4'-tert-butylphenyl 2-butynoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4'-tert-butylphenyl 2-butynoate
• 英文别名: 4-tert-butylphenyl but-2-ynoate；(4-Tert-butylphenyl) but-2-ynoate；(4-tert-butylphenyl) but-2-ynoate
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: UNJOGBWBQGFMSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4'-tert-butylphenyl 2-butynoate 在 palladium diacetate 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以90%的产率得到4-甲基-6-叔丁基香豆素
  参考文献：
  名称：

  New Method for Preparation of Coumarins and Quinolinones via Pd-Catalyzed Intramolecular Hydroarylation of C−C Triple Bonds

  摘要：

  A new and general method has been developed for preparation of coumarins and quinolinones by intramolecular hydroarylation of alkynes. Various aryl alkynoates and alkynanilides undergo fast intramolecular reaction at room temperature in the presence of a catalytic amount of Pd(OAc)(2) in a mixed solvent containing trifluoroacetic acid (TFA), affording coumarins and quinolinones in moderate to excellent yields with more than 1000 turnover numbers (TON) to Pd. The methodology proved to tolerate a number of functional groups such as Br and CHO. On the basis of isotope experiments, a possible mechanism involving ethynyl chelation-assisted electrophilic metalation of aromatic C-H bonds by in-situ generated cationic Pd(II) species has been discussed. Also the involvement of vinylcationic species has been suggested.

  DOI：

  10.1021/jo000861q
• 作为产物：
  描述：

  2-丁炔酸 、 4-叔丁基苯酚 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到4'-tert-butylphenyl 2-butynoate
  参考文献：
  名称：

  一种新的金催化的多米诺环化反应和氧化偶联反应。

  摘要：

  DOI：

  10.1002/chem.200801848

文献信息

• Iridium(<scp>iii</scp>)-catalysed annulation of pyrazolidinones with propiolates: a facile route to pyrazolo[1,2-<i>a</i>] indazoles
  作者：Zi Yang、Zhenyu Song、Lianghua Jie、Lianhui Wang、Xiuling Cui

  DOI：10.1039/c9cc02232e

  日期：——

  A facile synthesis of various pyrazolo[1,2-a] indazoles from pyrazolidinones and propiolates via iridium(III)-catalysed C–H bond activation/subsequent [4+1] cyclization has been developed. The reaction proceeds smoothly under mild reaction conditions and propiolates act as a novel C1 synthon. This transformation represents a redox-neutral process, exhibits a highly regioselectivity, and tolerates various

  已经开发了一种通过铱（III）催化的C–H键活化/随后的[4 + 1]环化反应从吡唑啉酮和丙酸酯轻松合成各种吡唑并[1,2- a ]吲唑的方法。在温和的反应条件下，反应平稳进行，丙酸酯作为新型C 1合成子。该转变代表氧化还原中性过程，表现出高度的区域选择性，并能耐受各种官能团。
• Ruthenium(II)-Catalyzed Regioselective [3 + 2] Spiroannulation of 2<i>H</i>-Imidazoles with 2-Alkynoates
  作者：Zhenyu Song、Zi Yang、Pu Wang、Zhaojiang Shi、Tingfang Li、Xiuling Cui

  DOI：10.1021/acs.orglett.0c02024

  日期：2020.8.21

  The C═N double bond of 2H-imidazole has been employed as a C-electrophile for the ruthenium(II)-catalyzed [3 + 2] spiroannulation reaction of 4-phenyl-2H-imidazoles and 2-alkynoates to synthesize spiroimidazole-4,1′-indenes. This strategy features high regioselectivity, broad functional group tolerance, and use of ruthenium as a catalyst, providing a new method to synthesize spirocycles with potential

  2 H-咪唑的C═N双键已被用作C-亲电子试剂，用于钌（II）催化的4-苯基-2 H-咪唑和2链烷酸酯的[3 + 2]螺环合成反应，合成螺并咪唑-4，1'-茚。该策略具有高区域选择性，宽泛的官能团耐受性以及使用钌作为催化剂的特点，为合成螺环化合物提供了一种新方法，具有在药物中的潜在应用。
• Photoredox-Catalyzed Cascade Radical Cyclization of Ester Arylpropiolates with CF₃SO₂Cl To Construct 3-Trifluoromethyl Coumarin Derivatives
  作者：Long Chen、Lianlian Wu、Weijie Duan、Tao Wang、Letian Li、Keke Zhang、Jingmei Zhu、Zhi Peng、Fei Xiong

  DOI：10.1021/acs.joc.8b00581

  日期：2018.8.3

  We report a highly efficient method to construct 3-trifluoromethyl coumarins using CF3SO2Cl as the trifluoromethyl radical source with ester 3-arylpropiolates. The reaction incorporated a cascade cyclization/dearomatization/ester migration/oxidization/rearomatization process to afford various 3-trifluoromethyl coumarins under visible light irradiation in good to excellent yields.

  我们报告了一种高效的方法来构建3-三氟甲基香豆素，使用CF 3 SO 2 Cl作为带有3-芳基丙酸酯的三氟甲基自由基源。该反应结合了级联环化/脱芳香化/酯迁移/氧化/重芳香化过程，以可见光照射以良好至优异的产率提供了各种3-三氟甲基香豆素。