3-pyrrolidinopent-2-ene | 56176-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-pyrrolidinopent-2-ene
• 英文别名: (E)-1-Pyrrolidino-2-pentene；1-[(E)-pent-2-en-3-yl]pyrrolidine
• CAS: 56176-59-1
• 化学式: C₉H₁₇N
• 分子量: 139.241
• InChiKey: LSQXOLFOAOCMSS-YCRREMRBSA-N

物化性质

• 沸点：
  200.3±7.0 °C(Predicted)
• 密度：
  0.887±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-pyrrolidinopent-2-ene 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 3-Ethyl-4-furan-2-yl-2-methyl-cyclopent-2-enone
  参考文献：
  名称：

  [3 + 2] Cycloaddition of Fischer Alkenyl Carbene Complexes to Enamines:  An Efficient Asymmetric Approach to Cyclopentanoids

  摘要：

  DOI：

  10.1021/ja9825736
• 作为产物：
  描述：

  3-戊酮 、 四氢吡咯 以 甲苯 为溶剂， 生成 3-pyrrolidinopent-2-ene
  参考文献：
  名称：

  On the Formation and Reactivity of 2-Alkylidene-benzopyrans and their 2-amino-5,6-benzo-2H-pyran precursors

  摘要：

  A series of 2-amino-substituted 5,6-benzo-2H-pyrans 14, 2-alkylidene-5,6-benzo-2H-pyrans 15, and their dimers 17 are obtained, depending on the condition used, by the reaction of 2-hydroxy-benzaldehydes I with enamines 9 derived of (cyclo)aliphatic ketones. Compounds 14, 15, and 17 can be transformed into 2-alkyl-benzopyrylium salts 16 or 2-[1-(2-hydroxyphenyl)-alken-2-yl]-benzopyrylium salts 23 by treatment with mineral acids. With aromatic aldehydes or the Vilsmeier reagent the compounds 14, 15, or 17 are transformed into deeply colored 2-(aryl-alkenyl)-benzopyrylium perchlorates 25 or 2-(2-dialkylamino)-alkenyl-benzopyrylium salts 26, respectively.

  DOI：

  10.1002/prac.19983400106

文献信息

• An enamine method for the synthesis of 1-azaazulene derivatives. Reactions of troponimines with enamines 1
  作者：Tohru Takayasu、Makoto Nitta

  DOI：10.1039/a809700c

  日期：——

  A short new synthesis of 1-azaazulene derivatives consists of the enamine alkylation of troponimines 4–7 with pyrrolidino enamines, which are derived from cycloalkanones, aliphatic ketones, and heterocyclic ketones, to lead to formal [8 + 2] cycloadducts and subsequent aromatization under the reaction conditions. The reactions are quite general, and N-hydroxy- and N-methoxytroponimines, 4 and 5, are less reactive than N-mesyloxy- and N-tosyloxytroponimines, 6 and 7, which react smoothly even at room temperature. In the reaction of the pyrrolidino enamine, which is derived from cyclopentanone, forcing conditions are required, probably because of ring strain in the [8 + 2] cycloadduct 11a. Furthermore, in the reactions of 4–7 with isomeric mixtures of two pyrrolidino enamines, 15/16 and 20/21, only enamines 15 and 20 can intervene in the cycloaddition reactions, giving 1-azaazulene derivatives. In the context of the reactivity of 4–7 and pyrrolidino enamines, and the selectivity observed in the reactions with isomeric mixtures of enamines, minimal neglect of differential overlap (MNDO) calculations on troponimines 4–7 and pyrrolidino enamines, as well as isomeric mixtures of two enamines, 15/16 and 20/21, were performed to gain further insight into the reactions via a theoretical interpretation based upon frontier molecular orbital theory (FMO). Troponimines 6 and 7 have lower LUMOs and they are more reactive than troponimines 4 and 5; the energy level of the HOMO of the pyrrolidino enamine derived from cyclopentanone is relatively higher as compared to those of other pyrrolidino enamines. Enamines 15 and 20 are less stable and energy levels of the HOMOs are higher as compared with those of the corresponding isomers 16 and 21, respectively.

  一种新的短链合成1-氮基藍烯衍生物的方法包括对4-7号烃基化的氨基萘酮与源自环烷酮、脂肪酮和杂环酮的吡咯烯胺进行反应，从而产生形式上的[8 + 2]环加成物，并在反应条件下随后发生芳香化。这些反应相当普遍，其中N-羟基和N-美克酮基的氨基萘酮4和5的反应性较低，而N-美克酯基和N-苯磺酯基的氨基萘酮6和7则在室温下也能顺利反应。在从环戊酮衍生的吡咯烯胺的反应中，需采取强迫条件，这可能是由于[8 + 2]环加成物11a的环应变。此外，在4-7号与两种异构体的吡咯烯胺混合物15/16和20/21反应时，只有吡咯烯胺15和20能参与环加成反应，生成1-氮基蓝烯衍生物。针对4-7号和吡咯烯胺的反应性，以及在与异构体的吡咯烯胺混合物反应中观察到的选择性，进行了最小忽略微分重叠（MNDO）计算，以进一步深入理解反应，通过基于前沿分子轨道理论（FMO）的理论解释。氨基萘酮6和7的低空态分子轨道（LUMO）更低，反应性比氨基萘酮4和5更强；源自环戊酮的吡咯烯胺的高占据分子轨道（HOMO）能量水平相对较高。吡咯烯胺15和20相对不稳定，其高占据分子轨道的能量水平较对应异构体16和21更高。
• Synthesis of 1<i>H</i>-2-Benzopyran-5,8-dione Derivatives from 2-(1-Hydroxy­alkyl)-1,4-benzoquinones and Enamines
  作者：Kazuhiro Kobayashi、Kosaku Nomura、Toshikazu Ogata、Miyuki Tanmatsu、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1055/s-2003-38066

  日期：——

  An efficient synthesis of the title benzopyranodione derivatives based on a Michael addition/cyclization sequence between 2-(1-hydroxyalkyl)-1,4-benzoquinones and enamines (or an imine) is described.

  本文描述了一种高效合成标题苯并吡喃二酮衍生物的方法，该方法基于2-(1-羟基烷基)-1,4-苯醌与烯胺（或亚胺）之间的迈克尔加成/环化反应序列。
• Synthesis and Reactions of Haloazodienes. A New and General Synthesis of Substituted Pyridazines
  作者：Michael S. South、Terri L. Jakuboski、Mark D. Westmeyer、Daniel R. Dukesherer

  DOI：10.1021/jo960029e

  日期：1996.1.1

  tetrahydropyridazines that are formed give high yields of substituted pyridazines upon treatment with base (Table 1). The sequence of a chloroazodiene cyclization to a tetrahydropyridazine followed by an aromatization constitutes a new and general synthesis of substituted pyridazines. In contrast to the haloazodiene cyclizations, the novel cyclization reactions of the in-situ generated 1-carbethoxy-3-phenyl-4

  二卤代azo唑与Hünig碱的反应原位生成1-carbethoxy-3-phenyl-4-haloazodiedienes，发现它们与多种富电子烯烃结合生成卤代四氢哒嗪（方案2和表1）。这些卤代偶氮二烯环化的最佳特征是反电子需求，4 + 2杂Diels-Alder反应，可维持高度的区域和立体化学控制（方案5和6）。形成的氯取代的四氢哒嗪在用碱处理后可得到高产率的取代的哒嗪（表1）。氯偶氮二烯环化成四氢哒嗪并随后进行芳构化的顺序构成了取代的哒嗪的新的通用合成方法。与卤代偶氮二烯环化不同，当与无环烯胺结合时，发现原位产生的1-碳乙氧基-3-苯基-4，4-二氯偶氮二烯的新型环化反应产生N-氨基吡咯和哒嗪（表3）。然而，与环状烯胺的反应产生了N-氨基吡咯，哒嗪，二氢哒嗪作为产物以及未环化的烯胺中间体（表4）。仅加热至更高的温度，未环化的烯胺即可转化为N-氨基吡咯，表明其机理是逐步的（方案8和9）。
• THE FACILE SYNTHESIS OF 1- AND 2-ALKYLAZULENES BY THE REACTIONS OF 2<i>H</i>-CYCLOHEPTA[<i>b</i>]FURAN-2-ONES WITH ENAMINES OF ALDEHYDES AND ACYCLIC KETONES
  作者：Masafumi Yasunami、Alice Chen、P. W. Yang、Kahei Takase

  DOI：10.1246/cl.1980.579

  日期：1980.5.5

  The reactions of 2H-cyclohepta[b]furan-2-one and its 3-cyano derivatives with enamines derived from aldehydes and acyclic ketones were investigated. On the reactions, 1- and 2-alkylazulenes were easily synthesized.

  研究了 2H-cyclohepta[b]furan-2-one 及其 3-氰基衍生物与衍生自醛和无环酮的烯胺的反应。在反应中，很容易合成 1- 和 2- 烷基甘菊烯。
• New Synthesis of Amines and Amides Mediated by Additions of Benzotriazole to Enamines and Enamides and Transformations of the Adducts
  作者：Alan R. Katritzky、Simona Jurczyk、Bogumila Rachwal、Stanislaw Rachwal、Irina Shcherbakova、Konstantina Yannakopoulou

  DOI：10.1055/s-1992-26362

  日期：——

  Adducts of type N-C-Bt can be obtained in which the nitrogen atom is derived from an N-vinyl non-basic heterocyclic NH compound or a secondary amide, or in which the central carbon is derived from a ketone by the addition of benzotriazole to an enamine or enamide. Thus, 9-vinylcarbazole, 1-vinylpyrrolidin-2-one and 1-(1-ethylprop-1-enyl)pyrrolidine afforded the corresponding N-(1-benzotriazolylalkyl)-substituted compounds which could be alkylated by various methods in good yield. The range of benzotriazole mediated syntheses of amines and amides is significantly extended in this way.

  可以获得类型为 N-C-Bt 的加成物，其中氮原子来源于 N-乙烯基非碱性杂环 NH 化合物或次级酰胺，或其中中心碳原子通过将苯并三唑加到烯胺或烯酰胺中而来源于酮。因此，9-乙烯基卡巴唑、1-乙烯基吡咯烷-2-酮和 1-(1-乙基丙-1-烯基)吡咯烷提供了相应的 N-(1-苯并三唑基烷基)取代化合物，这些化合物可以通过多种方法进行烷基化，产率良好。通过这种方式，苯并三唑介导的胺和酰胺的合成范围显著扩大。

表征谱图