(E)-ethyl 3-(N-oxypyridin-2-yl)acrylate | 90922-50-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-ethyl 3-(N-oxypyridin-2-yl)acrylate
• 英文别名: ethyl 3-(pyridin-2-yl)acrylate N-oxide；3-(1-oxy-pyridin-2-yl)-acrylic acid ethyl ester；3t-(1-oxy-[2]pyridyl)-acrylic acid ethyl ester；3t-(1-Oxy-[2]pyridyl)-acrylsaeure-aethylester；3-Pyridyl-(2)-acrylsaeure-ethylester-N-oxid；Ethyl 3-(2-Pyridinyl)acrylate, N-Oxide；ethyl (E)-3-(1-oxidopyridin-1-ium-2-yl)prop-2-enoate
• CAS: 90922-50-2
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: UNFGPZXTXRKHKH-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-(N-oxypyridin-2-yl)acrylate 在 palladium on activated charcoal Hydroquinone 1,4-phthalazinediyl diether 、 K2 、 氢气 、 potassium hexacyanoferrate(III) 作用下， 以 甲醇 、 水 、 三乙胺 、 叔丁醇 为溶剂， 反应 48.0h， 生成 (1S,2R,8aS)-hexahydro-1,2-dihydroxyindolizin-3(5H)-one
  参考文献：
  名称：

  A novel concise total synthesis of (+)-lentiginosine

  摘要：

  A total synthesis of (+)-lentiginosine was achieved by using ethyl 3-(pyridin-2-yl)acrylate N-oxide as the starting material and an improved Sharpless asymmetric dihydroxylation as the key step. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02606-0
• 作为产物：
  描述：

  3-吡啶-2-基丙-2-烯酸 在 乙醇 、 硫酸 、 双氧水 、 溶剂黄146 作用下， 生成 (E)-ethyl 3-(N-oxypyridin-2-yl)acrylate
  参考文献：
  名称：

  Katritzky et al., Journal of the Chemical Society, 1958, p. 3721

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed C−H Functionalization of Pyridine <i>N</i>-Oxides: Highly Selective Alkenylation and Direct Arylation with Unactivated Arenes
  作者：Seung Hwan Cho、Seung Jun Hwang、Sukbok Chang

  DOI：10.1021/ja8026295

  日期：2008.7.1

  Two catalytic protocols of the oxidative C-C bond formation have been developed on the basis of the C-H bond activation of pyridine N-oxides. Pd-catalyzed alkenylation of the N-oxides proceeds with excellent regio-, stereo-, and chemoselectivity, and the corresponding ortho-alkenylated N-oxide derivatives are obtained in good to excellent yields. Direct cross-coupling reaction of pyridine N-oxides

  在吡啶 N-氧化物的 CH 键活化的基础上开发了两种氧化 CC 键形成的催化方案。Pd 催化的 N-氧化物的烯基化以优异的区域选择性、立体选择性和化学选择性进行，并且相应的邻位烯基化 N-氧化物衍生物以良好到优异的产率获得。在 Pd 催化剂和 Ag 氧化剂的存在下，还开发了吡啶 N-氧化物与未活化芳烃的直接交叉偶联反应，这提供了具有高位点选择性的邻芳基化吡啶 N-氧化物产物。
• Asymmetric Aminohydroxylation of Heteroaromatic Acrylates
  作者：Dirk Raatz、Clara Innertsberger、Oliver Reiser

  DOI：10.1055/s-1999-2973

  日期：1999.12

  N-, S- and O-heteroaromatic acrylates were aminohydroxylated with generally high regio- and enantioselectivity. While pyridylacrylates are not amenable towards this process, the corresponding N-oxides proved to be a useful substitute, allowing the access to biologically important pyridine substituted taxolTM side chain analogs.

  N-、S-和O-杂 heteroaromatic 丙烯酸酯以通常较高的区域选择性和对映选择性进行了氨基羟基化。虽然吡啶丙烯酸酯不适合此过程，但相应的N-氧化物证明是一个有用的替代品，使得获得生物重要的吡啶取代的紫杉醇侧链类似物成为可能。
• Stereoselective synthesis of swainsonines from pyridines
  作者：Gerres Heimgärtner、Dirk Raatz、Oliver Reiser

  DOI：10.1016/j.tet.2004.10.086

  日期：2005.1

  efficient synthesis of (−)-swainsonine and (−)-2,8a-di-epi-swainsonine was developed starting from readily available 2-pyridinecarbaldehyde and 3-hydroxypyridine. In particular, it was demonstrated that the mixture of simple indolizidines, i.e. lentiginosine and epi-lentiginosine, being readily available by a number of different synthetic routes, can be directly converted to swainsonine.

  从容易获得的2-吡啶甲醛和3-羟基吡啶开始开发了一种有效合成（-）-swainsonine和（-）-2,8a-di- epi -swainsonine的方法。特别地，已经证明，可以通过许多不同的合成途径容易获得的简单的吲哚嗪核苷的混合物，即龙胆草碱和表-龙胆草碱，可以直接转化成猪wa碱。
• Asymmetric dihydroxylation of heteroaromatic acrylates
  作者：Zhi-Xiang Feng、Wei-Shan Zhou

  DOI：10.1016/s0040-4039(02)02605-9

  日期：2003.1

  N- and O-Heteroaromatic acrylates were dihydroxylated with high ee's and good yields. While the AD of pyridyl and pyrryl acrylates afforded diverse yields under the present reaction condition, some corresponding N-substituted pyridyl and pyrryl acrylates (1d, 1e, 1g) proved to be appropriate substrates. The diols obtained can be used as chiral building blocks for the synthesis of various biologically active molecules. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Katritzky et al., Journal of the Chemical Society, 1958, p. 3721
  作者：Katritzky et al.

  DOI：——

  日期：——