3,6-bis(benzoylbiphenyl)ethynyl-9-tetradecylcarbazole | 791090-33-0

• 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: 3,6-bis(benzoylbiphenyl)ethynyl-9-tetradecylcarbazole
• 英文别名: [4-[4-[2-[6-[2-[4-(4-Benzoylphenyl)phenyl]ethynyl]-9-tetradecylcarbazol-3-yl]ethynyl]phenyl]phenyl]-phenylmethanone
• CAS: 791090-33-0
• 化学式: C₆₈H₆₁NO₂
• 分子量: 924.238
• InChiKey: SACQFQYBZPLLFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.9
• 重原子数：
  71
• 可旋转键数：
  23
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  39.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6-bis(benzoylbiphenyl)ethynyl-9-tetradecylcarbazole 在 对硝基苯酚 、 C₁₅H₃₂Ar₃MoN₃ 作用下， 以 四氯化碳 为溶剂， 反应 24.0h， 以98%的产率得到TDTC
  参考文献：
  名称：

  PREPARATION OF A CARBAZOLE-BASED MACROCYCLE VIA PRECIPITATION-DRIVEN ALKYNE METATHESIS

  摘要：

  DOI：

  10.15227/orgsyn.084.0177
• 作为产物：
  描述：

  溴代十四烷 在 哌啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 3,6-bis(benzoylbiphenyl)ethynyl-9-tetradecylcarbazole
  参考文献：
  名称：

  Arylene Ethynylene Macrocycles Prepared by Precipitation-Driven Alkyne Metathesis

  摘要：

  A convenient, multigram-scale synthesis of arylene ethynylene macrocycles near room temperature is described. Driven by the precipitation of a diarylacetylene byproduct, alkyne metathesis produces the desired macrocycles in one step from monomers in high yields.

  DOI：

  10.1021/ja046531v

文献信息

• HETEROGENEOUS ALKYNE METATHESIS
  申请人：Weissman Haim

  公开号：US20060281938A1

  公开（公告）日：2006-12-14

  The present invention provides heterogeneous organometallic catalysts for alkyne metathesis, including the metathesis of internal alkynes. Organometallic precursors are covalently bonded to the oxygen atoms of metal oxide supports to form catalysts having carbyne functionality. The heterogeneous catalysts provide improved turn-over frequencies at lower reaction temperatures than conventional catalysts.

  本发明提供了用于炔烃重排反应的异质有机金属催化剂，包括内部炔烃的重排反应。有机金属前驱体与金属氧化物支撑物的氧原子共价结合，形成具有卡宾功能的催化剂。这种异质催化剂在比传统催化剂更低的反应温度下提供了改善的周转频率。
• Synthetic Applications with Use of a Silica-Supported Alkyne Metathesis Catalyst
  作者：Hyeon Mo Cho、Haim Weissman、Jeffrey S. Moore

  DOI：10.1021/jo8003919

  日期：2008.6.1

  A highly active and durable fumed silica-supported heterogeneous molybdenum(VI) catalyst was applied to ring closing alkyne metathesis and cyclooligomerization reactions to give high yields of metathesis products near room temperature conditions.

  将高活性和耐用的气相法二氧化硅支撑的异质钼（VI）催化剂用于闭环炔烃复分解和环寡聚反应，以在室温条件下获得高产率的复分解产物。
• Arylene Ethynylene Macrocycles Prepared by Precipitation-Driven Alkyne Metathesis
  作者：Wei Zhang、Jeffrey S. Moore

  DOI：10.1021/ja046531v

  日期：2004.10.1

  A convenient, multigram-scale synthesis of arylene ethynylene macrocycles near room temperature is described. Driven by the precipitation of a diarylacetylene byproduct, alkyne metathesis produces the desired macrocycles in one step from monomers in high yields.
• A Mo(VI) Alkylidyne Complex with Polyhedral Oligomeric Silsesquioxane Ligands:  Homogeneous Analogue of a Silica-Supported Alkyne Metathesis Catalyst
  作者：Hyeon Mo Cho、Haim Weissman、Scott R. Wilson、Jeffrey S. Moore

  DOI：10.1021/ja065101x

  日期：2006.11.1

  A highly active alkyne metathesis catalyst is realized by replacing the amide ligands of a molybdenum(VI) trisamide alkylidyne complex with silanol groups from incompletely condensed POSS (polyhedral oligomeric silsesquioxane) ligands. This catalyst serves as an effective homogeneous mimic of an amorphous silica-supported catalyst. Reactivities of various catalytic mixtures are reported along with an X-ray structure of the aniline-coordinated amidodisiloxymolybdenum(VI) alkylidyne complex.
• Engineering Solid-State Morphologies in Carbazole–Ethynylene Macrocycles
  作者：Aaron D. Finke、Dustin E. Gross、Amy Han、Jeffrey S. Moore

  DOI：10.1021/ja204795q

  日期：2011.9.7

  We present a crystallographic study that systematically investigates the effects of the n-alkyl side-chain length on the crystal packing in shape-persistent macrocycles. The solid-state packing of carbazole-ethynylene-containing macrocycles is sensitive to the alkyl-chain length. In macrocycles containing n-alkyl side chains up to nine carbons in length, face-on aromatic. pi interactions predominate, while the addition of one carbon leads to a completely different packing arrangement. Macrocycles with C-10 or C-11 chains exhibit a novel packing motif wherein the alkyl chains intercalate between macrocycles, leading in one case to continuous solvent-filled channels. When crystals of the C-10 macrocycle are bathed in solvent, the included molecules exchange with the external solvent, and the alkyl chain disorder changes in response to changes in the guest volume in order to retain crystallinity. Powder X-ray diffraction data indicate that alkyl-macrocycle interactions in the longer chains "emulate" the distances typical of face-to-face pi interactions, leading to deceptive indicators of pi stacking.