1-(4-methoxyphenyl)-4-phenylbut-3-yn-2-one | 99805-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxyphenyl)-4-phenylbut-3-yn-2-one
• CAS: 99805-40-0
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: BFJATBRDXLDYNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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-(4-methoxyphenyl)-4-phenylbut-3-yn-2-one 在 tin(II) chloride dihdyrate 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 4-phenylspiro[4.5]deca-3,6,9-triene-2,8-dione
  参考文献：
  名称：

  Dearomatisation approaches to spirocyclic dienones via the electrophilic activation of alkynes

  摘要：

  描述了两种简单的金属介导的去芳构螺环化方法，可以从茴香醚和酚-烯酮中生成高产率的螺环烯酮。

  DOI：

  10.1039/c6ob02426b
• 作为产物：
  描述：

  4-甲氧基苯乙醛 在 正丁基锂 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 1-(4-methoxyphenyl)-4-phenylbut-3-yn-2-one
  参考文献：
  名称：

  Synthesis of Spiro[4.5]trienones by Intramolecular ipso-Halocyclization of 4-(p-Methoxyaryl)-1-alkynes

  摘要：

  A wide variety of 3-halospiro[4.5]trienones are readily prepared in good to excellent yields by the intramolecular ipso-halocyclization of 4-(p-methoxyaryl)-1-alkynes under mild reaction conditions. ICl, I2, and Br2 are all effective electrophiles for this process under carefully optimized reaction conditions.

  DOI：

  10.1021/ja053079m

文献信息

• Enantioselective Addition of Alkynyl Ketones to Nitroolefins Assisted by Brønsted Base/H‐Bonding Catalysis
  作者：Teresa E. Campano、Igor Iriarte、Olatz Olaizola、Julen Etxabe、Antonia Mielgo、Iñaki Ganboa、José M. Odriozola、Jesús M. García、Mikel Oiarbide、Claudio Palomo

  DOI：10.1002/chem.201805542

  日期：2019.3.21

  sets of enolizable alkynyl ketones (including methyl ynones with α‐aryl, α‐alkenyl, and α‐alkoxy groups) were able to react smoothly with nitroolefins with the assistance of bifunctional Brønsted base/H‐bond catalysts to provide adducts with two consecutive tertiary stereocenters in a highly diastereo‐ and enantioselective fashion. Further transformation of the obtained adducts into optically active acyclic

  在双功能布朗斯台德碱/氢键催化剂的辅助下，各种可烯化的炔基酮（包括带有α-芳基，α-烯基和α-烷氧基的甲基炔酮）能够与硝基烯烃平稳反应，从而提供两个连续的加合物高度非对映和对映选择性的三级立体中心。还证明了所获得的加合物进一步转化为旋光性无环和多环分子，包括一些具有复杂碳骨架的分子。
• Catalytic Asymmetric Conjugate Addition/Hydroalkoxylation Sequence: Expeditious Access to Enantioenriched Eight-Membered Cyclic Ether Derivatives
  作者：Suo-Suo Qi、Hao Yin、Yi-Feng Wang、Chao-Jie Wang、Hong-Te Han、Tong-Tong Man、Dan-Qian Xu

  DOI：10.1021/acs.orglett.1c00392

  日期：2021.4.2

  developed. A variety of eight-membered cyclic ethers with two contiguous tertiary stereocenters were obtained in high yields with excellent stereoselectivities. This reaction not only provides a new strategy for constructing enantioenriched eight-membered cyclic ethers but also demonstrates the practicability of ynones as C4-syntons for the synthesis of chiral medium-membered rings.

  通过结合双功能方酰胺和DBU催化，在原位生成的邻喹啉甲烷和ynones之间开发了顺序对映选择性共轭加成/氢烷氧基化反应。具有高产率和优异的立体选择性，获得了具有两个连续的叔立体中心的各种八元环醚。该反应不仅为构建对映体富集的八元环醚提供了新的策略，而且证明了炔酮作为C4-合成子用于合成手性中元环的实用性。
• Palladium-catalyzed carbonylative coupling of (chloromethyl)arenes with terminal arylalkynes to produce 1,4-diaryl-3-butyn-2-ones
  作者：Xiujuan Feng、Jiliang Song、Hesong Liu、Liangguang Wang、Xiaoqiang Yu、Ming Bao

  DOI：10.1039/c3ra42972e

  日期：——

  A convenient and efficient method for the synthesis of 1,4-diaryl-3-butyn-2-ones is described. The carbonylative coupling reactions of (chloromethyl)arenes with terminal arylalkynes proceeded smoothly in the presence of a PdCl2(PPh3)2 catalyst under mild reaction conditions to produce the corresponding 1,4-diaryl-3-butyn-2-ones in satisfactory to excellent yields.

  描述了一种方便高效的1,4-二苯基-3-丁炔-2-酮的合成方法。在温和反应条件下，(氯甲基)芳烃与末端芳基炔烃的碳基耦合反应在PdCl2(PPh3)2催化剂的作用下顺利进行，产出了相应的1,4-二苯基-3-丁炔-2-酮，得率令人满意至优秀。
• Alkylation/Ipso-cyclization of Active Alkynes Leading to 3-Alkylated Aza- and Oxa-spiro[4,5]-trienones
  作者：Pu Chen、Jian-Hong Fan、Wen-Qin Yu、Bi-Quan Xiong、Yu Liu、Ke-Wen Tang、Jun Xie

  DOI：10.1021/acs.joc.1c03118

  日期：2022.5.6

  spiro[4.5]trienones via alkylation/ipso-cyclization of activated alkynes with 4-alkyl-DHPs under transition-metal-free conditions is proposed. This alkylation successively undergoes the generation of alkyl radicals, addition of alkyl radicals to the alkynes, and intramolecular ipso-cyclization. The mechanism studies suggest that the alkylation/ipso-cyclization involves a radical process. This ipso-cyclization

  提出了一种在无过渡金属条件下通过活化炔烃与 4-烷基-DHP 的烷基化/同环化制备3-烷基化螺[4.5]三烯酮的方法。这种烷基化依次经历烷基自由基的产生、烷基自由基与炔烃的加成以及分子内的同位环化。机理研究表明烷基化/同环化涉及一个自由基过程。这种同环化过程显示出一系列优点，例如可访问性、条件温和、效率高、安全性更高和环境友好的方法。
• Visible Light Assisted Selenylative Intramolecular Dearomative Carbo-Spirocyclisation (IDCS) of Homologated-Ynones
  作者：Sushree Ranjan Sahoo、Biswajit Das、Debayan Sarkar、F. Henkel、H. Reuter

  DOI：10.1002/ejoc.201901821

  日期：2020.2.21

  A straightforward synthesis of selenylative carbo‐spirocyclisation from homologated‐ynones is presented trough visible light assisted intramolecular dearomatization. In the process, the substituted spiro‐triene‐2,8‐dione was readily transformed into various spiro‐cycles and substituted 2‐naphthols.

  通过可见光辅助的分子内脱芳香化作用，从同源的炔酮直接合成硒化碳-螺环化反应。在此过程中，取代的螺-三烯-2,8-二酮很容易转化为各种螺环和取代的2-萘酚。