3-phenyl-4-(phenylethynyl)-1H-isochromen-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 3-phenyl-4-(phenylethynyl)-1H-isochromen-1-one
• 英文别名: 3-phenyl-4-(phenylethynyl)isochromen-1-one；3-Phenyl-4-(phenylacetynyl)isocoumarin；3-phenyl-4-(phenylethynyl)isocoumarin；3-Phenyl-4-(2-phenylethynyl)isochromen-1-one
• 化学式: C₂₃H₁₄O₂
• 分子量: 322.363
• InChiKey: PQJSGOXSURVLKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene 、 3-phenyl-4-(phenylethynyl)-1H-isochromen-1-one 在 2-(4-(dipentylammonio)phenyl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到ethyl 2-(1-((tert-butyldimethylsilyl)oxy)-3-phenyl-4-(phenylethynyl)-1H-isochromen-1-yl)acetate
  参考文献：
  名称：

  甲硅烷基缩醛活化引发的级联反应合成1,2,3,4-四取代萘

  摘要：

  通过氟诱导的乳醇甲硅烷基醚的级联反应，以区域选择性的方式合成带有四个不同取代基的1,2,3,4-四取代萘，可以容易地由4-炔基异香豆素和乙烯酮甲硅烷基制备。

  DOI：

  10.1039/c6cc03510h
• 作为产物：
  描述：

  2-苯基乙炔基苯甲酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 碘 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-phenyl-4-(phenylethynyl)-1H-isochromen-1-one
  参考文献：
  名称：

  Synthesis of Isocoumarins and α-Pyrones via Electrophilic Cyclization

  摘要：

  A variety of substituted isocoumarins and alpha-pyrones are readily prepared in excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzoates and (Z)-2-alken-4-ynoates with ICI, I-2, PhSeCl, p-O2NC6H4SCl, and HI. This methodology accommodates various alkynyl esters and has been successfully extended to the synthesis of polycyclic aromatic and biaryl compounds.

  DOI：

  10.1021/jo034308v

文献信息

• Synthesis of Isocoumarins from o-Iodobenzoic Acid and Terminal Acetylenes Mediated by Palladium Complexes and Zinc Chloride
  作者：Hong-Yueh Liao、Chien-Hong Cheng

  DOI：10.1021/jo00117a023

  日期：1995.6

  o-Iodobenzoic acid (1) reacts with various terminal acetylenes (HC=CR) in the presence of Pd(PPh(3))(4), Et(3)N, and ZnCl2 in DMF to give the corresponding 3-substituted isocoumarins (C6H4COOC(R)CH: R = n-C4H9 (2a); n-C3H7 (3a); CH2OCH3 (4a); C(CH3)(2)OH (5a); CH2OH (6a); C6H5 (7a);p-CH3C6H4 (8a); 1-cyclohexenyl (9a); o-NH2C6H4 (10a)) in fair to excellent yields, In some of these catalytic reactions, substituted isocoumarin b (C6H4COOC(R)C(C=CR)) and alkylidenephthalide c were isolated in a few percent yields, Under similar conditions, treatment of 1 with a trimethylsilyl 1,3-diyne 12 led to the formation of products 3-(2-indolyl)isocoumarin (13) and an indolylphthalide 14 in a 95:5 ratio. The reaction of o-1-pentynylbenzoic acid with ZnCl2 and Et(3)N gave 3a as the sole product indicating that ZnCl2 is likely responsible for the selective formation of the six-membered isocoumarin ring, Based on this observation and the known palladium chemistry, a mechanism involving the participation of palladium complexes in the alkynylation of 1 and zinc chloride in the heteroannulation of the reaction intermediate o-1-alkynylbenzoate is proposed for the present catalytic reactions.
• Synthesis of Isocoumarins via Pd/C-Mediated Reactions of <i>o</i>-Iodobenzoic Acid with Terminal Alkynes
  作者：Venkataraman Subramanian、Venkateswara Rao Batchu、Deepak Barange、Manojit Pal

  DOI：10.1021/jo050440e

  日期：2005.6.1

  The coupling reaction of o-iodobenzoic acid with terminal alkynes by using a catalyst system of 10% Pd/C-Et3N-CuI-PPh3 has been studied in a variety of solvents. 3-Substituted isocoumarins were formed in good yields and with good regioselectivity when the reaction was performed in EtOH.
• Synthesis of isocoumarins and α-pyrones via iodocyclization
  作者：Tuanli Yao、Richard C Larock

  DOI：10.1016/s0040-4039(02)01731-8

  日期：2002.10

  A variety of 3-substituted 4-iodoisocoumarins and 6-substituted 5-iodo-2(2H)-pyranones are readily prepared in excellent yields under mild reaction conditions by the reaction of o-(l-alkynyl)benzoates and (Z)-2-alken-4-ynoates with ICI. (C) 2002 Published by Elsevier Science Ltd.
• Synthesis of Isocoumarins and α-Pyrones via Electrophilic Cyclization
  作者：Tuanli Yao、Richard C. Larock

  DOI：10.1021/jo034308v

  日期：2003.7.1

  A variety of substituted isocoumarins and alpha-pyrones are readily prepared in excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzoates and (Z)-2-alken-4-ynoates with ICI, I-2, PhSeCl, p-O2NC6H4SCl, and HI. This methodology accommodates various alkynyl esters and has been successfully extended to the synthesis of polycyclic aromatic and biaryl compounds.
• Synthesis of 1,2,3,4-tetrasubstituted naphthalenes through a cascade reaction triggered by silyl acetal activation
  作者：Hikaru Yanai、Nobuyuki Ishii、Takashi Matsumoto

  DOI：10.1039/c6cc03510h

  日期：——

  1,2,3,4-Tetrasubstituted naphthalenes bearing four different substituents were synthesized in a regioselective manner by fluoride-induced cascade reaction of lactol silyl ethers, which could be easily prepared from 4-alkynylisocoumarins and ketene silyl...

  通过氟诱导的乳醇甲硅烷基醚的级联反应，以区域选择性的方式合成带有四个不同取代基的1,2,3,4-四取代萘，可以容易地由4-炔基异香豆素和乙烯酮甲硅烷基制备。