Benzoyldiacetylen | 29743-36-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoyldiacetylen
• 英文别名: 1-Phenyl-2,4-pentadiyn-1-one；1-phenylpenta-2,4-diyn-1-one
• CAS: 29743-36-0
• 化学式: C₁₁H₆O
• 分子量: 154.168
• InChiKey: ZKQQJUBGJLUJNT-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  106°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Benzoyldiacetylen 在 四甲基乙二胺 、 氧气 、 copper(l) chloride 作用下， 生成 1,10-Diphenyldeca-2,4,6,8-tetrain-1,10-dion
  参考文献：
  名称：

  双（三甲基甲硅烷基）聚炔与酰基氯的Friedel-crafts反应；末端炔基酮的有用途径

  摘要：

  双（三甲基甲硅烷基）乙炔Me 3 Si（CC）n SiMe 3与酰氯-氯化铝络合物XC 6 H 4 COCl·AlCl 3在二氯甲烷中于0-20°反应形成相应的酮XC 6 H 4 CO（CC）n SiMe 3具有极好（n = 1）或中等（n = 2，4）的产率。用含水甲醇硼砂处理产品实际上可定量释放末端炔基酮XC 6 H 4 CO（CC）nH.该方法提供了通向酮四炔的第一种实用途径（n＝ 4），并有用地补充了现有的用于酮-单炔和-二炔合成的氧化方法。与我草酰氯氯化-铝复合发生反应3 SiCCSiMe 3，得到新的甲硅烷基取代的杂环（I）：

  DOI：

  10.1016/s0022-328x(00)89260-8
• 作为产物：
  描述：

  苯甲酰氯 在 aluminum (III) chloride 、 potassium fluoride 、 18-冠醚-6 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 Benzoyldiacetylen
  参考文献：
  名称：

  晶体堆积和亲金相互作用对芳酰基乙炔化物-金（I）配合物的多晶型物和溶剂化物的发光性质的影响。

  摘要：

  研究了（ArCOC≡C）n AuPEt3（n = 1,2）类型的金（I）乙炔化金络合物的化学取代，晶体堆积和亲金相互作用对其发光性能的影响。所有描述的复合物在溶液中经历配体加扰，导致形成稳定的，易于分离的晶体，其中包含[ArCO（C≡C）n] 2 Au-（Et3 P）2 Au +均质物质。特别是，我们观察到（苯甲酰乙炔化物）金（I）络合物可产生三种具有显着不同的发光特性的晶体形式。我们监测了这些形式的转化途径：干燥后的均绿络合物的橙色发光形式自发转变为亮绿色荧光形式，最后转变为弱蓝色发光形式。此外，我们报告了一个罕见的Au·Au·Au链螺旋排列的例子，这是在杂配的（苯甲酰基乙炔）金（I）络合物的情况下首次在乙炔金（I）络合物中观察到的。这是非常罕见的情况，其中可以直接比较杂配剂和AuI配合物的晶体结构和随后的电子性质。

  DOI：

  10.1002/chem.201901101

文献信息

• Addition of secondary amines to diacetylenic ketones
  作者：R. Mestres

  DOI：10.1039/p19720000805

  日期：——

  Secondary amines add across the free ethynyl group of unsubstituted diacetylenic ketones. Reactions of piperidine with 1-phenylhexa-2,4-diyn-1-one (7), a methyl-substituted derivative, afford 1-phenyl-5-piperidinohex-4-en-2-yn-1-one (17), 3,5-dipiperidinobiphenyl (20), and a diadduct (21); in the presence of water 1-phenyl-3-piperidino-hex-2-ene-1,5-dione (27) is also obtained. Strong solvent-induced

  仲胺跨未取代的二炔酮的游离乙炔基加成。哌啶与甲基取代的衍生物1-苯基六-2,4-二炔-1-酮（7）的反应，得到1-苯基-5-哌啶子酮-4-en-2-yn-1-酮（17） ，3,5-二哌啶子基联苯（20）和二加合物（21）; 在水存在下，也获得了1-苯基-3-哌啶子基-己-2-烯-1，5-二酮（27）。在加合物的紫外光谱中观察到了高达40 nm的强溶剂诱导的位移。已经获得了一些不稳定的烷基二炔酮[[4] –（6）]。
• Synthesis of 4-Pyrones by Formal Hydration of 1,3-Diynones Promoted by 1,4-Addition of Piperidine
  作者：Erandi Liyanage Perera、Daesung Lee

  DOI：10.1021/acs.orglett.2c02914

  日期：2022.9.30

  A new approach for the synthesis of 4-pyrones with broader substrate scope and functional group tolerance is described. The reaction proceeds via an initial 1,4-addition by piperidine, followed by nitrogen-assisted 6-endo-dig cyclization and hydrolysis. 1,3-Diynones with nonenolizable electron-withdrawing ketones and nonpropargylic H provide relatively high yields. For substrates with particular R2

  描述了一种合成具有更广泛底物范围和官能团耐受性的 4-吡喃酮的新方法。该反应通过哌啶的初始 1,4-加成，然后是氮辅助 6 -endo-dig环化和水解进行。具有非烯醇化吸电子酮和非炔丙基 H 的 1,3-二炔酮提供相对较高的产率。对于具有特定 R 2取代基的底物，分离出 1,4- 或 1,6-加合物，这表明 R 2取代基的空间和电子因素应该对 6 -endo-dig环化产生强烈影响。
• Bohlmann,F. et al., Chemische Berichte, 1963, vol. 96, p. 226 - 236
  作者：Bohlmann,F. et al.

  DOI：——

  日期：——
• Regioselective Trapping of Terminal Di-, Tri-, and Tetraynes with Benzyl Azide
  作者：Thanh Luu、Robert McDonald、Rik R. Tykwinski

  DOI：10.1021/ol062522a

  日期：2006.12.1

  The reaction of benzyl azide with terminal di-, tri-, and tetraynes appended with a range of functional groups has been explored. Standard reaction conditions for BnN3 catalyzed by CuSO(4)(.)5H(2)O gave alkynyl, butadiynyl, and hexatriynyl triazoles in moderate to good yields. The reaction proceeds regioselectively as determined by the X-ray crystallographic analysis of three derivatives (1c, 1d, and 3c), and no evidence of multiple azide addition to the polyyne framework is observed.
• Inhibition of Pseudomonas aeruginosa quorum sensing by chemical induction of the MexEF-oprN efflux pump
  作者：Rasmus Kristensen、Jens Bo Andersen、Morten Rybtke、Charlotte Uldahl Jansen、Blaine Gabriel Fritz、Rikke Overgaard Kiilerich、Jesper Uhd、Thomas Bjarnsholt、Katrine Qvortrup、Tim Tolker-Nielsen、Michael Givskov、Tim Holm Jakobsen

  DOI：10.1128/aac.01387-23

  日期：2024.2.7

  ABSTRACT The cell-to-cell communication system quorum sensing (QS), used by various pathogenic bacteria to synchronize gene expression and increase host invasion potentials, is studied as a potential target for persistent infection control. To search for novel molecules targeting the QS system in the Gram-negative opportunistic pathogen Pseudomonas aeruginosa , a chemical library consisting of 3,280 small compounds from LifeArc was screened. A series of 10 conjugated phenones that have not previously been reported to target bacteria were identified as inhibitors of QS in P. aeruginosa . Two lead compounds (ethylthio enynone and propylthio enynone) were re-synthesized for verification of activity and further elucidation of the mode of action. The isomeric pure Z-ethylthio enynone was used for RNA sequencing, revealing a strong inhibitor of QS-regulated genes, and the QS-regulated virulence factors rhamnolipid and pyocyanin were significantly decreased by treatment with the compounds. A transposon mutagenesis screen performed in a newly constructed lasB-gfp monitor strain identified the target of Z-ethylthio enynone in P. aeruginosa to be the MexEF-OprN efflux pump, which was further established using defined mex knockout mutants. Our data indicate that the QS inhibitory capabilities of Z-ethylthio enynone were caused by the drainage of intracellular signal molecules as a response to chemical-induced stimulation of the MexEF-oprN efflux pump, thereby inhibiting the autogenerated positive feedback and its enhanced signal-molecule synthesis.