1-(2-乙基-1-丁烯基)吡咯烷 | 66685-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(2-乙基-1-丁烯基)吡咯烷
• 英文名称: 1-Pyrrolidino-2-aethyl-buten-(1)
• 英文别名: 1-(2-Ethyl-1-butenyl)-pyrrolidine；1-(2-ethylbut-1-enyl)pyrrolidine
• CAS: 66685-15-2
• 化学式: C₁₀H₁₉N
• 分子量: 153.268
• InChiKey: NMCUYNPUEJQBIW-UHFFFAOYSA-N

物化性质

• 沸点：
  71-72 °C(Press: 11 Torr)
• 密度：
  0.928±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-(2-乙基-1-丁烯基)吡咯烷 在 sodium hydroxide 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 双氧水 作用下， 生成 2-乙基-1-丁醇
  参考文献：
  名称：

  Fisher, Gary B.; Juarez-Brambila, Jesus J.; Gorakki, Christian T., Journal of the American Chemical Society, 1993, vol. 115, # 2, p. 440 - 444

  摘要：

  DOI：
• 作为产物：
  描述：

  四氢吡咯 、 2-乙基丁醛 在 4 A molecular sieve 作用下， 反应 0.02h， 以76%的产率得到1-(2-乙基-1-丁烯基)吡咯烷
  参考文献：
  名称：

  Unusual directive effects in the hydroboration of .beta.,.beta.-disubstituted enamines. Conversion of .alpha.-substituted aldehydes to the corresponding alkenes and .beta.-amino alcohols

  摘要：

  A comprehensive study of the conversion of beta,beta-disubstituted enamines into the corresponding alkenes and beta-amino alcohols by hydroboration-elimination and hydroboration-oxidation, respectively, has been carried out. The amine moiety of beta,beta-disubstituted enamines was found to exert a decisive influence on the regioselectivity of the hydroboration reaction involving borane methyl sulfide (BMS). Thus, in the hydroboration of morpholino and piperidino enamines, the boron atom is initially placed predominantly in the alpha-position. Conversely, the pyrrolidino enamines direct the boron atom exclusively to the beta-position. Three oxidizing agents, trimethylamine N-oxide, sodium perborate, and 30% hydrogen peroxide-solid sodium hydroxide, were tried in order to optimize the oxidation of the intermediate organoborane derivatives to the corresponding amino alcohols. Our results clearly indicated that 30% hydrogen peroxide-solid sodium hydroxide is best suited for this transformation. The yield of amino alcohol ranged from good to essentially quantitative. Enamines derived from beta-aryl aldehydes, upon hydroboration with BMS followed by methanolysis and oxidation with neutral hydrogen peroxide, gave the corresponding 1,1-disubstituted alkenes. Contrary to the regioselectivity observed in the hydroboration reactions involving BMS, the hydroboration of beta,beta-disubstituted enamines using 9-borabicyclo[3.3.1]nonane (9-BBN) gave the trialkylborane intermediates in which the boron atom was placed exclusively at the beta-position regardless of the amine moiety of the enamine. These trialkylborane derivatives were very stable and did not undergo the usual elimination reaction with either methanol or sodium hydroxide. However, on thermal decomposition, these afforded the corresponding 1,1-disubstituted alkenes in high yields.

  DOI：

  10.1021/jo00019a043

文献信息

• Synthesis of New 4,4a-Dihydroxanthones via [4+2]-Cycloaddition Reaction
  作者：N. M. Chernov、T. V. Moroz、R. V. Shutov、N. N. Kuz’mich、A. E. Shchegolev、M. V. Sopova、I. P. Yakovlev

  DOI：10.1134/s1070363219120223

  日期：2019.12

  The effect of electronic properties of substituents in the reactants on the [4+2]-cycloaddition of 3-vinyl-chromen-4-ones (dienes) and N-vinylpyrrolidines (dienophiles) has been studied. The conditions determining the formation of 4,4a-dihydroxanthones or benzophenones as the major products have been found. The aromatization of 4,4a-dihydroxanthones via pyran ring opening has been interpreted by quantum

  已经研究了反应物中取代基的电子性质对3-乙烯基色烯-4-酮（二烯）和N-乙烯基吡咯烷酮（二亲亲烯）的[4 + 2]-环加成的影响。已经发现确定形成4,4a-二氢黄嘌呤或二苯甲酮作为主要产物的条件。通过吡喃开环将4,4a-二氢氧杂蒽芳构化已通过量子化学计算进行了解释。已分离出一系列新的4,4a-二氢黄酮和二苯甲酮衍生物。
• New indium-mediated reactions of enamines
  作者：Fabienne Bossard、Valéry Dambrin、Valérie Lintanf、Pierre Beuchet、Paul Mosset

  DOI：10.1016/0040-4039(95)01241-9

  日期：1995.8

  New reactions of enamines were observed with allyl bromide or methyl bromoacetate in the presence of indium powder in THF, yielding respectively homoallylamines and β-aminoesters.

  在铟粉在THF中的存在下，观察到烯胺与烯丙基溴或溴乙酸甲酯的新反应，分别得到高烯丙基胺和β-氨基酯。
• An electrochemical access to 2-amino-2,3-dihydro-1,4-benzodioxanes derived from hydroxytyrosol
  作者：Anne Neudorffer、Patrick Deschamps、Martine Largeron、Brigitte Deguin

  DOI：10.1039/d3ob01858j

  日期：——

  The anodic oxidation of a natural antioxidative catechol, hydroxytyrosol, was developed in an acetonitrile/dimethylsulfoxide (or acetonitrile/water) solvent mixture to produce in a stable way the resulting non-activated o-quinone and generate structural analogues. 2-Amino-2,3-dihydro-1,4-benzodioxane derivatives were obtained as two regioisomers in good to high overall yields (65–90%) and 1 : 3 ratios

  天然抗氧化儿茶酚羟基酪醇的阳极氧化是在乙腈/二甲亚砜（或乙腈/水）溶剂混合物中开发的，以稳定的方式产生所得的非活化邻醌并产生结构类似物。通过逆电子需求 Diels-Alder (IEDDA)，以良好到高的总产率 (65–90%) 和 1:3 的比例获得了两种区域异构体形式的 2-氨基-2,3-二氢-1,4-苯并二恶烷衍生物电生成的邻醌和叔烯胺之间的反应。在儿茶酚上插入吸电子（或供电子）基团改变了它们的相对比例，从而使反应变得区域特异性。与一些脂肪族烯胺发生竞争性1,6-迈克尔加成，得到2-羟基-1,2,4,5-四氢苯并[ d ]氧杂环己烷化合物。
• Unusual directive effects in the hydroboration of .beta.,.beta.-disubstituted enamines. Conversion of .alpha.-substituted aldehydes to the corresponding alkenes and .beta.-amino alcohols
  作者：Bakthan Singaram、Christian T. Goralski、Gary B. Fisher

  DOI：10.1021/jo00019a043

  日期：1991.9

  A comprehensive study of the conversion of beta,beta-disubstituted enamines into the corresponding alkenes and beta-amino alcohols by hydroboration-elimination and hydroboration-oxidation, respectively, has been carried out. The amine moiety of beta,beta-disubstituted enamines was found to exert a decisive influence on the regioselectivity of the hydroboration reaction involving borane methyl sulfide (BMS). Thus, in the hydroboration of morpholino and piperidino enamines, the boron atom is initially placed predominantly in the alpha-position. Conversely, the pyrrolidino enamines direct the boron atom exclusively to the beta-position. Three oxidizing agents, trimethylamine N-oxide, sodium perborate, and 30% hydrogen peroxide-solid sodium hydroxide, were tried in order to optimize the oxidation of the intermediate organoborane derivatives to the corresponding amino alcohols. Our results clearly indicated that 30% hydrogen peroxide-solid sodium hydroxide is best suited for this transformation. The yield of amino alcohol ranged from good to essentially quantitative. Enamines derived from beta-aryl aldehydes, upon hydroboration with BMS followed by methanolysis and oxidation with neutral hydrogen peroxide, gave the corresponding 1,1-disubstituted alkenes. Contrary to the regioselectivity observed in the hydroboration reactions involving BMS, the hydroboration of beta,beta-disubstituted enamines using 9-borabicyclo[3.3.1]nonane (9-BBN) gave the trialkylborane intermediates in which the boron atom was placed exclusively at the beta-position regardless of the amine moiety of the enamine. These trialkylborane derivatives were very stable and did not undergo the usual elimination reaction with either methanol or sodium hydroxide. However, on thermal decomposition, these afforded the corresponding 1,1-disubstituted alkenes in high yields.
• Kuhlmey,S.-R. et al., Liebigs Annalen der Chemie, 1979, p. 617 - 627
  作者：Kuhlmey,S.-R. et al.

  DOI：——

  日期：——