivatives thereof, wherein R.sub.1 is hydrogen, hydroxy, alkanoyloxy, fluorine, chlorine, or bromine; R.sub.2 is alkyl or aryl; R.sub.3 is alkyl, aryl, alkanoyl, aroyl, alkoxycarbonyl, or cyano; R.sub.4 is hydrogen, alkyl, or aryl; R.sub.5 is hydrogen, fluorine or methyl; R.sub.6 is carbonyl, .beta.-hydroxymethylene, or .beta.-chloromethylene; R.sub.7 is hydrogen or methyl; and R.sub.8 is fluorine or chlorine; have useful anti-inflammatory activity.

  新型类固醇具有结构##STR1##及其1,2-脱氢衍生物，其中R.sub.1为氢、羟基、烷酰氧基、氟、氯或溴；R.sub.2为烷基或芳基；R.sub.3为烷基、芳基、烷酰基、芳酰基、烷氧羰基或氰基；R.sub.4为氢、烷基或芳基；R.sub.5为氢、氟或甲基；R.sub.6为羰基、β-羟甲烯基或β-氯甲烯基；R.sub.7为氢或甲基；R.sub.8为氟或氯；具有有用的抗炎活性。
• C−H Activation and Cross‐Coupling of Acyclic Aldonitrone
  作者：Jakub Brześkiewicz、Barbara Stańska、Piotr Dąbrowski、Rafał Loska

  DOI：10.1002/ejoc.202001496

  日期：2021.2.5

  Palladium‐catalyzed C(sp2)−H activation of an acyclic, glyoxalate‐derived aldonitrone and its cross‐coupling with a variety of aryl and heteroaryl bromides provides C‐aryl ketonitrones with very high E selectivity.

  钯催化的无环乙二醛基乙二醛腈的C（sp 2）-H活化及其与各种芳基和杂芳基溴化物的交叉偶联为C-芳基酮硝酮提供了很高的E选择性。
• Synthesis and X-ray study of hexahydro- and tetrahydrophospholo-[2,3-<i>d</i>]isoxazoles, a new class of heterocycles of potential fungicidal activity
  作者：Fabrizio Machetti、Beatrice Anichini、Stefano Cicchi、Alberto Brandi、Wanda Wieczorek、K. Michal Pietrusiewicz、Jean-Claude Gehret

  DOI：10.1002/jhet.5570330416

  日期：1996.7

  Hexahydro-, 5b-1 and 6a,f,1 and tetrahydrophospholo[2,3-d]isoxazoles 8, 9 and 10 were synthesized by 1,3-dipolar cycloaddition of nitrones 3b-1 and benzonitrile oxide (4) to 2,3-dihydro-1-phenyl-1H-phosphole 1-oxide (1) and 2,3-dihydro-1-ethoxy-1H-phosphole 1-oxide (2). The structural assignment to the compounds was confirmed by an X-ray study of two compounds of the series 5a and 5m. The compounds

  通过将1,3-偶极环3b-1和氧化苄腈（4）进行1,3-偶极环加成反应合成六氢，5b-1和6a，f，1和四氢磷[2,3- d ]异恶唑8、9和10。 3-二氢-1-苯基-1 H-磷酰基1-氧化物（1）和2，3-二氢-1-乙氧基-1 H-磷酰基1-氧化物（2）。通过对5a和5m系列的两种化合物的X射线研究证实了这些化合物的结构归属。该化合物作为杀真菌剂对葡萄小单胞菌表现出良好的活性。葡萄藤上和苹果上的灰葡萄孢菌。化合物5a-d显示出弱至中等的除草剂活性。
• A Novel Class of Modified Nucleosides: Synthesis of Alkylidene Isoxazolidinyl Nucleosides Containing Thymine
  作者：Anna Piperno、Antonio Rescifina、Antonino Corsaro、Maria A. Chiacchio、Antonio Procopio、Roberto Romeo

  DOI：10.1002/ejoc.200600817

  日期：2007.3

  The synthesis of hitherto unknown 1-[3-(hydroxymethyl)-2-methyl-4-methyleneisoxazolidin-5-yl]thymine (5), 1-(Z)-[3-(hydroxymethyl)-2-methylisoxazolidin-4-ylidene]methyl}thymine (6), and 1-(E)-[3-(hydroxymethyl)-2-methylisoxazolidin-5-ylidene]methyl}thymine (7) is described. The first compound can be regarded as a N,O-analogue of Entecavir and DMDC, which contains thymine as a nucleobase. The key

  迄今为止未知的1-[3-(羟甲基)-2-甲基-4-亚甲基异恶唑烷-5-基]胸腺嘧啶(5)、1-(Z)-[3-(羟甲基)-2-甲基异恶唑烷-4的合成描述了-亚基]甲基}胸腺嘧啶(6)和1-(E)-[3-(羟甲基)-2-甲基异恶唑烷-5-亚基]甲基}胸腺嘧啶(7)。第一种化合物可被视为恩替卡韦和 DMDC 的 N,O-类似物，其中含有胸腺嘧啶作为核碱基。从 2,3-二溴丙烯开始，以良好的收率制备了关键的丙二烯核碱基。随后的 1,3-偶极环加成以良好的位点选择性进行，得到 5 和区域异构核苷 6 和 7。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2007）