1,5-dimesitylpenta-1,4-diyn-3-one | 51118-05-9

• 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: 1,5-dimesitylpenta-1,4-diyn-3-one
• 英文别名: 1,5-Dimesityl-penta-1,4-diin-3-on；1,4-Pentadiyn-3-one, 1,5-bis(2,4,6-trimethylphenyl)-；1,5-bis(2,4,6-trimethylphenyl)penta-1,4-diyn-3-one
• CAS: 51118-05-9
• 化学式: C₂₃H₂₂O
• 分子量: 314.427
• InChiKey: XTHJKNXKQMUYOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  1,5-dimesitylpenta-1,4-diyn-3-one 在 Wilkinson's catalyst 作用下， 生成 1,4-dimesitylbuta-1,3-diyne
  参考文献：
  名称：

  Mueller,E.; Segnitz,A., Justus Liebigs Annalen der Chemie, 1973, p. 1583 - 1591

  摘要：

  DOI：
• 作为产物：
  描述：

  (2,2-二溴乙烯基)-2,4,6-三甲基苯 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-dimesitylpenta-1,4-diyn-3-one
  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

• Mueller,E.; Segnitz,A., Justus Liebigs Annalen der Chemie, 1973, p. 1583 - 1591
  作者：Mueller,E.、Segnitz,A.

  DOI：——

  日期：——
• Chauvelier; Bardone, Bulletin de la Societe Chimique de France, 1952, p. 386
  作者：Chauvelier、Bardone

  DOI：——

  日期：——
• Rh(I)-Catalyzed Decarbonylation of Diynones via C–C Activation: Orthogonal Synthesis of Conjugated Diynes
  作者：Alpay Dermenci、Rachel E. Whittaker、Guangbin Dong

  DOI：10.1021/ol400815y

  日期：2013.5.3

  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.