1,5-二环己基戊-1,4-二炔-3-酮 | 1430234-45-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,5-二环己基戊-1,4-二炔-3-酮
• 英文名称: 1,5-dicyclohexylpenta-1,4-diyn-3-one
• CAS: 1430234-45-9
• 化学式: C₁₇H₂₂O
• 分子量: 242.361
• InChiKey: BQQCBBNXZLWRSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,5-二环己基戊-1,4-二炔-3-酮 在 1,1'-双(二苯基膦)二茂铁 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 氯苯 作用下， 反应 24.5h， 以57%的产率得到1,4-dicyclohexylbuta-1,3-diyne
  参考文献：
  名称：

  Rh(I)-Catalyzed Decarbonylation of Diynones via C–C Activation: Orthogonal Synthesis of Conjugated Diynes

  摘要：

  Utilization of C-C bond activation as a unique mode of reactivity for constructing C-C bonds provides new strategies for preparing important organic molecules. Development of a Rh(I)-catalyzed C-C activation of diynones to synthesize symmetrical and unsymmetrical conjugated diynes through decarbonylation is reported. This C-C cleavage strategy takes advantage of the innate reactivity of conjugated ynones without relying on any ring strain or auxiliary directing group. This alkynation method also has orthogonal properties compared to typical cross-coupling reactions.

  DOI：

  10.1021/ol400815y
• 作为产物：
  描述：

  1,1-dibromo-2-cyclohexylethene 在 manganese(IV) oxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 1,5-二环己基戊-1,4-二炔-3-酮
  参考文献：
  名称：

  Rh(I)-Catalyzed Decarbonylation of Diynones via C–C Activation: Orthogonal Synthesis of Conjugated Diynes

  摘要：

  Utilization of C-C bond activation as a unique mode of reactivity for constructing C-C bonds provides new strategies for preparing important organic molecules. Development of a Rh(I)-catalyzed C-C activation of diynones to synthesize symmetrical and unsymmetrical conjugated diynes through decarbonylation is reported. This C-C cleavage strategy takes advantage of the innate reactivity of conjugated ynones without relying on any ring strain or auxiliary directing group. This alkynation method also has orthogonal properties compared to typical cross-coupling reactions.

  DOI：

  10.1021/ol400815y

文献信息

• Lewis acid-catalyzed chemo- and stereoselective addition of pyrroles to skipped diynones: en route to novel pyrrole-based ketocyanine dyes and alkyne-tethered enones
  作者：Marina Yu. Dvorko、Igor’ A. Ushakov、Dmitrii A. Shabalin

  DOI：10.1016/j.dyepig.2024.112293

  日期：2024.10

  and alkyne-tethered enones through Lewis acid-catalyzed addition of pyrroles to skipped diynones (penta-1,4-diyn-3-ones) are described. The protocols feature a good substrate tolerance, mild reaction conditions, and high yields of target products. A wide synthetic utility of synthesized alkyne-tethered enones as novel building blocks is demonstrated by the synthesis of diverse pyrrole-containing compounds

  描述了通过路易斯酸催化吡咯与跳过的二炔酮（五-1,4-二炔-3-酮）的路易斯酸催化加成，首次化学和立体选择性合成迄今为止未知的基于吡咯的二取代酮菁染料和炔系烯酮。该方案具有底物耐受性好、反应条件温和、目标产物收率高的特点。通过多种含吡咯化合物的合成，证明了合成的炔系烯酮作为新型结构单元的广泛合成用途。研究了新型加合物的选定代表的紫外-可见光吸收特性，以初步了解它们作为可见光诱导聚合中的光引发剂/敏化剂的潜力。