N-(3-methyl-2-butenyl)pyridin-2-amine | 62327-66-6

• 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: N-(3-methyl-2-butenyl)pyridin-2-amine
• 英文别名: N-(3-methylbut-2-enyl)pyridin-2-amine；N-(3-Methylbut-2-en-1-yl)pyridin-2-amine
• CAS: 62327-66-6
• 化学式: C₁₀H₁₄N₂
• 分子量: 162.235
• InChiKey: YJJRIKKGZXGQHB-UHFFFAOYSA-N

物化性质

• 沸点：
  272.7±15.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-methyl-2-butenyl)pyridin-2-amine 、 富马酸 以 丙酮 为溶剂， 反应 0.17h， 生成 N-(3-methylbut-2-enyl)pyridin-2-amine fumarate
  参考文献：
  名称：

  Benzylguanidines and Other Galegine Analogues Inducing Weight Loss in Mice

  摘要：

  Dimethylallylguanidine, also known as galegine, isolated from Galega officinalis, has been shown to have weight reducing properties in vivo. Substitution of the guanidine group with an N-cyano group and replacement of guanidine with amidine, pyrimidine, pyridine, or the imidazole moieties removed the weight reducing properties when evaluated in BALB/c mice. However, retention of the guanidine and replacement of the dimethylallyl group by a series of functionalized benzyl substituents was shown to exhibit, and in some cases significantly improve, the weight reducing properties of these molecules in BALB/c, ob/ob, and diet induced obesity (DIO) mice models. The lead compound identified, across all models, was 1-(4-chlorobenzyl)guanidine hemisulfate, which gave an average daily weight difference (% from time-matched controls; +/- SEM) of -19.7 +/- 1.0, -11.0 +/- 0.7, and -7.3 +/- 0.8 in BALB/c, ob/ob, and DIO models, respectively.

  DOI：

  10.1021/jm8011933
• 作为产物：
  描述：

  2-氨基吡啶 、 2-甲基-3-丁烯-2-醇 在 正丁基锂 、 四氯化钛 、 二乙胺 、 碘代三甲硅烷 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以38%的产率得到N-(3-methyl-2-butenyl)pyridin-2-amine
  参考文献：
  名称：

  经计算设计的钛介导的烯丙醇胺化反应，用于合成仲烯丙胺†

  摘要：

  以前的机理研究启发了计算设计，并且在仲烯丙胺的合成中实施了DFT指导的反应。钛亚氨基中间体的参与促进了反应，并且在键形成步骤中的闭合过渡态提供了唯一的S N 2'取代产物。

  DOI：

  10.1039/c5ra18503c

文献信息

• 一种烯丙胺合成方法
  申请人：南开大学

  公开号：CN105315116B

  公开（公告）日：2018-01-30

  本发明提供了以取代烯丙醇和芳香胺类为原料，通过钛金属中间体的介导制备烯丙胺类化合物的合成方法。本发明涉及烯丙基取代的二级胺，具体为N‑芳基‑N‑烯丙基胺，它们具有如下的化学结构通式：其中：R1，R2，R3，R4为氢，烷基或苯基；Ar为苯基，4‑卤代苯基，2‑卤代苯基或2‑吡啶基。本发明公开了这些化合物的化学结构以及合成方法。
• Benzylguanidines and Other Galegine Analogues Inducing Weight Loss in Mice
  作者：Geoffrey D. Coxon、Brian L. Furman、Alan L. Harvey、John McTavish、Mark H. Mooney、Mahmoud Arastoo、Alan R. Kennedy、Justice M. Tettey、Roger D. Waigh

  DOI：10.1021/jm8011933

  日期：2009.6.11

  Dimethylallylguanidine, also known as galegine, isolated from Galega officinalis, has been shown to have weight reducing properties in vivo. Substitution of the guanidine group with an N-cyano group and replacement of guanidine with amidine, pyrimidine, pyridine, or the imidazole moieties removed the weight reducing properties when evaluated in BALB/c mice. However, retention of the guanidine and replacement of the dimethylallyl group by a series of functionalized benzyl substituents was shown to exhibit, and in some cases significantly improve, the weight reducing properties of these molecules in BALB/c, ob/ob, and diet induced obesity (DIO) mice models. The lead compound identified, across all models, was 1-(4-chlorobenzyl)guanidine hemisulfate, which gave an average daily weight difference (% from time-matched controls; +/- SEM) of -19.7 +/- 1.0, -11.0 +/- 0.7, and -7.3 +/- 0.8 in BALB/c, ob/ob, and DIO models, respectively.
• A computationally designed titanium-mediated amination of allylic alcohols for the synthesis of secondary allylamines
  作者：Zunming Sun、Qingxia Wang、Yi Xu、Zhihong Wang

  DOI：10.1039/c5ra18503c

  日期：——

  A computational design was inspired by previous mechanistic studies and the DFT-guided reactions were implemented in the synthesis of secondary allylamines. The participation of titanium imido intermediates facilitated the reaction and the closed transition states in the bond-forming steps rendered exclusive SN2′ substitution products.

  以前的机理研究启发了计算设计，并且在仲烯丙胺的合成中实施了DFT指导的反应。钛亚氨基中间体的参与促进了反应，并且在键形成步骤中的闭合过渡态提供了唯一的S N 2'取代产物。