2-((2S)-1-甲基吡咯烷-2-基)乙腈 | 67824-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 2-((2S)-1-甲基吡咯烷-2-基)乙腈
• 英文名称: (S)-(-)-1-methyl-2-(cyanomethyl)pyrrolidine
• 英文别名: 2-((2S)-1-methylpyrrolidin-2-yl)ethanenitrile；[(2S)-1-Methylpyrrolidin-2-yl]acetonitrile；2-[(2S)-1-methylpyrrolidin-2-yl]acetonitrile
• CAS: 67824-39-9
• 化学式: C₇H₁₂N₂
• 分子量: 124.186
• InChiKey: OVIXBUQHNFPUEP-ZETCQYMHSA-N

物化性质

• 沸点：
  213.3±13.0 °C(Predicted)
• 密度：
  0.949±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((2S)-1-甲基吡咯烷-2-基)乙腈 在 氢溴酸 、 lithium diisopropyl amide 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 生成 (S)-(-)-2-bromonicotine
  参考文献：
  名称：

  Synthesis of optically active nicotinoids

  摘要：

  DOI：

  10.1021/jo00345a034
• 作为产物：
  描述：

  N-甲基-L-脯氨醇 在 氯化亚砜 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 3.25h， 生成 2-((2S)-1-甲基吡咯烷-2-基)乙腈
  参考文献：
  名称：

  Late intermediates in the biosynthesis of cocaine: 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate and methyl ecgonine

  摘要：

  Methyl (RS)-[1,2-C-13(2),1-C-14]-4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate was synthesized from a mixture of sodium [1,2-C-13(2)]- and (1-C-14]acetate. This beta-keto ester was administered to intact Erythroxylum coca plants, resulting in the formation of labeled cocaine and methyl ecgonine. The presence of contiguous C-13 atoms in these alkaloids at C-2 and C-9 was established by C-13 NMR spectroscopy, and the presence of C-14 at C-9 was established by a chemical degradation. These results are consistent with our new hypothesis for the biosynthesis of cocaine, which involves the intermediacy of 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate (rather than 2-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate) in the formation of the tropane moiety of cocaine. Support for this biogenetic scheme was also obtained by a biomimetic synthesis of 2-carbomethoxy-3-tropinone by the oxidation of methyl 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate with mercuric acetate. The formation of labeled cocaine and methyl ecgonine in leaf cuttings of Erythroxylum coca was observed after incubation with. [9-C-14]-2-carbomethoxy-3-tropinone. The degree of incorporation of this precursor into cocaine was significantly increased by the concomitant administration of the N-acetylcysteamine thioester of benzoic acid, with a corresponding reduction in the degree of incorporation into methyl ecgonine.

  DOI：

  10.1021/ja00024a039

文献信息

• PROCESS FOR THE RESOLUTION OF (R,S)-NICOTINE
  申请人：Divi Murali Krishna Prasad

  公开号：US20120197022A1

  公开（公告）日：2012-08-02

  (R,S)-Nicotine was resolved through diastereomeric salt formation using dibenzoyl-d-tartaric acid and dibenzoyl-l-tartaric acid to obtain enantiomerically pure (S)-nicotine and (R)-nicotine.

  (R,S)-尼古丁通过使用二苯乙酰-d-酒石酸和二苯乙酰-l-酒石酸形成对映异构盐来分离，以获得对映纯的(S)-尼古丁和(R)-尼古丁。
• KRAS G12C INHIBITORS
  申请人：Mirati Therapeutics, Inc.

  公开号：US20190144444A1

  公开（公告）日：2019-05-16

  The present invention relates to compounds that inhibit KRas G12C. In particular, the present invention relates to compounds that irreversibly inhibit the activity of KRas G12C, pharmaceutical compositions comprising the compounds and methods of use therefor.

  本发明涉及抑制KRas G12C的化合物。特别地，本发明涉及不可逆抑制KRas G12C活性的化合物、包含这些化合物的药物组合物及其使用方法。
• 8-Bromocaffeine (8-BC): A New Versatile Reagent for Conversion of ­Aldoximes into Nitriles
  作者：Mohammad Soltani Rad、Somayeh Behrouz、Abdo-Reza Nekoei

  DOI：10.1055/s-0031-129036

  日期：2012.5

  A rapid and highly convenient synthesis of nitriles from the corresponding aldoximes using 8-bromocaffeine (8-BC) is described. In this protocol, aldoximes react with 8-BC in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and N,N-dimethylformamide (DMF) to furnish the corresponding nitriles under both microwave-assisted and/or conventional heating (reflux) conditions in short times and in

  描述了使用 8-溴咖啡因 (8-BC) 从相应的醛肟快速和高度方便地合成腈。在该协议中，醛肟在 1,8-二氮杂双环 [5.4.0] undec-7-ene (DBU) 和 N,N-二甲基甲酰胺 (DMF) 存在下与 8-BC 反应，在两种微波下提供相应的腈 -辅助和/或常规加热（回流）条件在短时间内和良好的产量。这种方法对于结构多样的醛肟非常有效，包括脂肪族、芳香族和杂芳香族肟。
• Novel benzothiazole compounds and methods of use thereof
  申请人：Whitten P. Jeffrey

  公开号：US20060063761A1

  公开（公告）日：2006-03-23

  The present invention relates to methods of preparing compounds having formula (1), (2), (5), and ((6A)-(6D)) comprising contacting the corresponding ester, an amine with formula NHR 1 R 2 , and a Lewis acid having formula ML n , wherein L is a halogen atom or an organic radical, n is 3-5, and M is a group III elemental atom, a group IV elemental atom, As, Sb, V or Fe, wherein A, B, V, X, Z, W, R 1 , R 2 , R 5 , Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , and Z 8 are substituents. Z 4 , Z 5 , Z 6 , Z 7 , and Z 8 are substituents.

  本发明涉及制备具有式（1）、（2）、（5）和（（6A）-（6D））的化合物的方法，包括接触相应的酯、具有式NHR1R2的胺和具有式MLn的Lewis酸，其中L是卤素原子或有机基团，n为3-5，M为III族元素原子、IV族元素原子、As、Sb、V或Fe，其中A、B、V、X、Z、W、R1、R2、R5、Z1、Z2、Z3、Z4、Z5、Z6、Z7和Z8为取代基。Z4、Z5、Z6、Z7和Z8为取代基。
• Process for the preparation of optically active nicotine analogs
  申请人：Philip Morris, Incorporated

  公开号：US04321387A1

  公开（公告）日：1982-03-23

  A method is disclosed for preparing chiral nicotine and nicotine analogues of the formula: ##STR1## wherein R.sub.1, R.sub.2, and R.sub.3 are hydrogen or alkyl and R.sub.4 is alkyl. Also disclosed are novel intermediate compounds and a novel method for preparing 1-methylprolinol from prolinol, which compounds and method are useful for the preparation of these nicotinoids.

  公开了一种制备手性尼古丁和尼古丁类似物的方法，其化学式为：##STR1## 其中R.sub.1、R.sub.2和R.sub.3为氢或烷基，R.sub.4为烷基。还公开了一些新颖的中间化合物和一种从脯氨醇制备1-甲基脯氨醇的新方法，这些化合物和方法对于制备这些烟碱类化合物是有用的。