5-aza-5-carbobenzoxy-2-oxa-3-oxo-bicyclo<2.2.1>heptane | 80986-14-7

• 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: 5-aza-5-carbobenzoxy-2-oxa-3-oxo-bicyclo<2.2.1>heptane
• 英文别名: (1S,4S)-benzyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate；benzyl (1S,4S)-3-oxo-5-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate；cis-1-benzyloxycarbonyl-4-hydroxy-L-proline lactone；cis-1-Benzyloxycarbonyl-4-hydroxy-L-prolin-lacton；benzyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate
• CAS: 80986-14-7
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: COAKWHFMVQYSTL-QWRGUYRKSA-N

物化性质

• 沸点：
  450.2±45.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-aza-5-carbobenzoxy-2-oxa-3-oxo-bicyclo<2.2.1>heptane 在 咪唑 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 (2S,4S)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)pyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Developing microcolin A analogs as biological probes

  摘要：

  Three microcolin A and B analogs have been synthesized. Their biological activity profiles were evaluated against several cell lines, revealing the existence of a structural determinant whose role in mediating the antiproliferative effect of the microcolins has heretofore gone unrecognized. While previously described as potent immunosuppressive natural products, we found that these microcolin analogs possessed no selective cytotoxicity when comparing immune cell versus nonimmune cell proliferation. In addition, the amino-terminus of microcolin A has been modified to incorporate a biotinylated polyethylene glycol linker. The biological activity of this biotinylated microcolin A analog was determined. This affinity reagent was shown to retain limited biological activity and thus can serve as a useful probe for elucidating the mechanism of action of microcolin A. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.020
• 作为产物：
  描述：

  L-羟基脯氨酸 在 三苯基膦 、 sodium hydroxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 8.0h， 生成 5-aza-5-carbobenzoxy-2-oxa-3-oxo-bicyclo<2.2.1>heptane
  参考文献：
  名称：

  二苯基脯氨醇甲硅烷基醚衍生的硫脲作为醛向硝基烯烃不对称迈克尔加成反应的高效催化剂

  摘要：

  这封信描述了第一种由二芳基脯氨醇甲硅烷基醚衍生的双官能硫脲有机催化剂的合成。将催化剂应用于醛与硝基烯烃的不对称迈克尔加成反应，以良好的收率（高达99％ee）和出色的非对映选择性（高达99：1）以良好的收率（高达99％）得到所需的加合物。C-4取代基的空间位置对反应活性和立体选择性很重要。

  DOI：

  10.1016/j.tetlet.2015.04.119

文献信息

• A New Family of Conformationally Constrained Bicyclic Diarylprolinol Silyl Ethers as Organocatalysts
  作者：Marco Lombardo、Elisa Montroni、Arianna Quintavalla、Claudio Trombini

  DOI：10.1002/adsc.201200922

  日期：2012.12.14

  family of bicyclic silyl ether organocatalysts that display some remarkable features. Apart from being extremely stable to hydrolytic conditions and possessing excellent catalytic performances, the rigidity of the bicyclic structure imposes a synclinal endo disposition of the bulky substituents with respect to the pyrrolidine ring, opposed to the more stable synclinal exo conformations of Jørgensen–Hayashi

  反式-4-L-羟基脯氨酸的简单化学操作即可获得具有某些显着特征的新的双环甲硅烷基醚有机催化剂家族。除了在水解条件下极其稳定并具有出色的催化性能外，双环结构的刚性还使大取代基相对于吡咯烷环具有向斜内的位置，这与Jørgensen-Hayashi催化剂的向斜外型构象相反。
• Digitization and validation of a chemical synthesis literature database in the ChemPU
  作者：Simon Rohrbach、Mindaugas Šiaučiulis、Greig Chisholm、Petrisor-Alin Pirvan、Michael Saleeb、S. Hessam M. Mehr、Ekaterina Trushina、Artem I. Leonov、Graham Keenan、Aamir Khan、Alexander Hammer、Leroy Cronin

  DOI：10.1126/science.abo0058

  日期：2022.7.8

  Despite huge potential, automation of synthetic chemistry has only made incremental progress over the past few decades. We present an automatically executable chemical reaction database of 100 molecules representative of the range of reactions found in contemporary organic synthesis. These reactions include transition metal–catalyzed coupling reactions, heterocycle formations, functional group interconversions, and multicomponent reactions. The chemical reaction codes or χDLs for the reactions have been stored in a database for version control, validation, collaboration, and data mining. Of these syntheses, more than 50 entries from the database have been downloaded and robotically run in seven modular ChemPU’s with yields and purities comparable to those achieved by an expert chemist. We also demonstrate the automatic purification of a range of compounds using a chromatography module seamlessly coupled to the platform and programmed with the same language.

  尽管潜力巨大，但合成化学的自动化在过去几十年中仅取得了循序渐进的进展。我们介绍了一个可自动执行的化学反应数据库，其中包含 100 个分子，代表了当代有机合成中的各种反应。这些反应包括过渡金属催化的偶联反应、杂环形成、官能团相互转化和多组分反应。这些反应的化学反应代码或 χDLs 已存储在数据库中，用于版本控制、验证、协作和数据挖掘。在这些合成中，我们从数据库中下载了 50 多个条目，并在 7 个模块化 ChemPU 中以机器人方式运行，其产率和纯度可与专家化学家的水平相媲美。我们还演示了使用与平台无缝耦合并使用相同语言编程的色谱模块自动纯化一系列化合物。
• Studies on Hydroxyproline
  作者：Arthur A. Patchett、Bernhard Witkop

  DOI：10.1021/ja01558a050

  日期：1957.1
• New chiral proline-based catalysts for silicon and zirconium oxides-promoted asymmetric Biginelli reaction
  作者：Yulia A. Titova、Dmitry A. Gruzdev、Olga V. Fedorova、Olga A. Alisienok、Anna N. Murashkevich、Victor P. Krasnov、Gennady L. Rusinov、Valery N. Charushin

  DOI：10.1007/s10593-018-2285-z

  日期：2018.4

  4-Hydroxy-(2S)-prolines bearing 3,4-dihydro-2H-1,4-benzoxazine or 1,2,3,4-tetrahydroquinoline fragments were synthesized and studied as chiral catalysts in the Biginelli reaction. The target product ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate was obtained with 54% enantiomeric excess (ee). An increase in ee values of the reaction product up to 76% was observed in the presence of nanosized oxides SiO2-ZrO2 as heterogeneous promoters.
• Bowers-Nemia, Margaret M.; Joullie, Madeleine M., Heterocycles, 1983, vol. 20, # 5, p. 817 - 828
  作者：Bowers-Nemia, Margaret M.、Joullie, Madeleine M.

  DOI：——

  日期：——