(R)-2-methyl-1-pyrrolidinecarboxylic acid phenylmethyl ester | 117607-12-2

• 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: (R)-2-methyl-1-pyrrolidinecarboxylic acid phenylmethyl ester
• 英文别名: benzyl (S)-2-methylpyrrolidine-1-carboxylate；benzyl 2-methylpyrrolidine-1-carboxylate；(R)-2-Methyl-1-pyrrolidinecarboxylic acid benzyl ester；benzyl (2R)-2-methylpyrrolidine-1-carboxylate
• CAS: 117607-12-2
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: QRXDMGQDNTUTTO-LLVKDONJSA-N

物化性质

• 密度：
  1.107

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (R)-2-methyl-1-pyrrolidinecarboxylic acid phenylmethyl ester 在 氢溴酸 、 溶剂黄146 作用下， 以96%的产率得到(R)-2-methylpyrrolidine hydrobromide
  参考文献：
  名称：

  A new class of potent non-imidazole H3 antagonists: 2-aminoethylbenzofurans

  摘要：

  2-Aminoethylbenzofurans constitute a new class of H-3 antagonists that are more rotationally constrained than most previously reported H-3 antagonists. They retain high potency at human and rat receptors, with efficient CNS penetration observed in 35. The SAR of the basic amine moiety was compared in three different series of analogues. The greatest potency was found in analogues bearing a 2-methylpyrrolidine, a 2,5-dimethylpyrrolidine, or a 2,6-dimethylpiperidine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.032
• 作为产物：
  描述：

  (S)-1-n-cbz-2-氯甲基吡咯烷 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以85%的产率得到(R)-2-methyl-1-pyrrolidinecarboxylic acid phenylmethyl ester
  参考文献：
  名称：

  A new class of potent non-imidazole H3 antagonists: 2-aminoethylbenzofurans

  摘要：

  2-Aminoethylbenzofurans constitute a new class of H-3 antagonists that are more rotationally constrained than most previously reported H-3 antagonists. They retain high potency at human and rat receptors, with efficient CNS penetration observed in 35. The SAR of the basic amine moiety was compared in three different series of analogues. The greatest potency was found in analogues bearing a 2-methylpyrrolidine, a 2,5-dimethylpyrrolidine, or a 2,6-dimethylpiperidine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.032

文献信息

• Catalytic Reduction of Alkyl and Aryl Bromides Using Propan-2-ol
  作者：Michael C. Haibach、Brian M. Stoltz、Robert H. Grubbs

  DOI：10.1002/anie.201708800

  日期：2017.11.20

  complex: Milstein's complex, (PNN)RuHCl(CO), catalyzes the efficient reduction of alkyl bromides and chlorides under relatively mild reaction conditions by using propan-2-ol and a base. Sterically hindered tertiary and neopentyl substrates are reduced efficiently, as well as more-functionalized aryl and alkyl bromides. The reaction appears to occur by a radical pathway, and provides an alternative to

  一个简单的配合物：米尔斯坦配合物（PNN）RuHCl（CO），通过使用丙-2-醇和一种碱，在相对温和的反应条件下催化有效还原烷基溴化物和氯化物。受阻位的叔和新戊基底物以及功能更强的芳基和烷基溴化物均能有效还原。该反应似乎是通过自由基途径发生的，它提供了硅烷，氢化锂铝和锡基还原的替代方法。
• Processes for Producing Optically Active 1-Substituted 2-Methylpyrrolidine and Intermediate Therefor
  申请人：Nishiyama Akira

  公开号：US20070292926A1

  公开（公告）日：2007-12-20

  The present invention relates to a process for producing an optically active 1,4-pentanediol by asymmetrically reducing 5-hydroxy-2-pentanone, which is easily available at low cost. The present invention also relates to a process for producing an optically active 1-substituted 2-methylpyrrolidine including sulfonylating the optically active 1,4-pentanediol to convert it to an optically active sulfonate compound, and reacting the compound with an amine. According to the processes of the present invention, an optically active 1,4-pentanediol and an optically active 1-substituted 2-methylpyrrolidine, which are useful as an intermediate for medicines and an intermediate for agricultural chemicals, can be simply produced from an inexpensive starting material.

  本发明涉及一种生产光学活性1,4-戊二醇的过程，该过程通过非对称还原低成本易得的5-羟基-2-戊酮。本发明还涉及一种生产光学活性1-取代-2-甲基吡咯烷的过程，包括将光学活性1,4-戊二醇磺酰化以转化为光学活性磺酸盐化合物，并将该化合物与胺反应。根据本发明的工艺，可以从廉价的起始材料简单地生产出作为药物中间体和农药中间体的光学活性1,4-戊二醇和光学活性1-取代-2-甲基吡咯烷。
• Acylative kinetic resolution of racemic methyl-substituted cyclic alkylamines with 2,5-dioxopyrrolidin-1-yl (<i>R</i>)-2-phenoxypropanoate
  作者：Dmitry A. Gruzdev、Sergey A. Vakarov、Marina A. Korolyova、Ekaterina V. Bartashevich、Andrey A. Tumashov、Evgeny N. Chulakov、Marina A. Ezhikova、Mikhail I. Kodess、Galina L. Levit、Victor P. Krasnov

  DOI：10.1039/d1ob02099d

  日期：——

  methyl-substituted cyclic alkylamines with active esters of 2-phenoxypropanoic acid was studied in detail. The ester of (R)-2-phenoxypropanoic acid and N-hydroxysuccinimide was found to be the most selective agent. The highest stereoselectivity was observed in the kinetic resolution of racemic 2-methylpiperidine in toluene at −40 °C (selectivity factor s = 73) with the predominant formation of (R,R)-amide

  详细研究了一些外消旋甲基取代的环状烷基胺与2-苯氧基丙酸的活性酯的非对映选择性酰化反应。( R )-2-苯氧基丙酸和N-羟基琥珀酰亚胺的酯被发现是最具选择性的试剂。在 -40 °C 下，在甲苯中的外消旋 2-甲基哌啶的动力学拆分中观察到最高的立体选择性（选择性因子s = 73），主要形成 ( R , R )-酰胺 (93.7% de）。为了解释观察到的立体选择性，对标题酰化剂与 2-甲基哌啶和 2-甲基吡咯烷反应中的过渡态进行了 DFT 建模。计算值与实验数据吻合良好。已经证明酰化通过协同机制进行，其中胺的添加与羟基琥珀酰亚胺片段的消除同时发生。与 ( R , S )-酰胺的形成相比，( R , R )-酰胺形成的高立体选择性很大程度上是由过渡态中较低的空间位阻确保的。
• Asymmetric Intramolecular Hydroamination of Alkenes in Mild and Wet Conditions-Structure and Reactivity of Cationic Binuclear Gold(I) Catalysts
  作者：Marc-Antoine Abadie、Xavier Trivelli、Florian Medina、Frédéric Capet、Pascal Roussel、Francine Agbossou-Niedercorn、Christophe Michon

  DOI：10.1002/cctc.201402350

  日期：2014.8

  binuclear gold(I) chloride complex was combined with a silver salt to catalyze efficiently, for the first time, the asymmetric intramolecular hydroamination of alkenes with high conversions and enantioselectivities, in mild conditions and in presence of water. Both enantiomers of the products could be obtained by controlling the molecular ion‐pairs through the solvent polarity. The gold(I) cationic

  将所选的二膦双核氯化金（I）络合物与银盐混合，以在温和的条件下和在水的存在下，首次有效地催化具有高转化率和对映选择性的烯烃的不对称分子内加氢胺化反应。可以通过通过溶剂极性控制分子离子对来获得产物的两种对映异构体。通过X射线分析和溶液中的DOSY 1 H NMR实验，清楚地表征了金（I）阳离子活性物质的固态。在催化剂的结合方式上未观察到氯化银的贡献。
• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE AMINE DERIVATIVE
  申请人：Nagasawa Toru

  公开号：US20110262977A1

  公开（公告）日：2011-10-27

  Optically active amine derivatives are produced by acting on imine derivatives with a culture of microorganisms having the ability to stereoselectively reduce the compounds, microbial cells, or processed products thereof, followed by collecting the generated optically active amine derivatives. Optically active amine derivatives obtained in the present invention are useful as materials for pharmaceutical agents. The present invention enables, for example, production of an optically active compound represented by formula (IV): (wherein R group represents an alkyl group having one to three carbon atoms; and n represents an integer of 1 to 4).

  光学活性胺衍生物是通过用具有立体选择性还原化合物的微生物培养物作用于亚胺衍生物，微生物细胞或其加工产品，然后收集生成的光学活性胺衍生物而制备的。本发明所得到的光学活性胺衍生物可用作制药剂的材料。例如，本发明使得可以生产由公式（IV）表示的光学活性化合物：（其中R基表示具有1至3个碳原子的烷基基团；n表示1至4的整数）。