(S)-1-(diphenyl(pyrrolidin-2-yl)methyl)-4-phenyl-1H-1,2,3-triazole | 1630954-98-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-1-(diphenyl(pyrrolidin-2-yl)methyl)-4-phenyl-1H-1,2,3-triazole
• 英文别名: 1-[diphenyl-[(2S)-pyrrolidin-2-yl]methyl]-4-phenyltriazole
• CAS: 1630954-98-1
• 化学式: C₂₅H₂₄N₄
• 分子量: 380.492
• InChiKey: SZUXBCQLGWJEHA-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-(+)-alpha,alpha-二苯基脯氨醇 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 生成 (S)-1-(diphenyl(pyrrolidin-2-yl)methyl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  In search of diamine analogs of the α,α-diphenyl prolinol privileged chiral organocatalyst. Synthesis of diamine derivatives of α,α-diphenyl-(S)-prolinol and their application as organocatalysts in the asymmetric Michael and Mannich reactions

  摘要：

  This paper describes improved reaction conditions for the substitution of the hydroxyl group in (S)-diphenyl(pyrrolidin-2-yl)methanol by the azide group, which was then reduced to the diamine derivative. We examined two protecting groups (N-Bn and N-Boc) on the pyrrolidine nitrogen in order to functionalize the primary amino group into various amide, alkylated amine, sulfonamide, thiourea and triazole derivatives. Notably, carefully controlled conditions were required to generate the desired derivatives from the sterically hindered benzhydrylamine moiety. Unexpectedly, upon removal of the N-protecting group in derivatives containing electrophilic polar double bonds (C=S, C=O) cyclization took place, affording products such as amidines. The target compounds were evaluated as bifunctional organocatalysts in the asymmetric Michael and Mannich addition reactions. (S)-2-(Azidodiphenylmethyl) pyrrolidine (S)-7 was identified as the most efficient organocatalyst among the various diamine derivatives of alpha,alpha-diphenyl-(S)-prolinol prepared in this work. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.11.032

文献信息

• Entry to Highly Hindered Chiral β-Amino Triazoles Bearing a gem-Diaryl Group by Azide-alkyne Click Chemistry
  作者：Venkata Subbaiah Sadu、Harendra Nath Roy、Pitchaiah Arigala、In-Taek Hwang、Kee-In Lee

  DOI：10.5012/bkcs.2014.35.6.1605

  日期：2014.6.20

  Copper(I)-catalyzed Huisgen cycloaddition of terminal alkynes with unmasked azidoamines derived from amino acids is described. The reported strategy provides a new entry to highly hindered $\beta}$-amino 1,2,3-triazole derivatives bearing a gem-diaryl group, which are potentially valuable entities as molecular catalysts for asymmetric transformations.

  本文描述了由氨基酸衍生的未保护叠氮胺与末端炔烃在铜(I)催化下的Huisgen环加成反应。所报道的策略为高度空间位阻的$\beta}$-氨基-1,2,3-三唑衍生物提供了一条新的合成途径，该衍生物具有一对对称的二芳基基团，可能是有价值的分子催化剂，用于不对称转化。
• Influence of steric demand on ruthenium-catalyzed cycloaddition of sterically hindered azides
  作者：Venkata S. Sadu、Sirisha Sadu、Seji Kim、In-Taek Hwang、Ki-Jeong Kong、Kee-In Lee

  DOI：10.1039/c6ra25403a

  日期：——

  The RuAAC of sterically hindered 2,2-diaryl-2-azidoamines and terminal alkynes resulted in the unprecedented formation of 1,4-disubstituted-1,2,3-triazoles. A control experiment with 2-(azidomethyl)pyrrolidine revealed the usual selectivity with RuAAC and the reactions of azides with intermediate bulkiness gave mixtures of 1,4- and 1,5-regioisomers. The results suggest that the steric demands could

  空间受阻的2,2-二芳基-2-叠氮基胺和末端炔烃的RuAAC导致空前形成1,4-二取代-1,2,3-三唑。用2-（叠氮甲基）吡咯烷的对照实验表明，通常用RuAAC具有选择性，叠氮化物在中等体积下的反应得到1，4-和1，5-区域异构体的混合物。结果表明，空间需求可以基本消除RuAAC的偏好和对区域选择性的影响。