4-oxo-6-phenylhex-5-ynoic acid | 14901-29-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 4-oxo-6-phenylhex-5-ynoic acid
• 英文别名: 4-Oxo-6-phenyl-5-hexynoic acid
• CAS: 14901-29-2
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: VRUVCRQSUNRWAO-UHFFFAOYSA-N

物化性质

• 熔点：
  80 °C
• 沸点：
  404.2±28.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-oxo-6-phenylhex-5-ynoic acid 在 [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)₂]Cl 、 potassium tert-butylate 、 1-叠氮基-1,2-苯并氧代-3(1h)-酮 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 18.5h， 生成 5-(azidomethyl)-5-(phenylethynyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  使用高价碘试剂从烯烃对（1,1）和（1,2）-叠氮内酯的不同访问

  摘要：

  通过将羧酸叠氮化和环化到烯烃上，已开发了一种通用的叠氮内酯合成方法。基于光氧化还原或钯催化，可以选择性地合成（1,1）和（1,2）叠氮基内酯。选择催化剂和用作叠氮化物源的苯并齐多醇试剂对于引发自由基或路易斯酸介导的过程具有不同的结果至关重要。这些转化是在温和的条件下使用低催化剂负载量进行的，并获得了大范围的叠氮基内酯。

  DOI：

  10.1002/chem.201702599
• 作为产物：
  描述：

  4-oxo-4-(2-phenylethynyl)-1-butanol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 0.05h， 以90%的产率得到4-oxo-6-phenylhex-5-ynoic acid
  参考文献：
  名称：

  An efficient Synthesis of Acetylenic ?- and ?-Hydroxy Ketones, ?- and ?-keto acids, and ?- diketones via addition of 1-alkinyllithium compounds to ?- and ?-lactones

  摘要：

  2-Hydroxy-6-alkyn-5-ones 3, 1-hydroxy-5-alkyn-4-ones 4, and 1-hydroxy-6-alkyn-5-ones 5 are conveniently obtained in exellent yields through a highly selective monoaddition of an 1-alkynyllithium compound 2 to gamma-valerolactone (1 a), gamma-butyrolactone (1 b) or delta-valerolactone (1 c). They are oxidized by pyridinium dichromate or Jones reagent to the corresponding acetylenic 1,4-diketones 6, 4-oxo carboxylic acids 7, and 5-oxo carboxylic acids 8, respectively.

  DOI：

  10.1002/prac.19933350503

文献信息

• (HMe2SiCH2)2: A Useful Reagent for B(C6F5)3-Catalyzed Reduction–Lactonization of Keto Acids: Concise Syntheses of (–)-cis-Whisky and (–)-cis-Cognac Lactones
  作者：Zhenlei Song、Hengmu Xie、Ji Lu、Yingying Gui、Lu Gao

  DOI：10.1055/s-0036-1588488

  日期：2017.11

  (HMe2SiCH2)2 has been utilized as a useful reagent for B(C6F5)3-catalyzed reduction–lactonization of keto acids to synthesize γ- and δ-lactones. The process led concisely to (–)-cis-whisky and (–)-cis-cognac lactones in respective overall yields of 32% and 36%.

  (HMe2SiCH2)2 已被用作 B(C6F5)3 催化的酮酸还原-内酯化合成γ-和δ-内酯的有用试剂。该过程简明地导致 (-)-cis-whisky 和 ​​(-)-cis-cognac 内酯的总产率分别为 32% 和 36%。
• Catalytic Ynone–Amidine Formal [4 + 2]-Cycloaddition for the Regioselective Synthesis of Tricyclic Azepines
  作者：T. Prabhakar Reddy、Jagjeet Gujral、Pritam Roy、Dhevalapally B. Ramachary

  DOI：10.1021/acs.orglett.0c03711

  日期：2020.12.18

  A Ca(OTf)2- and self-promoted ynone–amidine atom-economic formal [4 + 2]-cycloaddition of various ynones with amidines is reported for the construction of highly functionalized tricyclic azepines. High reaction rate, ease of operation, and high product selectivity with wide substrate scope are the key advantages of the present annulation protocol.

  报道了一种由Ca（OTf）2-和自我促进的ynone-am原子-经济形式的各种ynone与的正式[4 + 2]-环加成反应，用于构建高度官能化的三环a庚因。高反应速率，易于操作以及在宽范围的基板范围内的高产品选择性是本环法协议的主要优势。
• Regioselective synthesis of oxepinones and azepinones by gold-catalyzed cycloisomerization of functionalyzed cyclopropyl alkynes
  作者：Jesús M. Fernández-García、Patricia García-García、Manuel A. Fernández-Rodríguez、Alexandra Pérez-Anes、Enrique Aguilar

  DOI：10.1039/c3cc46238b

  日期：——

  A regioselective synthesis of oxepinones and azepinones in good to excellent yields from alkynylcyclopropanecarboxylic acid derivatives is described. This novel cycloisomerization cascade process consists of a nucleophilic addition followed by a cyclopropane ring-opening, where both donor and acceptor groups are required as substituents of the cyclopropane ring.

  本研究介绍了一种以炔基环丙烷羧酸衍生物为原料，以良好到极佳收率的区域选择性合成氧杂环庚酮和氮杂环庚酮的方法。这种新型的环异构化级联过程包括亲核加成和环丙烷开环，其中供体和受体基团都需要作为环丙烷环的取代基。
• Process for arylamine production
  申请人：Goodbrand Bruce H.

  公开号：US20060111582A1

  公开（公告）日：2006-05-25

  4-aminobiphenyl derivative arylamine compounds are formed by providing an iodinated organic compound; substituting the iodinated organic compound at carboxylic acid groups thereof to provide ester protecting groups; conducting an Ullman condensation reaction to convert the product of step (ii) into an arylamine compound; and conducting a Suzuki coupling reaction to add an additional phenyl group to the arylamine compound in the 4-position relative to the nitrogen.

  通过提供碘代有机化合物来形成4-氨基联苯衍生物芳胺化合物；用羧酸基取代碘代有机化合物以提供酯保护基；进行乌尔曼缩合反应将步骤（ii）的产物转化为芳胺化合物；并进行铃木偶联反应，在与氮相对的4位上向芳胺化合物中添加额外的苯基。
• Trichloromethylative Olefin Lactonization by Photoredox Catalysis
  作者：Shinji Harada、Ryotaro Koyama、Ryuya Masuda、Shigeru Arai

  DOI：10.1002/ejoc.202300747

  日期：2023.10.9

  Trichloromethylative olefin lactonization was reported. A photoredox iridium catalyst irradiated with blue LEDs promoted the reaction without using hazardous reagents. The mechanistic studies were performed by experimental and theoretical means. The trichloromethyl moiety of the product could be converted to the corresponding dichloroalkene and chloroalkyne in addition to the carboxyl group.

  报道了三氯甲基化烯烃内酯化。用蓝色 LED 照射的光氧化还原铱催化剂在不使用危险试剂的情况下促进了反应。通过实验和理论手段进行了机理研究。除羧基外，产物的三氯甲基部分还可转化为相应的二氯烯烃和氯炔。