6-tert-butylnicotine | 83218-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-tert-butylnicotine
• 英文别名: 2-(tert-butyl)-5-(1-methylpyrrolidin-2-yl)pyridine；2-Tert-butyl-5-(1-methylpyrrolidin-2-yl)pyridine
• CAS: 83218-45-5
• 化学式: C₁₄H₂₂N₂
• 分子量: 218.342
• InChiKey: UOMNQBXGERVLKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  S-tert-butyl O-ethyl carbonodithioate 、 (+/-)-尼古丁 在 过氧化双月桂酰 、 camphor-10-sulfonic acid 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以83%的产率得到6-tert-butylnicotine
  参考文献：
  名称：

  Xanthate-Mediated Incorporation of Quaternary Centers into Heteroarenes

  摘要：

  The xanthate-mediated addition of tertiary alkyl radicals to heteroarenes enabled the easy functionalization of heteroaromatic rings as well as more decorated structures, such as marketed drugs or agrochemicals. This work provides a synthetic tool for efficiently exploring the chemical space by allowing late-stage diversification with a high tolerance toward functional groups.

  DOI：

  10.1021/acs.orglett.8b01299

文献信息

• Nicotine chemistry
  作者：Jeffrey I. Seeman、Charles G. Chavdarian、Richard A. Kornfeld、John D. Naworal

  DOI：10.1016/s0040-4020(01)96505-6

  日期：1985.1

  Organolithium reagents (RLi; where R = ethyl, isopropyl,cyclopropyl,n-butyl, sec-butyl, t-butyl, vinyl) have been found to add regiospecifically to (—)-nicotine to provide a series of 6-substituted nicotinoids of low optical activity. The data presented for the organolithium additions coupled with an analysis of the addition oft-BuLi to(—)-nicotine and [2'-2H]nicotine have provided strong evidence

  已发现有机锂试剂（RLi；其中R =乙基，异丙基，环丙基，正丁基，仲丁基，叔丁基，乙烯基）会向（-）-烟碱区域特异性地添加，从而提供一系列的6-取代烟碱低光学活性。所提供的有关有机锂添加的数据以及对（-）-烟碱和[2'- 2 H]烟碱的t-BuLi的添加的分析，为吡咯烷环开环和涉及的重合引起的新型消旋过程提供了有力的证据。尼古丁的N'-C” 2键。
• The -butylation of nicotine: novel reaction pathways and racemization studies
  作者：Charles G. Chavdarian、Jeffrey I. Seeman

  DOI：10.1016/s0040-4039(00)87384-0

  日期：1982.1

  The reaction of nicotine with -butyllithium gives 6--butylnicotine () and two novel pyrrolidine ring cleaved products, and ; mechanisms for the racemization of , , and were elucidated by reacting -butyllithium with nicotine-2′-d1.

  与尼古丁的反应丁基锂给出6- -butylnicotine（ ）和两个新的吡咯烷环裂解产品，和; 对的外消旋化的机制，以及通过反应阐明丁基锂与尼古丁-2'- d 1。
• QUINUCLIDINE COMPOUNDS AS ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS
  申请人：Cook, II James H.

  公开号：US20090270405A1

  公开（公告）日：2009-10-29

  The disclosure provides compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds are ligands for the nicotinic α7 receptor and may be useful for the treatment of various disorders of the central nervous system, especially affective and neurodegenerative disorders.

  该披露提供了公式I的化合物，包括它们的盐，以及使用这些化合物的组合物和方法。这些化合物是烟碱性α7受体的配体，可能对治疗中枢神经系统的各种疾病，特别是情感和神经退行性疾病，有用。
• Quinuclidine Compounds as Alpha-7 Nicotinic Acetylcholine Receptor Ligands
  申请人：Cook, II James H.

  公开号：US20100099684A1

  公开（公告）日：2010-04-22

  The disclosure provides compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds are ligands for the nicotinic α7 receptor and may be useful for the treatment of various disorders of the central nervous system, especially affective and neurodegenerative disorders.

  本公开提供公式I的化合物，包括其盐，以及使用这些化合物的组合物和方法。这些化合物是尼古丁α7受体的配体，可能对中枢神经系统的各种疾病，特别是情感和神经退行性疾病的治疗有用。
• US7863291B2
  申请人：——

  公开号：US7863291B2

  公开（公告）日：2011-01-04