benzyl 2-methylpyrrolidine-1-carboxylate

• 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: benzyl 2-methylpyrrolidine-1-carboxylate
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: QRXDMGQDNTUTTO-UHFFFAOYSA-N

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

• 作为产物：
  描述：

  4-戊烯-1-醇 在 magnesium sulfate silver tetrafluoroborate 、 偶氮二甲酸二异丙酯 、 2,6-bis(diphenylphosphinomethyl)pyridine dichloropalladium 、 copper(II) bis(trifluoromethanesulfonate) 、 一水合肼 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 0.25h， 生成 benzyl 2-methylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  未活化烯烃的室温钯催化分子内加氢胺化

  摘要：

  描述了一种温和且简便的 Pd 催化的未活化烯烃的分子内加氢胺化。该反应在室温下发生并且可以耐受合成有用的酸敏感官能团。加氢胺化产物而不是氧化胺化产物的形成是由于在 Pd 上使用了三齿配体，它有效地抑制了 β-氢化物的消除。

  DOI：

  10.1021/ja060126h

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。
• 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）。
• Nickel Catalysis via S_H2 Homolytic Substitution: The Double Decarboxylative Cross-Coupling of Aliphatic Acids
  作者：Artem V. Tsymbal、Lorenzo Delarue Bizzini、David W. C. MacMillan

  DOI：10.1021/jacs.2c08989

  日期：2022.11.23

  generation, radical sorting via selective binding to a Ni(II) center, and bimolecular homolytic substitution (SH2) at a high-valent nickel–alkyl complex. This catalytic manifold enables the hitherto elusive cross-coupling of diverse aliphatic carboxylic acids to generate valuable C(sp3)–C(sp3)-products. Notably, the powerful SH2 mechanism provides general access to sterically encumbered quaternary carbon

  交叉偶联平台传统上是围绕一系列闭壳步骤构建的，例如氧化加成、金属转移和还原消除。在此，我们描述了一种双光/镍催化歧管，它通过互补序列进行交叉偶联，涉及自由基生成、通过选择性结合到 Ni(II) 中心的自由基分选以及高催化下的双分子均解取代 (S H 2)。 -价镍-烷基络合物。这种催化歧管能够实现迄今为止难以捉摸的不同脂肪族羧酸的交叉偶联，生成有价值的 C(sp 3 )–C(sp 3 )-产物。值得注意的是，强大的 S H 2 机制提供了对空间阻碍的季碳中心的普遍访问，解决了片段偶联化学中长期存在的挑战。
• PROCESSES FOR PRODUCING OPTICALLY ACTIVE 1-SUBSTITUTED 2-METHYLPYRROLIDINE AND INTERMEDIATE THEREFOR
  申请人：KANEKA CORPORATION

  公开号：EP1715054A1

  公开（公告）日：2006-10-25

  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.

  本发明涉及一种通过不对称还原5-羟基-2-戊酮生产光学活性1,4-戊二醇的工艺，该工艺成本低，易于获得。本发明还涉及一种生产光学活性 1-取代 2-甲基吡咯烷的工艺，包括对光学活性 1,4-戊二醇进行磺化以将其转化为光学活性磺酸盐化合物，并使该化合物与胺反应。根据本发明的工艺，光学活性的 1,4-戊二醇和光学活性的 1-取代 2-甲基吡咯烷可以简单地从廉价的起始原料中生产出来，这两种物质可用作医药中间体和农药中间体。