ethyl 2-(2-([1,1′-biphenyl]-4-yl-ethynyl)pyrrolidin-1-yl)acetate | 1206905-77-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(2-([1,1′-biphenyl]-4-yl-ethynyl)pyrrolidin-1-yl)acetate
• 英文别名: ethyl 2-(2-(2-(4-phenylphenyl)ethynyl)pyrrolidin-1-yl)acetate；Ethyl 2-[2-[2-(4-phenylphenyl)ethynyl]pyrrolidin-1-yl]acetate
• CAS: 1206905-77-2
• 化学式: C₂₂H₂₃NO₂
• 分子量: 333.43
• InChiKey: UDIBKWDXGNUCQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-([1,1′-biphenyl]-4-yl-ethynyl)pyrrolidin-1-yl)acetate 在 N-甲基吗啉 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以52%的产率得到ethyl 2-(2-([1,1′-biphenyl]-4-yl)-4H-thieno[3,2-b]pyrrol-4-yl)acetate
  参考文献：
  名称：

  元素硫结合的吡咯烷并噻吩并吡咯类化合物的环化反应。

  摘要：

  我们在本文中报道了2-炔基吡咯烷与元素硫的直接氧化[4 + 1]环化反应合成噻吩并[3,2- b ]吡咯。该转变可能源自吡咯烷在β-位的亲电攻击，随后是分子内的噻吩环化以递送所需的产物。机理研究表明，该反应涉及二氢噻吩并[3，2- b ]吡咯作为中间体的形成。

  DOI：

  10.1021/acs.joc.0c01363
• 作为产物：
  描述：

  乙醛酸乙酯 、 4-乙炔联苯 、 DL-脯氨酸 在 N,N-二异丙基乙胺 、 copper(I) bromide 作用下， 以 甲苯 为溶剂， 以64%的产率得到ethyl 2-(2-([1,1′-biphenyl]-4-yl-ethynyl)pyrrolidin-1-yl)acetate
  参考文献：
  名称：

  Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp³−Csp) of Natural α-Amino Acids and Alkynes

  摘要：

  An interesting aldehyde- and ketone-induced intermolecular tandem decarboxylation-coupling (Csp(3)-Csp) catalyzed by copper with use of natural alpha-amino acids as starting materials is developed under neutral conditions with the production of CO2 and H2O as the only by products. Various functionalized nitrogen-containing compounds were obtained by this method. In these processes, interesting regioselectivites of the alkylation were observed, which has been rationalized by the relative stability of proposed resonance structures based on computation methods.

  DOI：

  10.1021/jo902319h

文献信息

• Elemental-Sulfur-Incorporated Cyclizations of Pyrrolidines Leading to Thienopyrroles
  作者：Yuanyuan Yue、Huibin Shao、Zhixian Wang、Ke Wang、Le Wang、Kelei Zhuo、Jianming Liu

  DOI：10.1021/acs.joc.0c01363

  日期：2020.9.4

  2-b]pyrroles from the direct oxidative [4 + 1] cyclization of 2-alkynyl pyrrolidines with elemental sulfur. This transformation likely originates from electrophilic attack at the β-position of pyrrolidine followed by an intramolecular thienannulation to deliver the desired product. Mechanistic investigation suggests that the present reaction involves the formation of dihydrothieno[3,2-b]pyrrole as an

  我们在本文中报道了2-炔基吡咯烷与元素硫的直接氧化[4 + 1]环化反应合成噻吩并[3,2- b ]吡咯。该转变可能源自吡咯烷在β-位的亲电攻击，随后是分子内的噻吩环化以递送所需的产物。机理研究表明，该反应涉及二氢噻吩并[3，2- b ]吡咯作为中间体的形成。
• Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp³−Csp) of Natural α-Amino Acids and Alkynes
  作者：Hai-Peng Bi、Qingfeng Teng、Min Guan、Wen-Wen Chen、Yong-Min Liang、Xiaojun Yao、Chao-Jun Li

  DOI：10.1021/jo902319h

  日期：2010.2.5

  An interesting aldehyde- and ketone-induced intermolecular tandem decarboxylation-coupling (Csp(3)-Csp) catalyzed by copper with use of natural alpha-amino acids as starting materials is developed under neutral conditions with the production of CO2 and H2O as the only by products. Various functionalized nitrogen-containing compounds were obtained by this method. In these processes, interesting regioselectivites of the alkylation were observed, which has been rationalized by the relative stability of proposed resonance structures based on computation methods.