cinnamyl 3-phenylpropiolate | 10568-27-1

• 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: cinnamyl 3-phenylpropiolate
• 英文别名: [(E)-3-phenylprop-2-enyl] 3-phenylprop-2-ynoate
• CAS: 10568-27-1
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: MPDBOVDVJJJCMO-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cinnamyl 3-phenylpropiolate 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以80%的产率得到(E)-pent-1-en-4-yne-1,5-diyldibenzene
  参考文献：
  名称：

  Catalytic Decarboxylative sp−sp³ Coupling

  摘要：

  A palladium-catalyzed 1,4-enyne synthesis was developed based the decarboxylative coupling of acetylides with allyl electrophiles. Stereochemical studies have implicated palladium-allyl-acetylides as intermediates. Thus, decarboxylative metalation was established as an environmentally benign alternative to transmetalation from alkynyl tin reagents.

  DOI：

  10.1021/ja0542688
• 作为产物：
  描述：

  phenylpropiolyl chloride 生成 cinnamyl 3-phenylpropiolate
  参考文献：
  名称：

  STEVENSON, ROBERT;WEBER, JAMES V., J. NATUR. PROD., 52,(1989) N, C. 367-375

  摘要：

  DOI：

文献信息

• Selective Alkynylallylation of the C−C σ Bond of Cyclopropenes
  作者：Zeqi Jiang、Sheng‐Li Niu、Qiang Zeng、Qin Ouyang、Ying‐Chun Chen、Qing Xiao

  DOI：10.1002/ange.202008886

  日期：2021.1.4

  bond scission with conjunctive cross‐couplings, this decarboxylative reorganization reaction features fascinating atom and step economy and provides an efficient approach to highly functionalized dienynes from readily available substrates. Without further optimization, gram‐scale products can be easily obtained by such a simple, neutral, and low‐cost catalytic system with high TONs. DFT calculations

  摘要使用丙炔酸烯丙酯作为烯丙基化和炔基化试剂，首次实现了环丙烯中特定 C−C σ 键的 Pd 催化区域和立体选择性炔基烯丙基化。通过合并选择性 C(sp2)-C(sp3）键断裂与连接交叉偶联，这种脱羧重组反应具有令人着迷的原子和步骤经济性，并提供了一种从容易获得的底物中制备高度官能化二烯的有效方法。无需进一步优化，通过这种简单、中性、低成本的高TON催化系统就可以轻松获得克级产品。DFT 计算为产物的形成提供了理论依据，并表明环丙烯双键选择性插入双齿 Pd 配合物的 C-Pd 键中，以及随后由 1,4-钯迁移促进的非经典 β-C 消除是对于反应的成功至关重要。
• Cu(I)-Catalyzed Carboxylative Coupling of Terminal Alkynes, Allylic Chlorides, and CO₂
  作者：Wen-Zhen Zhang、Wen-Jie Li、Xiao Zhang、Hui Zhou、Xiao-Bing Lu

  DOI：10.1021/ol102172v

  日期：2010.11.5

  A highly selective synthesis of a variety of functionalized allylic 2-alkynoates was realized via the carboxylative coupling of terminal alkynes, allylic chlorides, and CO2 catalyzed by the N-heterocyclic carbene copper(I) complex (IPr)CuCl. The catalyst can be easily recovered without any loss in activity and product selectivity.

  通过N-杂环卡宾铜（I）配合物（IPr）CuCl催化的末端炔烃，烯丙基氯化物和CO 2的羧基偶联，实现了多种官能化烯丙基2-链烷酸酯的高度选择性合成。可以容易地回收催化剂，而没有任何活性和产物选择性的损失。
• Single Cu(I)-Photosensitizer Enabling Combination of Energy-Transfer and Photoredox Catalysis for the Synthesis of Benzo[<i>b</i>]fluorenols from 1,6-Enynes
  作者：Limeng Zheng、Han Xue、Bingwei Zhou、Shu-Ping Luo、Hongwei Jin、Yunkui Liu

  DOI：10.1021/acs.orglett.1c01427

  日期：2021.6.4

  An efficient, mild, and atom-economical synthesis of benzo[b]fluorenols from 1,6-enynes has been developed under photocatalytic conditions. A single P/N heteroleptic Cu(I)-photosensitizer might exhibit both energy-transfer and photoredox catalytic activities in the formation of benzo[b]fluorenols.

  已经在光催化条件下开发了一种从 1,6-烯炔有效、温和且原子经济地合成苯并 [ b ] 芴醇的方法。单个 P/N 杂配 Cu(I)-光敏剂可能在苯并 [ b ] 芴醇的形成过程中表现出能量转移和光氧化还原催化活性。
• Palladium-Catalyzed Decarboxylative Coupling of Allylic Alkynoates with Arynes
  作者：Shao-Feng Pi、Bo-Xiao Tang、Jin-Heng Li、Yi-Lin Liu、Yun Liang

  DOI：10.1021/ol900643r

  日期：2009.6.4

  A novel and selective protocol for the synthesis of 1-allyl-2-ethynylbenzenes has been developed by palladium-catalyzed decarboxylative coupling of allylic alkynoates with arynes. This new route allows for both sp−sp2 and sp2−sp3 couplings of allylic alkynoates with arynes in one pot involving a decarboxylation process.

  通过钯催化烯丙基炔酸与芳烃的脱羧偶联，已经开发出一种新颖且选择性的方案，用于合成1-烯丙基-2-乙炔基苯。这一新途径允许在一个罐中将烯丙基炔酸酯与芳烃的sp-sp 2和sp 2 -sp 3偶联，涉及脱羧过程。
• A Palladium-Catalyzed Cyclization−Oxidation Sequence:  Synthesis of Bicyclo[3.1.0]hexanes and Evidence for S_N2 C−O Bond Formation
  作者：Xiaofeng Tong、Matthias Beller、Man Kin Tse

  DOI：10.1021/ja070919j

  日期：2007.4.1

  A novel palladium-catalyzed cyclization−oxidation sequence yielding bicyclo[3.1.0]hexanes was developed. A mechanism involving a Pd(II)/Pd(IV) cycle was proposed. An SN2 C−O bond formation from an alkyl−palladium(IV) intermediate was also suggested.

  开发了一种新的钯催化环化氧化序列，产生双环 [3.1.0] 己烷。提出了涉及 Pd(II)/Pd(IV) 循环的机制。还建议从烷基-钯（IV）中间体形成 SN2 CO 键。