(E)-3-(pyridin-3-yl)prop-2-en-1-amine | 83665-87-6

• 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: (E)-3-(pyridin-3-yl)prop-2-en-1-amine
• 英文别名: 3-(Pyridin-3-yl)prop-2-en-1-amine；(E)-3-pyridin-3-ylprop-2-en-1-amine
• CAS: 83665-87-6
• 化学式: C₈H₁₀N₂
• 分子量: 134.181
• InChiKey: WZGWOIOGOJYLSM-HNQUOIGGSA-N

物化性质

• 沸点：
  274.3±28.0 °C(Predicted)
• 密度：
  1.053±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (E)-3-(pyridin-3-yl)prop-2-en-1-amine 在 偶氮二异丁腈 、 2-甲基十一烷-2-硫醇 、 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 、 mineral oil 为溶剂， 反应 4.5h， 生成 (1,3-dimethyl-1H-imidazol-3-ium-2-yl)((3R*,4S*)-5-imino-4-(pyridin-3-yl)-1-tosylpyrrolidin-3-yl)dihydroborate
  参考文献：
  名称：

  Synthesis of Diverse Boron-Handled N-Heterocycles via Radical Borylative Cyclization of N-Allylcyanamides

  摘要：

  A synthetic method based on radical borylation/cyclization cascades of N-allylcyanamides was developed to construct diverse boron-substituted N-heterocycles. In the reaction process, the N-heterocyclic carbene-boryl radical underwent a chemo- and regioselective addition to the alkene moiety, followed by cyclization with the N-cyano group. The resulting amide-iminyl radical intermediates underwent further reactions to afford various boron-tethered N-heterocyclic molecules. Further transformations to access synthetically useful building blocks were also demonstrated.

  DOI：

  10.1021/acs.orglett.8b03303
• 作为产物：
  描述：

  tert-butyl N-[(E)-3-pyridin-3-ylprop-2-enyl]carbamate 在 甲醇 、 乙酰氯 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以100%的产率得到(E)-3-(pyridin-3-yl)prop-2-en-1-amine
  参考文献：
  名称：

  铃木交叉偶联反应合成海洋海绵生物碱麦冬蛋白及其类似物

  摘要：

  以铃木偶联反应为关键步骤，描述了天然产物麦冬蛋白的新合成方法。该方法扩展到了吗啡肽和膜糖苷的各种类似物的合成。

  DOI：

  10.1016/s0040-4039(02)00947-4

文献信息

• Regioselective and Stereospecific Cross-Coupling of Primary Allylic Amines with Boronic Acids and Boronates through Palladium-Catalyzed CN Bond Cleavage
  作者：Man-Bo Li、Yong Wang、Shi-Kai Tian

  DOI：10.1002/anie.201109171

  日期：2012.3.19

  The NH2 group serves as an effective leaving group in the palladium‐catalyzed regioselective and stereospecific title reaction (see scheme). The reaction works well with aryl‐ and alkenylboronic acids and aryl‐, alkenyl‐, allyl‐, and benzylboronates, and complete transfer of chirality has been achieved when using α‐chiral primary allylic amines as the allylic electrophiles.

  NH 2 基团是钯催化的区域选择性和立体特异性标题反应中有效的离去基团（请参见方案）。该反应与芳基和烯基硼酸以及芳基，烯基，烯丙基和苄基硼酸酯反应良好，当使用α-手性伯烯丙基胺作为烯丙基亲电试剂时，已经实现了手性的完全转移。
• Catalytic Allylation of Stabilized Phosphonium Ylides with Primary Allylic Amines
  作者：Xian-Tao Ma、Yong Wang、Rui-Han Dai、Cong-Rong Liu、Shi-Kai Tian

  DOI：10.1021/jo401736k

  日期：2013.11.1

  A range of ketone-stabilized phosphonium ylides were allylated with high regioselectivity by primary allylic amines in the presence of 5 mol % Pd(PPh3)4 and 10 mol % B(OH)3, and subsequent one-pot Wittig olefination gave structurally diverse α,β-unsaturated ketones in good to excellent overall yields with excellent E selectivity. The one-pot allylation/olefination reaction was extended to ester- and

  在5 mol％Pd（PPh 3）4和10 mol％B（OH）3的存在下，通过伯烯丙基胺以高区域选择性将一系列酮稳定化的磷鎓烷基化，然后进行一锅Wittig烯化反应，从而获得结构上的多样性α，β-不饱和酮，具有优异的E选择性，具有良好的总收率或优异的总收率。通过用TsOH取代B（OH）3，将一锅烯丙基化/烯烃化反应扩展到酯和腈稳定的phospho，然后以适当的总收率得到相应的α，β-不饱和酯和腈。
• N-(3-pyridylalkyl)sulfonamide derivative and pharmaceutical preparation containing thereof
  申请人：TERUMO KABUSHIKI KAISHA

  公开号：EP0501876A1

  公开（公告）日：1992-09-02

  Illustrative examples of the N-(3-pyridylalkyl)sulfonamide derivative are represented by the following formulae [II] and [III]: The derivatives are available for a thromboxane A₂ production inhibitor, a thromboxane A₂ antagonist, a prostaglandin H₂ antagonist, an anti-thrombus agent, a thrombus-preventing agent and an anti-allergy agent.

  N-(3-吡啶基烷基)磺酰胺衍生物的举例说明如下公式[II]和[III]所示：这些衍生物可用作血栓素A₂生成抑制剂、血栓素A₂拮抗剂、前列腺素H₂拮抗剂、抗血栓剂、预防血栓剂和抗过敏剂。
• BICYCLIC PYRAZOLE COMPOUNDS AS ANTIBACTERIAL AGENTS
  申请人：Allison Brett D.

  公开号：US20100280240A1

  公开（公告）日：2010-11-04

  Antibacterial compounds, compositions containing them, and methods of use for the inhibition of bacterial activity and the treatment, prevention or inhibition of bacterial infection.

  抗菌化合物，含有它们的组合物，以及用于抑制细菌活性和治疗、预防或抑制细菌感染的使用方法。
• Substituted dipeptide amides
  申请人：G.D. Searle & Co.

  公开号：EP0215297A2

  公开（公告）日：1987-03-25

  The invention relates to novel substituted tyrosyl alanine dipeptide amides of the formula: and the pharmaceutically acceptable acid addition salts thereof wherein R' is hydrogen, lower alkyl, hydroxy, -OCO2 lower alkyl, lower alkoxy, -O(CH2)n- phenyl with the phenyl optionally substituted by halogen, -NO2, -CN, -NH2 or lower alkyl wherein n is 1 to 4; R2 and R' represent lower alkyl, halogen, or lower alkoxy, or either one of R2 or R3 is hydrogen and the other is lower alkyl, lower alkoxy or halogen; R4. R5, R6, R', R8, and R' may be the same or different and represent hydrogen or lower alkyl; and R10 is selected from the group consisting of -(ALK)X where ALK represents alkylene, thioalkylene, oxyalkylene, having 1 to 5 carbon atoms; alkenylene and alkynylene having 2 to 4 carbon atoms; and X represents pyridyl, pyrimidinyl, 9H-fluoren-9-yl, diphenylmethyl, thienyl, carboxy, lower alkoxy carbonyl, substituted phenyl wherein the phenyl substituent is amino, hydroxy, halogen, nitro, methylenedioxy, lower alkyl, carboxy, lower alkoxycarbonyl, lower alkoxy, carboxamide, diloweral- kylamino or X represents phenyl when ALK is not alkylene; or R'° is where p and q are independently 1 to 4; or R9 and R10 together with N is where r and t are independently 1 to 4; v represents an asymmetric carbon that may be racemic or have the D or L configuration; w represents an asymmetric carbon when R7 and R8 are not the same that may be racemic or have the D or L configuration. These compounds are useful as analgesic and/or antihypertensive compounds.

  本发明涉及式中的新型取代酪氨丙氨酸二肽酰胺： 及其药学上可接受的酸加成盐 其中R'是氢、低级烷基、羟基、-OCO2 低级烷基、低级烷氧基、-O(CH2)n-苯基，苯基可任选被卤素、-NO2、-CN、-NH2或低级烷基取代，其中n为1至4；R2和R'代表低级烷基、卤素或低级烷氧基，或者R2或R3中的一个为氢，另一个为低级烷基、低级烷氧基或卤素；R4.R5、R6、R'、R8 和 R' 可以相同或不同，代表氢或低级烷基；以及 R10 选自以下组成的组-(ALK)X 其中 ALK 代表具有 1 至 5 个碳原子的亚烷基、硫代烷基、氧代烷基；具有 2 至 4 个碳原子的烯基和炔基；X代表吡啶基、嘧啶基、9H-芴-9-基、二苯基甲基、噻吩基、羧基、低级烷氧基羰基、取代苯基，其中苯基取代基为氨基、羟基、卤素、硝基、亚甲基二氧基、低级烷基、羧基、低级烷氧基羰基、低级烷氧基、羧酰胺、稀释酰基氨基，或者当ALK不是亚烷基时，X代表苯基；或者R'°为 其中 p 和 q 独立地为 1 至 4；或 R9 和 R10 与 N 一起为 其中 r 和 t 独立地为 1 至 4； v 代表不对称碳，可以是外消旋体或具有 D 或 L 构型； 当 R7 和 R8 不相同时，w 代表一个不对称碳，它可能是外消旋的或具有 D 或 L 构型。这些化合物可用作镇痛剂和/或抗高血压化合物。