2-吡咯啉-1-乙酸苄酯 | 68471-56-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 中文名称: 2-吡咯啉-1-乙酸苄酯
• 中文别名: 乙基2,3-二氢吡咯-1-羧酸酯
• 英文名称: ethyl 2,3-dihydro-1H-pyrrole-1-carboxylate
• 英文别名: N-ethoxycarbonyl-2,3-dihydropyrrole；N-(Ethoxycarbonyl)-2-pyrroline；1-ethoxycarbonyl-2-pyrroline；ethyl 2,3-dihydropyrrole-1-carboxylate
• CAS: 68471-56-7
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: PWRMCZSQYLIXJC-UHFFFAOYSA-N

物化性质

• 沸点：
  210.6±23.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-吡咯啉-1-乙酸苄酯 在 tris-(dibenzylideneacetone)dipalladium(0) sodium acetate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (1S,2S,5R)-2-(4-Methoxy-phenyl)-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of dihydroxylated prolines and iminocyclitols from five-membered endocyclic enecarbamates. Total synthesis of the potent glycosidase inhibitor (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP)

  摘要：

  cis- and trans-3,4-Dihydroxylated prolines and the iminocyclitol 1,4-dideoxy-1,4-imino ribitol were synthesized employing a strategy involving the Heck arylation of five-membered endocyclic enecarbarnates with aryldiazonium salts followed by oxidative cleavage of the electron-rich aromatic ring. The total synthesis of the potent alpha- and beta-glucosidase inhibitor (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) was also achieved by the same strategy in ten steps from a chiral five-membered enecarbamate in 12% overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00017-0
• 作为产物：
  描述：

  ethyl 2-hydroxypyrrolidine-1-carboxylate 以 甲苯 为溶剂， 反应 36.0h， 生成 2-吡咯啉-1-乙酸苄酯
  参考文献：
  名称：

  Extensive substrate profiling of cyclopentadecanone monooxygenase as Baeyer–Villiger biocatalyst reveals novel regiodivergent oxidations

  摘要：

  Cyclopentadecanone monooxygenase (CPDMO) is one of the latest additions to the established library of Baeyer-Villiger monooxygenases. Desymmetrizations of substituted cyclobutanones and -hexanones as well as kinetic resolutions of racemic cycloketones are efficiently catalyzed by CPDMO. Moreover the enzyme shows unprecedented preference in regiodivergent oxidations of terpenones and the bicyclic Geissman-Waiss lactone precursor giving access to the optical antipode of retronecine and other pyrrolizidine alkaloids. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.07.003

文献信息

• Synthesis of new aza-bicyclic 2-isoxazolines by 1,3-dipolar cycloaddition of endocyclic enecarbamates and enamides with nitrile oxides
  作者：Valderes Moraes de Almeida、Rosiel José dos Santos、Alexandre José da Silva Góes、José Gildo de Lima、Carlos Roque Duarte Correia、Antônio Rodolfo de Faria

  DOI：10.1016/j.tetlet.2008.11.096

  日期：2009.2

  4-b]pyrrolidines, and 4,5-dihydroisoxazole[5,4-b]piperidines were synthesized in a highly regioselective manner through a 1,3-dipolar cycloaddition reaction of 5- and 6-membered endocyclic enecarbamates and enamides with several nitrile oxides in good to excellent yields. Hydrogenolysis of 5- and 6-membered Cbz-cycloadducts led to secondary amines, which presented distinctive stabilities. 2-Isoxazoline

  新型的氮杂双环2-异恶唑啉，4,5-二氢异恶唑[5,4- b ]吡咯烷和4,5-二氢异恶唑[5,4- b ]哌啶以高度区域选择性的方式通过1,3-偶极合成5元和6元环内氨基甲酸酯和酰胺与几种腈氧化物的环加成反应，收率良好或优异。5元和6元Cbz-环加合物的氢解反应生成仲胺，具有独特的稳定性。通过N-苯甲酰化，然后仲胺的氨解，或直接从环加合物的氨解，以高收率获得了2-异恶唑啉双酰胺。
• Highly active catalysts of bisphosphine oxides for asymmetric Heck reaction
  作者：Jian Hu、Yunpeng Lu、Yongxin Li、Jianrong (Steve) Zhou

  DOI：10.1039/c3cc45233f

  日期：——

  Bisphosphine oxides formed highly active asymmetric Heck catalysts, which were applied in asymmetric synthesis of pharmacologically active azacycles. Olefin insertion proceeded via cis pathways, different from P,N-ligands.

  双膦氧化物形成高活性的不对称Heck催化剂，可用于药理活性氮杂环化合物的不对称合成。不同于P，N-配体，通过顺式途径进行烯烃插入。
• [2+2] Cycloaddition reaction of cyclic enecarbamates and enamides with ketenes. A short and efficient synthesis of the Geissman-Waiss lactone.
  作者：Antônio R. de Faria、Carlos Roberto R. Matos、Carlos Roque D. Correia

  DOI：10.1016/s0040-4039(00)60049-7

  日期：1993.1

  The synthesis of several 2-aza-bicyclo[3.2.0] heptan-6-ones has been achieved in a regiospecific manner through a [2+2] cycloaddition reaction between

  通过[2 + 2]环加成反应之间的区域专一性，已经实现了几种2-氮杂-双环[3.2.0]庚烷-6-酮的合成。
• Catalytic asymmetric arylation of N-substituted 2-pyrrolines with aryl triflates
  作者：Fumiyuki Ozawa、Tamio Hayashi

  DOI：10.1016/0022-328x(92)83236-b

  日期：1992.4

  Catalytic asymmetric arylation of 1-(alkoxycarbonyl-2-pyrrolines (4) with aryl triflates (1) in benzene in the presence of a base and a palladium catalyst, prepared in situ by mixing Pd(OAc)2 and (R)-BINAP, gives optically active (R-1-(alkoxycarbonyl-5-aryl-2-pyrrolines (5) of up to 83% ee, together with the regioisomers 1-(alkoxycarbonyl)-5-aryl-3-pyrrolines (6).

  在碱和钯催化剂的存在下，通过混合Pd（OAc）2和（R）-BINAP原位制备的1-（烷氧基羰基-2-吡咯啉（4）与芳基三氟甲磺酸酯（1）在苯中的催化不对称芳基化反应得到具有高达83％ee的旋光性的R -1-（烷氧基羰基-5-芳基-2-吡咯啉（5），以及区域异构体1-（烷氧基羰基）-5-芳基-3-吡咯啉（6）。
• An Enantioselective Approach to <scp>Heteroatom‐Containing</scp> Bicyclic Derivatives via <scp>Inverse‐Electron‐Demand</scp> Diels−Alder Reactions
  作者：Jun‐Xiong He、Xu‐Ge Si、Qi‐Tao Lu、Qian‐Wei Zhang、Quan Cai

  DOI：10.1002/cjoc.202200441

  日期：2023.1

  important pharmacophores and prevalent in bioactive natural products and drug molecules. Herein, we report a unified approach for the divergent synthesis of chiral heteroatom-containing bicyclic derivatives by lanthanide (III)-catalyzed asymmetric inverse-electron-demand Diels–Alder reactions of 2-pyrones. These reactions occur with various readily available dihydropyrroles and dihydrofurans as dienophiles

  手性含杂原子的双环支架是重要的药效团，普遍存在于具有生物活性的天然产物和药物分子中。在此，我们报告了一种通过镧系元素 (III) 催化的 2-吡喃酮的不对称逆电子需求 Diels-Alder 反应发散合成手性含杂原子双环衍生物的统一方法。这些反应发生在各种容易获得的二氢吡咯和二氢呋喃作为亲二烯体时，为密集官能化的顺式- 氢吲哚和顺式 - 氢苯并呋喃提供了一个步骤经济的合成平台，具有优异的产率和对映选择性。(–)-α-lycorane 和 (–)-lycorine 生物碱的简明合成证明了这种方法的合成效用。