(E)-4-methoxy-4-oxobut-2-en-1-yl 4-methoxybenzoate | 957146-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4-methoxy-4-oxobut-2-en-1-yl 4-methoxybenzoate
• 英文别名: [(E)-4-methoxy-4-oxobut-2-enyl] 4-methoxybenzoate
• CAS: 957146-89-3
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: ZICFNKHDXVPJSZ-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-4-methoxy-4-oxobut-2-en-1-yl 4-methoxybenzoate 在 potassium osmate(VI) dihydrate 、 1,3-二氯-5,5-二甲基海因 、 4-甲基苯磺酸吡啶 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 sodium hydroxide 作用下， 以 丙醇 、 水 、 甲苯 为溶剂， 反应 4.0h， 生成 (4R,5S)-3-tert-butyl 5-methyl 4-((4-methoxybenzoyloxy)methyl)-2,2-dimethyloxazolidine-3,5-dicarboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of the Butyrolactone and the Oxazoline/Furan Fragment of Leupyrrin A₁

  摘要：

  Stereoselective syntheses of the Northern and the Southern fragments 2 and 3 of leupyrrin A(1) are reported. The convergent preparation of 2 is highlighted by a zirconocene-mediated one-pot cyclization-regioselective opening of an advanced diyne while the route to 3 involves a Krische allylation and a one-pot Sharpless dihydroxylation-cyclization. Comparison of the spectroscopic data with those reported for the natural product supports a relative stereochemical assignment within these heterocycles.

  DOI：

  10.1021/ol401110x
• 作为产物：
  描述：

  对甲氧基苯甲酰氯 在 4-二甲氨基吡啶 、 四氧化锇 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (E)-4-methoxy-4-oxobut-2-en-1-yl 4-methoxybenzoate
  参考文献：
  名称：

  Stereoselective Synthesis of the Butyrolactone and the Oxazoline/Furan Fragment of Leupyrrin A₁

  摘要：

  Stereoselective syntheses of the Northern and the Southern fragments 2 and 3 of leupyrrin A(1) are reported. The convergent preparation of 2 is highlighted by a zirconocene-mediated one-pot cyclization-regioselective opening of an advanced diyne while the route to 3 involves a Krische allylation and a one-pot Sharpless dihydroxylation-cyclization. Comparison of the spectroscopic data with those reported for the natural product supports a relative stereochemical assignment within these heterocycles.

  DOI：

  10.1021/ol401110x

文献信息

• [EN] TRANSITION METAL-CATALYZED IMIDATION OF ARENES<br/>[FR] IMIDATION D'ARÈNES CATALYSÉE PAR DES MÉTAUX DE TRANSITION
  申请人：HARVARD COLLEGE

  公开号：WO2015031725A1

  公开（公告）日：2015-03-05

  The present invention provides novel transition metal complexes (e.g., complexes of any one of Formulae (C1) to (C25)) that include an amine-N-oxide motif. The invention also provides methods of using these transition metal complexes in preparing N-aryl or N- heteroaryl sulfonimides (e.g., compounds of Formula (I)) and aryl or heteroaryl amines (e.g., compounds of Formula (II)). The inventive methods involve imidation of arenes and heteroarenes (e.g., compounds of Formula (A)) using an imidating agent (e.g., a compound of Formula (B), such as N-fluorobenzenesulfonimide (NFBS or NFSI)) in the presence of a single-electron reductant (e.g., an Ag(I) or Ru(II) salt).

  本发明提供了新型过渡金属配合物（例如，任一公式（C1）至（C25）中的配合物），其中包括胺-N-氧化物基团。该发明还提供了使用这些过渡金属配合物制备N-芳基或N-杂芳基磺酰亚胺（例如，公式（I）中的化合物）和芳基或杂芳基胺（例如，公式（II）中的化合物）的方法。创新方法涉及使用一种咪唑化试剂（例如，公式（B）中的化合物，如N-氟苯磺酰亚胺（NFBS或NFSI））在单电子还原剂（例如，Ag(I)或Ru(II)盐）存在下对芳烃和杂芳烃（例如，公式（A）中的化合物）进行咪唑化。
• The enantioselective synthesis of APTO and AETD: polyhydroxylated β-amino acid constituents of the microsclerodermin cyclic peptides
  作者：Emily C. Shuter、Hung Duong、Craig A. Hutton、Malcolm D. McLeod

  DOI：10.1039/b707891a

  日期：——

  The polyhydroxylated beta-amino acids (2S,3R,4S,5S,7E)-3-amino-8-phenyl-2,4,5-trihydroxyoct-7-enoic acid (APTO) and (2S,3R,4S,5S,7E,9E)-3-amino-10-(4-ethoxyphenyl)-2,4,5-trihydroxydeca-7,9-dienoic acid (AETD) are key components of the microsclerodermin family of anti-fungal cyclic peptides. They have been synthesised in protected form in twelve steps using a unified strategy, with the introduction

  多羟基化的β-氨基酸（2S，3R，4S，5S，7E）-3-氨基-8-苯基-2,4,5-三羟基辛-7-烯酸（APTO）和（2S，3R，4S，5S ，7E，9E）-3-氨基-10-（4-乙氧基苯基）-2,4,5-三羟基癸-7,9-二烯酸（AETD）是抗真菌环状肽微菌皮家族的关键成分。它们已使用统一策略以十二个步骤以保护形式合成，并在合成的最后一步中从常见的醛中间体引入不饱和侧链。合成的特征是不对称氨基羟基化和二羟基化反应的有序应用，以高选择性有效地引入了靶标的立体化学。
• Discovery of Selective Nanomolar Inhibitors for Insulin-Regulated Aminopeptidase Based on α-Hydroxy-β-amino Acid Derivatives of Bestatin
  作者：Dionisios Vourloumis、Ioannis Mavridis、Alexandros Athanasoulis、Ioannis Temponeras、Despoina Koumantou、Petros Giastas、Anastasia Mpakali、Victoria Magrioti、Jacqueline Leib、Peter van Endert、Efstratios Stratikos、Athanasios Papakyriakou

  DOI：10.1021/acs.jmedchem.2c00904

  日期：2022.7.28

  The oxytocinase subfamily of M1 zinc aminopeptidases comprises emerging drug targets, including the ER-resident aminopeptidases 1 and 2 (ERAP1 and ERAP2) and insulin-regulated aminopeptidase (IRAP); however, reports on clinically relevant inhibitors are limited. Here we report a new synthetic approach of high diastereo- and regioselectivity for functionalization of the α-hydroxy-β-amino acid scaffold

  M1 锌氨肽酶的催产素酶亚家族包括新兴的药物靶点，包括 ER 驻留氨肽酶 1 和 2（ERAP1 和 ERAP2）和胰岛素调节氨肽酶（IRAP）；然而，关于临床相关抑制剂的报道有限。在这里，我们报告了一种新的合成方法，该方法具有高非对映选择性和区域选择性，可用于 bestatin 的 α-羟基-β-氨基酸支架的功能化。通过与微摩尔抑制剂复合的 ERAP1 的高分辨率 X 射线晶体结构研究了立体化学和抑制机制。通过探索 P1 侧链功能，我们获得了显着的效力和选择性，并且我们报告了一种具有细胞活性的低纳摩尔 IRAP 抑制剂，其选择性比同源酶高 120 倍以上。IRAP 与该抑制剂复合的 X 射线晶体学分析表明，与 GAMEN 环的相互作用是效力和选择性的一个未被认可的关键决定因素。总体而言，我们的结果表明，α-羟基-β-氨基酸衍生物可能构成这组氨肽酶的有用化学工具和药物先导物。
• Pd-Catalyzed Aryl C–H Imidation with Arene as the Limiting Reagent
  作者：Gregory B. Boursalian、Ming-Yu Ngai、Katarzyna N. Hojczyk、Tobias Ritter

  DOI：10.1021/ja4064926

  日期：2013.9.11

  An amine-N-oxide-ligated palladium complex, in conjunction with a silver cocatalyst, catalyzes imidation of arenes by the reagent N-fluorobenzenesulfonimide. The reaction enables imidation of a variety of arenes at or below room temperature, requires no coordinating directing group on the substrate, and gives synthetically useful yields with only 1 equiv of arene. Mechanistic data implicate an unusual mechanism devoid of commonly invoked organometallic intermediates: oxidation of the Pd catalyst occurs as the turnover-limiting step, while C-H bond functionalization occurs subsequently at a high oxidation state of the catalyst.
• Stereoselective Synthesis of the Butyrolactone and the Oxazoline/Furan Fragment of Leupyrrin A₁
  作者：Thomas Debnar、Tongtong Wang、Dirk Menche

  DOI：10.1021/ol401110x

  日期：2013.6.7

  Stereoselective syntheses of the Northern and the Southern fragments 2 and 3 of leupyrrin A(1) are reported. The convergent preparation of 2 is highlighted by a zirconocene-mediated one-pot cyclization-regioselective opening of an advanced diyne while the route to 3 involves a Krische allylation and a one-pot Sharpless dihydroxylation-cyclization. Comparison of the spectroscopic data with those reported for the natural product supports a relative stereochemical assignment within these heterocycles.