1-(3-pyridyl)buten-3-ylamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(3-pyridyl)buten-3-ylamine
• 英文别名: 1-(pyridin-3-yl)but-3-en-1-amine；1-pyridin-3-ylbut-3-en-1-amine
• 化学式: C₉H₁₂N₂
• 分子量: 148.208
• InChiKey: RZGASQMKKMRHBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-pyridyl)buten-3-ylamine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 21.5h， 生成 (±)-毒藜碱
  参考文献：
  名称：

  From building block to natural products: a short synthesis and complete NMR spectroscopic characterization of (±)-anatabine and (±)-anabasine

  摘要：

  A short and straightforward synthesis of the racemic tobacco alkaloids anatabine and anabasine in five and six steps, respectively, from 3-pyridinecarboxaldehyde utilizing Barbier-type Zn-mediated allylation and ring-closing olefin metathesis, as the key steps, is reported. Additionally, a complete NMR spectroscopic analysis of the final products is carried out and full assignment of the NMR spectra of anatabine and anabasine with accurate coupling constants is accomplished and reported here for the first time. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.093
• 作为产物：
  描述：

  N,N-(dimethylsulfamoyl)-3-pyridinylaldimine 在 1,3-丙二胺 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 1-(3-pyridyl)buten-3-ylamine
  参考文献：
  名称：

  From building block to natural products: a short synthesis and complete NMR spectroscopic characterization of (±)-anatabine and (±)-anabasine

  摘要：

  A short and straightforward synthesis of the racemic tobacco alkaloids anatabine and anabasine in five and six steps, respectively, from 3-pyridinecarboxaldehyde utilizing Barbier-type Zn-mediated allylation and ring-closing olefin metathesis, as the key steps, is reported. Additionally, a complete NMR spectroscopic analysis of the final products is carried out and full assignment of the NMR spectra of anatabine and anabasine with accurate coupling constants is accomplished and reported here for the first time. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.093

文献信息

• α-Aminoallylation of aldehydes in aqueous ammonia
  作者：Shū Kobayashi、Keiichi Hirano、Masaharu Sugiura

  DOI：10.1039/b415264f

  日期：——

  α-Aminoallylation of aldehydes in aqueous ammonia has been developed; commercial aqueous ammonia was successfully used, and this method does not require anhydrous conditions thus leading to easy and practical operations.

  水合氨中醛的α-氨基烯丙基化方法已得到开发；成功使用了商用水合氨，该方法无需无水条件，从而简化了操作，更具实用价值。
• New Generation of Highly Reactive Allylborating Agents For Cu(I)-Catalyzed Allylation of Chiral Sulfinylimines
  作者：Michael S. Alexeev、Tatyana V. Strelkova、Michail M. Ilyin, Jr.、Yulia V. Nelyubina、Ivan A. Bespalov、Michael Medvedev、Victor N Khrustalev、Nikolai Kuznetsov

  DOI：10.1039/d4ob00291a

  日期：——

  active reagents is an attractive strategy that meets the modern principles of sustainable development of chemistry. In the current study, we for the first time describe the method and general principles of Cu(I)-catalyzed allylation of imines with amine adducts of allylic triorganoboranes. Triallylborane is an extremely reactive compound and cannot be used for the catalytic allylation of imines, whereas

  使用高活性试剂实施选择性催化过程是一种有吸引力的策略，符合化学可持续发展的现代原则。在本研究中，我们首次描述了Cu( I )催化亚胺与烯丙基三有机硼烷胺加合物的烯丙基化反应的方法和一般原理。三烯丙基硼烷是一种极其活泼的化合物，不能用于亚胺的催化烯丙基化，而其胺加合物是理想的催化底物。胺片段的结构成功地平衡了烯丙基硼试剂的安全性、选择性和稳定性，使其在催化烯丙基化反应中表现出高活性，超过任何已知的烯丙基硼烷许多倍。获得的结果得到定量动力学数据和 DFT 计算的支持。该系统的催化功效在亚磺酰亚胺模型（23 个例子）上得到了证明。实现了高达 >99% 的高非对映选择性，包​​括克级合成 2-羟基苯基衍生物。考虑到三烯基硼烷（AAT）的胺加合物的高反应活性和无与伦比的原子经济性，它们可以被认为是Cu（ I ）和其他合适金属催化剂的潜在烯丙基化试剂。
• Lipase catalysis in the preparation of 3-(1-amino-3-butenyl)pyridine enantiomers
  作者：Ari Hietanen、Tiina Saloranta、Reko Leino、Liisa T. Kanerva

  DOI：10.1016/j.tetasy.2012.09.003

  日期：2012.12

  The kinetic resolution of 1-(3-pyridyl)buten-3-ylamine with activated and non-activated acyl donors and Burkholderia cepacia lipase (lipase PS-D) under dry conditions has been studied. The N-acylation in isopropyl acetate (E > 100) and the acidic hydrolysis of the (R)-amide produced gave the corresponding enantiomerically enriched amines. (C) 2012 Elsevier Ltd. All rights reserved.
• Development of a 2-Aza-Cope-[3 + 2] Dipolar Cycloaddition Strategy for the Synthesis of Quaternary Proline Scaffolds
  作者：Michael P. McCormack、Tamila Shalumova、Joseph M. Tanski、Stephen P. Waters

  DOI：10.1021/ol101606v

  日期：2010.9.3

  A one-pot multicomponent procedure for the synthesis of highly functionalized pyrrolidine rings through a domino 2-aza-Cope-[3 + 2] dipolar cycloaddition sequence has been demonstrated. This protocol was found to be both high-yielding and stereoselective for the endo cycloadduct.
• From building block to natural products: a short synthesis and complete NMR spectroscopic characterization of (±)-anatabine and (±)-anabasine
  作者：Tiina Saloranta、Reko Leino

  DOI：10.1016/j.tetlet.2011.06.093

  日期：2011.9

  A short and straightforward synthesis of the racemic tobacco alkaloids anatabine and anabasine in five and six steps, respectively, from 3-pyridinecarboxaldehyde utilizing Barbier-type Zn-mediated allylation and ring-closing olefin metathesis, as the key steps, is reported. Additionally, a complete NMR spectroscopic analysis of the final products is carried out and full assignment of the NMR spectra of anatabine and anabasine with accurate coupling constants is accomplished and reported here for the first time. (C) 2011 Elsevier Ltd. All rights reserved.