2-benzyl-4,4-dimethylpyrrolidine | 500352-84-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-benzyl-4,4-dimethylpyrrolidine
• 英文别名: Pyrrolidine, 4,4-dimethyl-2-(phenylmethyl)-
• CAS: 500352-84-1
• 化学式: C₁₃H₁₉N
• 分子量: 189.301
• InChiKey: XLUMTXJLIZESLW-UHFFFAOYSA-N

物化性质

• 沸点：
  263.6±9.0 °C(Predicted)
• 密度：
  0.939±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-benzyl-4,4-dimethylpyrrolidine 、 对甲苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以32 mg的产率得到2-benzyl-4,4-dimethyl-1-tosylpyrrolidine
  参考文献：
  名称：

  Substrate Structural Effects in Yttrium(III)-Catalyzed Hydroamination/Cyclizations of 1,2-Disubstituted and 1,1,2-Trisubstituted Aminoalkenes ­Terminated by 2-(Phenyl) and 2-(2-Heteroarenyl) Groups

  摘要：

  A series of 2-phenyl- and 2-(2-heteroarenyl)-bearing amines possessing 1,2-disubstituted and 1,1,2-trisubststuted alkenes have been evaluated in intramolecular hydroaminations catalyzed by Y[N(TMS)(2)](3) (1(Y)). Aminoalkenes possessing a terminal 2-(5-trimethylsilyl)thienyl group exhibited substantially enhanced reactivity compared to their 2-(phenyl)-containing counterparts. Cyclization efficiencies imparted by the 2-[(5-trimethylsilyl) furanyl] substituent were comparable or only slightly better than those obtained with the simple the 2-(phenyl) group.

  DOI：

  10.1055/s-0032-1317843
• 作为产物：
  描述：

  肉桂基氯 在 bis(trimethylsilyl)amide yttrium(III) 、 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 氘代苯 为溶剂， 反应 16.0h， 生成 2-benzyl-4,4-dimethylpyrrolidine
  参考文献：
  名称：

  Substrate Structural Effects in Yttrium(III)-Catalyzed Hydroamination/Cyclizations of 1,2-Disubstituted and 1,1,2-Trisubstituted Aminoalkenes ­Terminated by 2-(Phenyl) and 2-(2-Heteroarenyl) Groups

  摘要：

  A series of 2-phenyl- and 2-(2-heteroarenyl)-bearing amines possessing 1,2-disubstituted and 1,1,2-trisubststuted alkenes have been evaluated in intramolecular hydroaminations catalyzed by Y[N(TMS)(2)](3) (1(Y)). Aminoalkenes possessing a terminal 2-(5-trimethylsilyl)thienyl group exhibited substantially enhanced reactivity compared to their 2-(phenyl)-containing counterparts. Cyclization efficiencies imparted by the 2-[(5-trimethylsilyl) furanyl] substituent were comparable or only slightly better than those obtained with the simple the 2-(phenyl) group.

  DOI：

  10.1055/s-0032-1317843

文献信息

• N,N′-Dibenzosuberyl-1,1′-Binaphthyl-2,2′-diamine: A Highly Effective Supporting Ligand for the Enantioselective Cyclization of Aminoalkenes Catalyzed by Chelating Diamide Complexes of La(III) and Y(III)
  作者：Tom Livinghouse、Khoi Huynh、Helena Lovick

  DOI：10.1055/s-0033-1340186

  日期：——

  Enantioselective hydroamination/cyclization of representative aminoalkenes catalyzed by chelating diamide complexes of La(III) and Y(III) are described. It is noteworthy that the La(III) complex derived from the sterically demanding ( R )- N , N ′-dibenzosuberyl-1,1′-binaphthyl-2,2′-diamine proligand provides enantioselectivities that are in many cases significantly higher than those obtained with

  描述了由螯合 La(III) 和 Y(III) 的二酰胺配合物催化的代表性氨基烯烃的对映选择性加氢胺化/环化。值得注意的是，由空间要求高的 (R)-N , N '-dibenzosuberyl-1,1'-binaphthyl-2,2'-diamine proligand 衍生的 La​​(III) 配合物提供的对映选择性在许多情况下显着高于那些用相应的 Y(III) 类似物获得的。此外，与 La(III) 对应物相比，LiCl 的存在通常会抑制 Y(III) 配合物获得的速率和对映选择性，此外还完全抑制 7b 的双环化。后一项研究中使用的酰胺配合物是通过使用新的高活性碱 La[N(TMS)(t-Bu)] 3 和 Y[N(TMS)( t-Bu)] 3 通过“胺消除”制备的。
• Base-catalysed asymmetric hydroamination/cyclisation of aminoalkenes utilising a dimeric chiral diamidobinaphthyl dilithium salt
  作者：Patricia Horrillo Martínez、Kai C. Hultzsch、Frank Hampel

  DOI：10.1039/b518360j

  日期：——

  A dimeric proline derived diamidobinaphthyl dilithium salt represents the first example of a chiral main group metal based catalyst for asymmetric hydroamination/cyclisation reactions of aminoalkenes.

  二聚脯氨酸衍生的二氨基联萘基二锂盐代表用于氨基烯烃的不对称加氢胺化/环化反应的手性主族金属基催化剂的第一个实例。
• <i>C₁ </i> -symmetric β-Diketiminatoiron(II) Complexes for Hydroamination of Primary Alkenylamines
  作者：Clément Lepori、Régis Guillot、Jérôme Hannedouche

  DOI：10.1002/adsc.201801464

  日期：2019.2.19

  The synthesis and solid‐state characterization of an array of well‐defined low‐coordinate C1‐symmetric β‐diketiminatoiron(II) alkyl complexes B3–B6 featuring steric and electronic variations on one of the N‐aryl substituents of the β‐diketiminate ligand scaffold are reported. All complexes display unique catalytic abilities of promoting the selective exo‐cyclohydroamination of unprotected 2,2‐diph

  一系列定义明确的低坐标C 1对称β-二酮基亚铁（II）烷基配合物B 3 - B 6的合成和固态表征，其β的N-芳基取代基之一具有空间和电子变异报道了二二酮配体支架。所有复合物显示促进选择性的独特的催化能力外未保护的2,2- diphenylpent -4-烯-1-胺（的-cyclohydroamination 1轻微的反应条件下）。在N之一上掺入潜在配位的邻甲氧基取代基β-二酮骨架的芳基环与另一个拥挤的2,6-二异丙基苯基结合，可提供比我们先前报道的C 2对称β-二酮基体铁（II）更活泼的催化剂（B 3）烷基络合物B（Ar 1 = Ar 2 = 2,4,6-（Me）3 C 6 H 2）/环戊基胺体系。通过比较研究可以推测，与B 4 - B 6相比，B 3的这种优越活性很可能是由于邻位效应和/或邻位配位能力引起的。-甲氧基取代基。还介绍了这种新颖的C 1对称β-二酮基亚氨基铁（II）烷基络合物B
• A novel chiral yttrium complex with a tridentate linked amido-indenyl ligand for intramolecular hydroamination
  作者：Zhuo Chai、Dezhi Hua、Kui Li、Jiang Chu、Gaosheng Yang

  DOI：10.1039/c3cc47006g

  日期：——

  A new chiral silicon-linked tridentate amido-indenyl ligand was developed from indene and enantiopure 1,2-cyclohexanediamine. Its yttrium complex was synthesized, characterized and applied to efficiently catalyze the intramolecular hydroamination of non-activated olefins with up to 97% ee.

  一种新的手性硅联接的三齿氨基-茚基配体是由茚和对映纯的1,2-环己二胺开发的。其钇配合物被合成、表征，并用于高效催化非活化烯烃的分子内氢氨化反应，获得了高达97%的对映纯度。
• A Chiral Phenoxyamine Magnesium Catalyst for the Enantioselective Hydroamination/Cyclization of Aminoalkenes and Intermolecular Hydroamination of Vinyl Arenes
  作者：Xiaoming Zhang、Thomas J. Emge、Kai C. Hultzsch

  DOI：10.1002/anie.201105079

  日期：2012.1.9

  If Grignard had only known! A chiral magnesium complex catalyzes the intramolecular hydroamination/cyclization of aminoalkenes with high efficiency at temperatures as low as −20 °C and enantioselectivities as high as 93 % ee. The high activity of this system also allows the catalytic intermolecular anti-Markovnikov addition of pyrrolidine and benzylamine to vinyl arenes.

  如果格利雅德只知道！手性镁配合物可在低至-20°C的温度和高达93％ee的对映选择性下高效催化氨基烯烃的分子内加氢胺化/环化反应。该系统的高活性还允许将吡咯烷和苄胺催化分子间抗Markovnikov加成到乙烯基芳烃上。