4-methoxy-benzoic acid 2-oxo-ethyl ester | 422268-10-8

• 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: 4-methoxy-benzoic acid 2-oxo-ethyl ester
• 英文别名: 4-methoxybenzoic acid 2-oxo-ethyl ester；p-methoxybenzoyloxyacetaldehyde；2-oxoethyl 4-methoxybenzoate
• CAS: 422268-10-8
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: SPGDHFFXZRGQGP-UHFFFAOYSA-N

物化性质

• 沸点：
  337.0±22.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-benzoic acid 2-oxo-ethyl ester 在 potassium osmate(VI) dihydrate 、 正丁基锂 、 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 四氢呋喃 、 丙醇 、 正己烷 、 水 、 甲苯 为溶剂， 反应 4.5h， 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：

  4-methoxy-benzoic acid 2,2-diethoxy-ethyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.5h， 生成 4-methoxy-benzoic acid 2-oxo-ethyl ester
  参考文献：
  名称：

  Synthesis of (−)‐DAPD

  摘要：

  A new synthesis of (-)-DAPD, suitable for large scale development, is described.

  DOI：

  10.1081/ncn-200040643

文献信息

• Stereodivergent Dual Catalytic α‐Allylation of Protected α‐Amino‐ and α‐Hydroxyacetaldehydes
  作者：Tobias Sandmeier、Simon Krautwald、Hannes F. Zipfel、Erick M. Carreira

  DOI：10.1002/anie.201506933

  日期：2015.11.23

  Fully stereodivergent dual‐catalytic α‐allylation of protected α‐amino‐ and α‐hydroxyacetaldehydes is achieved through iridium‐ and amine‐catalyzed substitution of racemic allylic alcohols with chiral enamines generated in situ. The operationally simple method furnishes useful aldehyde building blocks in good yields, more than 99 % ee, and with d.r. values greater than 20:1 in some cases. Additionally

  通过铱和胺催化的外消旋烯丙基醇被原位生成的手性烯胺取代，可以实现受保护的α-氨基和α-羟基乙醛的完全立体发散双催化α-烯丙基化。该操作简单的方法可提供有用的醛结构单元，产率高，ee大于99％，并且在某些情况下其dr值大于20：1。此外，该γ，δ-不饱和产物，可以进一步在一个stereodivergent方式以高选择性和与立体化学完整性的保存在C官能α 位置。
• Methods to manufacture 1,3-dioxolane nucleosides
  申请人：Sznaidman Marcos

  公开号：US20060036092A1

  公开（公告）日：2006-02-16

  This application provides a process for preparing enantiomerically pure β-D-dioxolane nucleosides. In particular, a new synthesis of (−)-DAPD, suitable for large scale development, is described. In one embodiment the invention provides a process for preparing a substantially pure β-D- or β-L-1,3-dioxolane nucleosides comprising a) preparing or obtaining an esterified 2,2-dialkoxy ethanol; b) cyclizing the esterified 2,2-dialkoxy ethanol with glycolic acid to obtain a 1,3-dioxolane lactone; c) resolving the 1,3-dioxolane lactone to obtain a substantially pure D- or L-lactone; d) selectively reducing and activating the D- or L-chiral lactone to obtain a substantially pure D- or L-1,3-dioxolane; e) coupling the D- or L-1,3-dioxolane to an activated and/or protected purine or pyrimidine base; and f) optionally purifying the nucleoside to obtain a substantially pure protected β-D- or P-L-1,3-dioxolane nucleoside.

  该应用程序提供了一种制备对映纯β-D-二氧杂环核苷的方法。具体来说，描述了一种适用于大规模开发的新合成方法，用于制备(−)-DAPD。在一种实施方式中，该发明提供了一种制备基本纯β-D-或β-L-1,3-二氧杂环核苷的方法，包括a) 制备或获取酯化的2,2-二烷氧基乙醇；b) 将酯化的2,2-二烷氧基乙醇与甘醇酸环化以获得1,3-二氧杂环内酯；c) 分解1,3-二氧杂环内酯以获得基本纯的D-或L-内酯；d) 选择性还原和激活D-或L-手性内酯以获得基本纯的D-或L-1,3-二氧杂环；e) 将D-或L-1,3-二氧杂环与激活和/或保护的嘌呤或嘧啶碱基偶联；f) 可选地纯化核苷以获得基本纯的保护的β-D-或P-L-1,3-二氧杂环核苷。
• Preparation of intermediates useful in the synthesis of antiviral nucleosides
  申请人：——

  公开号：US20030162992A1

  公开（公告）日：2003-08-28

  The present invention is an efficient process for the manufacture of &agr;-acyloxyacetaldehyde, a key intermediate in the synthesis of 1,3-oxathiolane and 1,3-dioxolane nucleosides.

  本发明是一种制备&agr;-酰氧基乙醛的高效过程，该化合物是合成1,3-噻二环己烷和1,3-二氧杂环己烷核苷的关键中间体。
• 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。
• Methods to Manufacture 1,3-Dioxolane Nucleosides
  申请人：Sznaidman Marcos

  公开号：US20110130559A1

  公开（公告）日：2011-06-02

  This application provides a process for preparing enantiomerically pure β-D-dioxolane nucleosides. In particular, a new synthesis of (−)-DAPD, suitable for large scale development, is described. In one embodiment the invention provides a process for preparing a substantially pure β-D- or β-L-1,3-dioxolane nucleosides comprising a) preparing or obtaining an esterified 2,2-dialkoxy ethanol; b) cyclizing the esterified 2,2-dialkoxy ethanol with glycolic acid to obtain a 1,3-dioxolane lactone; c) resolving the 1,3-dioxolane lactone to obtain a substantially pure D- or L-lactone; d) selectively reducing and activating the D- or L-chiral lactone to obtain a substantially pure D- or L-1,3-dioxolane; e) coupling the D- or L-1,3-dioxolane to an activated and/or protected purine or pyrimidine base; and f) optionally purifying the nucleoside to obtain a substantially pure protected β-D- or β-L-1,3-dioxolane nucleoside.

  该应用程序提供了一种制备对映纯的β-D-二氧杂环己烷核苷的方法。特别地，描述了一种适用于大规模开发的(−)-DAPD的新合成方法。在一种实施例中，该发明提供了一种制备基本纯的β-D-或β-L-1,3-二氧杂环己烷核苷的方法，包括a) 准备或获得酯化的2,2-二烷氧基乙醇; b) 用乙醇酸环化酯化的2,2-二烷氧基乙醇以获得1,3-二氧杂环己烷内酯; c) 分离1,3-二氧杂环己烷内酯以获得基本纯的D-或L-内酯; d) 选择性还原和激活D-或L-手性内酯以获得基本纯的D-或L-1,3-二氧杂环己烷; e) 将D-或L-1,3-二氧杂环己烷偶联到活化和/或保护的嘌呤或嘧啶碱基上; f) 可选地纯化核苷酸以获得基本纯的保护的β-D-或β-L-1,3-二氧杂环己烷核苷。