(E)-1-(1,3-二苯基烯丙基)吡咯烷 | 101132-08-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: (E)-1-(1,3-二苯基烯丙基)吡咯烷
• 英文名称: (E)-1-(1,3-diphenylallyl)pyrrolidine
• 英文别名: (E)-1-(1,3-diphenyl-2-propen-1-yl)pyrrolidine；1-[(E)-1,3-diphenylprop-2-enyl]pyrrolidine
• CAS: 101132-08-5
• 化学式: C₁₉H₂₁N
• 分子量: 263.382
• InChiKey: XCONIJJQUDHKSN-BUHFOSPRSA-N

物化性质

• 熔点：
  79 °C(Solv: methanol (67-56-1))
• 沸点：
  387.9±21.0 °C(Predicted)
• 密度：
  1.078±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  反式肉桂醛 在 盐酸 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 6.0h， 生成 (E)-1-(1,3-二苯基烯丙基)吡咯烷
  参考文献：
  名称：

  α-Secondary Dialkylallylamines from Aminonitriles via the Bruylants Reaction

  摘要：

  实际上鲜为人知的α-次级烯丙胺1，通过烯丙胺腈7与格氏试剂反应，已成功合成，产率良好至非常良好。该反应具有区域和立体选择性，并且也能够使用α-氨基腈9和乙烯基格氏试剂进行。

  DOI：

  10.1055/s-1985-31330

文献信息

• Allylic Amination via Decarboxylative C-N Bond Formation
  作者：Jon A. Tunge、Shelli R. Mellegaard-Waetzig、Dinesh Kumar Rayabarapu

  DOI：10.1055/s-2005-918949

  日期：——

  This manuscript details the development of a palladium-catalyzed allylic amination that proceeds via decarboxylation of ­allylic carbamates. Both saturated and aromatic heterocycles undergo decarboxylative rearrangement in good yields. The mechanism of allylation of heteroaromatic amines involves the formation of π-allyl palladium complexes followed by decarboxylation of the ­carbamate. Finally, the heteroaromatic anion equivalent is allylated to provide allylic amines.

  这篇手稿详细描述了一种通过去羧化烯丙基碳酸酯进行的钯催化烯丙基胺化反应。饱和和芳香杂环在良好产率下经历去羧 rearrangement。杂芳香胺的烯丙基化机理涉及 π-烯丙基钯络合物的形成，随后是碳酸酯的去羧化。最后，杂芳香阴离子等价物被烯丙基化，生成烯丙基胺。
• Palladium-catalyzed enantioselective allylation in the presence of phosphoramidites derived from (S a)-3-SiMe3-BINOL, (R,S)-semi-TADDOL, and (R,R)-TADDOL
  作者：K. N. Gavrilov、S. V. Zheglov、I. M. Novikov、I. V. Chuchelkin、V. K. Gavrilov、V. V. Lugovsky、I. A. Zamilatskov

  DOI：10.1007/s11172-015-1047-7

  日期：2015.7

  Novel P*- and P-monodentate phosphoramidites of a 1,3,2-dioxaphosphepine series were derived from (S a)-3-trimethylsilyl-BINOL, (R,S)-semi-TADDOL, and (R,R)-TADDOL. Catalytic performance of the synthesized compounds were examined in the Pd-catalyzed asymmetric allylic substitution of (E)-1,3-diphenylallyl acetate: the reaction with dimethyl malonate gave up to 92% ee. The effects of additives of 5,10,15,20-tetraphenylporphyrin and its metal complexes on conversion and enantioselectivity were studied.

  从(S a)-3-三甲基硅基-BINOL、(R,S)-半 TADDOL 和 (R,R)-TADDOL 衍生出了 1,3,2- 二氧磷杂菲系列的新型 P*- 和 P- 单齿磷酰胺。在 Pd 催化的(E)-1,3-二苯基烯丙基乙酸酯的不对称烯丙基取代反应中，考察了合成化合物的催化性能：与丙二酸二甲酯反应的ee高达 92%。研究了 5,10,15,20-四苯基卟啉及其金属复合物添加剂对转化率和对映体选择性的影响。
• Rhenium complex-catalyzed N-allylation and N-benzylation of amines with alcohols
  作者：Rui Umeda、Shiori Shimaoka、Shintaro Mori、Tsubasa Takagishi、Yutaka Nishiyama

  DOI：10.1016/j.tetlet.2023.154412

  日期：2023.4

  When aliphatic amines were allowed to react with allylic alcohols in the presence of a catalytic amount of a rhenium complex, the N-allylation of aliphatic amines efficiently proceeded to give the corresponding N-allyl substituted amines in moderate to good yields. Similarly, the N-benzylation of an amine with benzylic alcohols occurred in the presence of the rhenium catalyst.

  当允许脂肪胺与烯丙醇在催化量的铼配合物存在下反应时，脂肪胺的N-烯丙基化有效地进行，以中等到良好的收率得到相应的N-烯丙基取代的胺。类似地，胺与苯甲醇的N-苯甲基化反应在铼催化剂存在下发生。
• Development of P∗-monodentate diamidophosphites with a C1-symmetric 1,2-diamine backbone: the effects of substituents in the 1,3,2-diazaphospholidine cycle on Pd-catalyzed asymmetric allylations
  作者：Konstantin N. Gavrilov、Alexei A. Shiryaev、Sergey V. Zheglov、Oksana V. Potapova、Ilya V. Chuchelkin、Ivan M. Novikov、Eugenie A. Rastorguev、Vadim A. Davankov

  DOI：10.1016/j.tetasy.2013.02.010

  日期：2013.4

  We have designed and synthesized a small library of modular monodentate diamidophosphite ligands with stereogenic phosphorus atoms. The library was prepared efficiently from the commercially available and inexpensive (S)-N-Boc-amino acids. These novel ligands were screened in the Pd-catalyzed asymmetric allylations of (E)-1,3-diphenylallyl acetate with dimethyl malonate as the C-nucleophile with up to 93% ee being obtained. The results showed that the different substituents in the 1,3,2-diazaphospholidine cycle had remarkable effects on the enantioselectivity. (c) 2013 Elsevier Ltd. All rights reserved.
• AHLBRECHT, H.;DOLLINGER, H., SYNTHESIS, BRD, 1985, N 8, 743-748
  作者：AHLBRECHT, H.、DOLLINGER, H.

  DOI：——

  日期：——