2-acetyl-5-phenyl-2-(3-phenyl-prop-2-ynyl)-pent-4-ynoic acid ethyl ester | 95956-57-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2-acetyl-5-phenyl-2-(3-phenyl-prop-2-ynyl)-pent-4-ynoic acid ethyl ester
• 英文别名: α,α-Bis-(3-phenyl-propargyl)-acetessigsaeure-aethylester；Ethyl 2-acetyl-5-phenyl-2-(3-phenylprop-2-ynyl)pent-4-ynoate
• CAS: 95956-57-3
• 化学式: C₂₄H₂₂O₃
• 分子量: 358.437
• InChiKey: DOIVTEZLRYUBBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-acetyl-5-phenyl-2-(3-phenyl-prop-2-ynyl)-pent-4-ynoic acid ethyl ester 在 C₃₇H₃₂P₂Se₂⁽²⁺⁾*2C₃₂H₁₂BF₂₄^(1-) 作用下， 以 1,2-二氯乙烷 为溶剂， 以73 %的产率得到2-acetyl-9-phenyl-2,3-dihydro-1H-fluorene-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  通过硫族键合激活炔烃：Se⋯π相互作用催化1,6-二炔的分子内环化

  摘要：

  炔烃三键的活化主要以过渡金属为主，而有机催化剂很难在这一领域发挥有效作用。在此，我们描述了通过硫族键合对炔烃的活化，弱的Se…π相互作用能够催化1,6-二炔的分子内环化，从而为超分子催化增添了新的能力。

  DOI：

  10.1039/d3cc04096h
• 作为产物：
  描述：

  1-bromo-3-phenylprop-2-yne 生成 2-acetyl-5-phenyl-2-(3-phenyl-prop-2-ynyl)-pent-4-ynoic acid ethyl ester
  参考文献：
  名称：

  SCHULTE; REISCH; MOCK, Archiv der Pharmazie, 1962, vol. 295 /67, p. 627 - 639

  摘要：

  DOI：

文献信息

• Cp*Co(III)-Catalyzed Regioselective Synthesis of Cyclopenta[<i>b</i>]carbazoles via Dual C(sp²)–H Functionalization of 1-(Pyridin-2-yl)-indoles with Diynes
  作者：Qiuyun Li、Yanwei Wang、Bin Li、Baiquan Wang

  DOI：10.1021/acs.orglett.8b03438

  日期：2018.12.21

  Cp*Co(III)-catalyzed synthesis of cyclopenta[b]carbazoles from 1-(pyridin-2-yl)-indoles and diynes is developed. This reaction involves dual C–H activation of indoles and domino cyclizations with diynes and has excellent regioselectivity, high efficiency, a broad substrate scope, and tolerance for various functional groups. A series of cyclopenta[b]carbazole molecular scaffolds are obtained in good

  开发了Cp * Co（III）催化的1-（吡啶-2-基）-吲哚和二炔合成环戊[ b ]咔唑的方法。该反应涉及吲哚的双重C–H活化和带有二炔的多米诺环化反应，具有出色的区域选择性，高效率，广泛的底物范围以及对各种官能团的耐受性。以良好或优异的产率获得了一系列环戊[ b ]咔唑分子支架。
• Rh^III-Catalyzed Synthesis of Cyclopenta[<i>b</i>]carbazoles via Cascade C–H/C–C Bond Cleavage and Cyclization Reactions: Using Amide as a Traceless Directing Group
  作者：Yanwei Wang、Bin Li、Baiquan Wang

  DOI：10.1021/acs.orglett.9b03969

  日期：2020.1.3

  Rhodium-catalyzed cascade C-H/C-C cleavage and cyclization reactions of 3-amide substituted indoles with diynes to construct cyclopenta[b]carbazoles have been developed. A strategy amide worked as a novel traceless directing group along with C-C bond cleavage via Friedel-Crafts-retro reaction has been disclosed in this protocol. This method exhibits a broad substrate scope and tolerates various functional

  已开发出铑催化的级联CH / CC裂解和3-酰胺取代的吲哚与二炔的环化反应，以构建环戊[b]咔唑。在该方案中已公开了一种策略酰胺，它作为一种新型的无痕导向基团，以及通过Friedel-Crafts-retro反应的CC键裂解。该方法显示出广泛的底物范围并耐受各种官能团，从而以良好或高收率提供了咔唑衍生物。
• Fused Phenanthridines: Domino Cyclization of 1,6-Diynes with Bromo(iso)quinoline
  作者：Yimin Hu、Yongjie Sun、Jiping Hu、Tao Zhu、Tao Yu、Quansheng Zhao

  DOI：10.1002/asia.201000692

  日期：2011.3.1

  An offer you can′t re‐fused: The first examples of a convenient domino synthesis of 7,11‐diphenyl‐9,10‐dihydro‐8H‐cyclopentaphenanthridine derivatives, such as 3, by the domino palladium‐catalyzed cyclization reactions of simple 1,6‐diynes with bromo(iso)quinoline in a single operation are described.

  您不能拒绝的报价：通过多米诺骨牌钯催化的环戊基环化反应方便地多米诺骨牌合成7,3,11-二苯基-9,10-二氢-8 H-环戊苯二胍衍生物（例如3）的第一个示例描述了在单个操作中简单的1,6-二炔与溴（异）喹啉的混合物。
• Efficient Activation of Aromatic CH Bonds for Fused Polyaromatic Hydrocarbon Construction
  作者：Yimin Hu、Hao Yao、Yongjie Sun、Jing Wan、Xiangang Lin、Tao Zhu

  DOI：10.1002/chem.201000672

  日期：2010.7.5

  An extraordinary domino method for the construction of polycyclic aromatic hydrocarbons has been established. Various 4,9‐diphenyl‐2,3‐dihydro‐1H‐cyclopenta[b]naphthalene derivatives are constructed by the palladium(0)‐catalyzed reaction of diynes with aryl halides through C–C coupling and CH bond activation of the incorporated aryl group, which provides an effective π‐system synthesis.

  已经建立了用于构造多环芳族烃的非同寻常的多米诺骨牌方法。各种4,9-二苯基-2,3-二氢- 1 ħ环戊二烯并[ b ]萘衍生物是由钯构成（0）至C-C偶联和C与芳基卤化物的二炔催化的反应 H键活化的结合的芳基，可提供有效的π系统合成。
• Gold-Catalyzed Intramolecular [3 + 2]-Cycloaddition of Arenyne-Yne Functionalities
  作者：Jian-Jou Lian、Po-Chiang Chen、Yau-Ping Lin、Hao-Chun Ting、Rai-Shung Liu

  DOI：10.1021/ja0643826

  日期：2006.9.1

  We report a new efficient intramolecular [3 + 2]-cycloaddition of unactivated arenyne (or enyne)-yne functionalities, catalyzed mainly by the AuPPh3SbF6 complex (2 mol %) under ambient conditions. The value of this cyclization is reflected by its applicability to a wide range of diyne substrates bearing various functional groups.