2-cyano-2-methylpiperidine-1-carboxylic acid tert-butyl ester | 746658-72-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-cyano-2-methylpiperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 2-methyl-2-cyanopiperidine-1-carboxylate；tert-Butyl 2-cyano-2-methylpiperidine-1-carboxylate
• CAS: 746658-72-0
• 化学式: C₁₂H₂₀N₂O₂
• 分子量: 224.303
• InChiKey: GFJGITBGEUGJIU-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  327.9±35.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cyano-2-methylpiperidine-1-carboxylic acid tert-butyl ester 在 正丁基锂 、 1,10-菲罗啉 、 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium 、 氘代甲醇 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 15.0h， 以91%的产率得到
  参考文献：
  名称：

  叔α-氨基有机锂试剂的产生和实用性。

  摘要：

  已经开发了通过α-氨基腈的还原锂化来制备叔α-氨基有机锂试剂的一般方法。这类有机锂亲核试剂可与羰基亲电试剂有效反应，或在分子内环化中与束缚的磷酸酯离去基团有效反应。可以使用重金属化来生产与烷基卤化物亲电试剂反应并与烯酮进行1,4-加成反应的α-氨基有机酸试剂。这些方法建立了一种新的合成氮原子附近的季中心的方法。[反应：看文字]

  DOI：

  10.1021/ol049039p
• 作为产物：
  描述：

  1-Boc-2-氰基哌啶 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.17h， 生成 2-cyano-2-methylpiperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Arylthio-Metal Exchange of α-Arylthioalkanenitriles

  摘要：

  The addition of BuLi, Bu3MgLi, Et2ZnBuLi, or Me2CuLi to alpha-arylthioalkanenitriles triggers an arylthio-metal exchange. NMR spectroscopic analyses implicate organometallic attack on sulfur forming a three-coordinate sulfidate as the key intermediate. Electrophilic trapping affords tertiary and quaternary nitriles in high yield. The method addresses the challenge of improving the functional group tolerance and preventing polyalkylations.

  DOI：

  10.1021/ol403020s

文献信息

• Dihydroxy-pyrimidine and N-methylpyrimidone HIV-integrase inhibitors: Improving cell based activity by the quaternarization of a chiral center
  作者：Emanuela Nizi、Maria Vittoria Orsale、Benedetta Crescenzi、Giovanna Pescatore、Ester Muraglia、Anna Alfieri、Cristina Gardelli、Stéphane A.H. Spieser、Vincenzo Summa

  DOI：10.1016/j.bmcl.2009.06.091

  日期：2009.8

  In the context of HIV-integrase, dihydroxypyrimidine and N-methyl pyrimidone inhibitors the cellular activity of this class of compounds has been optimized by the introduction of a simple methyl substituent in the alpha-position of the C-2 side chains. Enhanced passive membrane permeability has been identified as the key factor driving the observed cell-based activity improvement. The rat PK profile of the alpha-methyl derivative 26a was also improved over its des-methyl exact analog. (C) 2009 Elsevier Ltd. All rights reserved.
• Arylthio-Metal Exchange of α-Arylthioalkanenitriles
  作者：Dinesh Nath、Melanie C. Skilbeck、Iain Coldham、Fraser F. Fleming

  DOI：10.1021/ol403020s

  日期：2014.1.3

  The addition of BuLi, Bu3MgLi, Et2ZnBuLi, or Me2CuLi to alpha-arylthioalkanenitriles triggers an arylthio-metal exchange. NMR spectroscopic analyses implicate organometallic attack on sulfur forming a three-coordinate sulfidate as the key intermediate. Electrophilic trapping affords tertiary and quaternary nitriles in high yield. The method addresses the challenge of improving the functional group tolerance and preventing polyalkylations.
• Generation and Utility of Tertiary α-Aminoorganolithium Reagents
  作者：Scott A. Wolckenhauer、Scott D. Rychnovsky

  DOI：10.1021/ol049039p

  日期：2004.8.1

  approach to tertiary alpha-aminoorganolithium reagents by reductive lithiation of alpha-aminonitriles has been developed. This class of organolithium nucleophiles reacts efficiently with carbonyl electrophiles or in intramolecular cyclizations with tethered phosphate leaving groups. Transmetalation can be used to produce alpha-aminoorganocuprate reagents that react with alkyl halide electrophiles and

  已经开发了通过α-氨基腈的还原锂化来制备叔α-氨基有机锂试剂的一般方法。这类有机锂亲核试剂可与羰基亲电试剂有效反应，或在分子内环化中与束缚的磷酸酯离去基团有效反应。可以使用重金属化来生产与烷基卤化物亲电试剂反应并与烯酮进行1,4-加成反应的α-氨基有机酸试剂。这些方法建立了一种新的合成氮原子附近的季中心的方法。[反应：看文字]