1-(2,2-二苯基乙烯基)吡咯烷 | 13150-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2,2-二苯基乙烯基)吡咯烷
• 中文别名: 吡咯烷,1-(2,2-二苯基乙烯基)-
• 英文名称: 1,1-Diphenyl-2-pyrrolidinoethene
• 英文别名: 1-(2',2'-diphenylvinyl)pyrrolidine；1-(2,2-diphenyl-1-ethenyl)-pyrrolidine；1-(2,2-Diphenylethenyl)pyrrolidine
• CAS: 13150-54-4
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: MKRGHDHOOAAPPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  1-(2,2-二苯基乙烯基)吡咯烷 在 dimethyl sulfide borane 、 双氧水 作用下， 生成 1,1-二苯乙烯
  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
• 作为产物：
  描述：

  四氢吡咯 、 联苯乙醛 以 氯仿 为溶剂， 反应 1.0h， 以64%的产率得到1-(2,2-二苯基乙烯基)吡咯烷
  参考文献：
  名称：

  Highly Chemoselective Formation of Aldehyde Enamines under Very Mild Reaction Conditions

  摘要：

  Although ketone enamines are widely used in organic synthesis, aldehyde enamines are rarely employed due to the limitations of their preparation using known methods (need for acid or base, excess of amine, and/or elevated temperature). We have successfully developed rapid and particularly mild condensation conditions (1 h, 0 degrees C, 1.2 equiv of amine) leading to di- and trisubstituted enamines with excellent conversion (84-100%). Remarkably high chemoselectivity was observed with complete discrimination between aldehyde and ketone, among other functional groups positively tested.

  DOI：

  10.1021/jo0611061
• 作为试剂：
  描述：

  正癸烯 、 全氟己基碘烷 在 1-(2,2-二苯基乙烯基)吡咯烷 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以100%的产率得到1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodohexadecane
  参考文献：
  名称：

  含フッ素化合物の製造方法

  摘要：

  提供一种制备含氟化合物的方法，通过对工业上可行的烯烃进行全氟烷基自由基的加成反应。在有机溶剂中，存在吡啶化合物和醛化合物生成的恩酰胺衍生物的情况下，将式（2）的烯烃和R8-I（R8代表三氟甲基基、五氟乙基基、C3-C8的直链/支链/环式等全氟烷基）的含氟有机碘化合物，在光照射下反应，特征是含氟化合物的制备方法。（R4-R6独立地表示氢、甲基、乙基、C3-C10的直链烷基、末端带有羟基的C2-C6的烷基、苯基、甲氧基羰基、乙氧基羰基、2-异丙基脱氢脂环丁-2-基氧羰基或异丙烯-2-基氧羰基等）【选择图】无

  公开号：

  JP2019151570A

文献信息

• 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.
• Highly Chemoselective Formation of Aldehyde Enamines under Very Mild Reaction Conditions
  作者：Guillaume Bélanger、Michaël Doré,、Frédéric Ménard、Véronique Darsigny

  DOI：10.1021/jo0611061

  日期：2006.9.1

  Although ketone enamines are widely used in organic synthesis, aldehyde enamines are rarely employed due to the limitations of their preparation using known methods (need for acid or base, excess of amine, and/or elevated temperature). We have successfully developed rapid and particularly mild condensation conditions (1 h, 0 degrees C, 1.2 equiv of amine) leading to di- and trisubstituted enamines with excellent conversion (84-100%). Remarkably high chemoselectivity was observed with complete discrimination between aldehyde and ketone, among other functional groups positively tested.