ethyl 3-(4-cyanophenyl)propiolate | 143952-58-3

• 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: ethyl 3-(4-cyanophenyl)propiolate
• 英文别名: Ethyl 3-(4-cyanophenyl)propynoate；ethyl 3-(4-cyanophenyl)prop-2-ynoate
• CAS: 143952-58-3
• 化学式: C₁₂H₉NO₂
• 分子量: 199.209
• InChiKey: IJCXWXPSKQWCBV-UHFFFAOYSA-N

物化性质

• 熔点：
  67-68 °C
• 沸点：
  336.7±25.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4-cyanophenyl)propiolate 以 四氢呋喃 、 甲醇 为溶剂， 生成 methyl (R)-(+)-5-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-3-hydroxy-1-pentanoate
  参考文献：
  名称：

  Inhibitors of cholesterol biosynthesis. 3. Tetrahydro-4-hydroxy-6-[2-(1H-pyrrol-1-yl)ethyl]-2H-pyran 2-one inhibitors of HMG-CoA reductase. 2. Effects of introducing substituents at positions three and four of the pyrrole nucleus

  摘要：

  A series of trans-tetrahydro-4-hydroxy-6-[2-(2,3,4,5-substituted-1H-pyrrol-1-yl)ethyl]-2H-pyran-2-ones and their dihydroxy acids were prepared and tested for their ability to inhibit the enzyme HMG-CoA reductase in vitro. Inhibitory potency was found to increase substantially when substituents were introduced into positions three and four of the pyrrole ring. A systematic exploration of structure-activity relationships at these two positions led to the identification of a compound ((+)-33, (+)-(4R)-trans-2-(4-fluorophenyl)-5-(1-methylethyl)-N,3-diphenyl-1-[(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-4-carboxamide) with five times the inhibitory potency of the fungal metabolite compactin.

  DOI：

  10.1021/jm00105a056
• 作为产物：
  描述：

  在 potassium tert-butylate 、 sodium amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 ethyl 3-(4-cyanophenyl)propiolate
  参考文献：
  名称：

  α-溴丙烯酸酯的制备：从醛与 Ph3P/Br3CCO2Et 合成共轭乙炔羧酸的一锅法

  摘要：

  我们已经建立了 Wittig 反应以高选择性合成 α-溴丙烯酸酯的最佳条件，并开发了一种简单高效的一锅法以中等至高收率制备各种共轭炔羧酸。

  DOI：

  10.1055/s-2008-1032070

文献信息

• Palladium-catalyzed cascade carboesterification of norbornene with alkynes
  作者：Wanqing Wu、Can Li、Jianxiao Li、Huanfeng Jiang

  DOI：10.1039/c8ob01799a

  日期：——

  An efficient and convenient palladium-catalyzed cascade carboesterification of norbornenes (NBE) with alkynes has been accomplished to afford functionalized α-methylene γ-lactone and tetrahydrofuran derivatives in good to excellent yields. This new strategy exhibits excellent atom- and step-economy, good functional group tolerance and broad substrate scope. In particular, NBE-palladium species was

  已经完成了高效且方便的降冰片烯（NBE）与炔烃的钯催化的级联碳酯化反应，从而以良好或优异的收率提供了官能化的α-亚甲基γ-内酯和四氢呋喃衍生物。这种新策略具有出色的原子和步阶经济性，良好的官能团耐受性和广泛的底物范围。特别地，提出了NBE-钯物质是催化循环中抑制β-H消除过程的关键中间体。值得注意的是，开发的协议为构建各种含氧杂环骨架提供了直接而实用的工具，说明了在合成化学和药物化学中的有希望的应用。
• Recyclable heterogeneous gold(I)-catalyzed oxidation of internal acylalkynes: Practical access to vicinal tricarbonyls
  作者：Wenli Hu、Bin Huang、Bingbo Niu、Mingzhong Cai

  DOI：10.1016/j.tetlet.2021.152953

  日期：2021.3

  A highly efficient heterogeneous gold(I)-catalyzed oxidation of internal acylalkynes has been developed using 2,6-dichloropyridine N-oxide as the oxidant in dichloromethane (CH2Cl2) at room temperature, providing a novel and practical approach for the construction of diverse vicinal tricarbonyls such as α,β-diketoesters, 1,2,3-triketones, and α,β-diketoamides in good to excellent yields. The heterogeneous

  在室温下，使用2,6-二氯吡啶N-氧化物作为二氯甲烷（CH 2 Cl 2）的氧化剂，开发了一种高效的异质金（I）催化内部酰基炔烃氧化的方法，为构建该结构提供了一种新颖而实用的方法种类繁多的邻位三羰基化合物，如α，β-二酮酸酯，1,2,3-三酮和α，β-二酮酰胺，收率良好。可以通过简单的制备方法容易地从市售试剂中获得非均相金（I）催化剂，并通过过滤反应混合物进行回收并重复使用多达七次，而不会显着降低催化效率。
• Novel palladium-catalyzed cascade carboxylative annulation to construct functionalized γ-lactones in ionic liquids
  作者：Jianxiao Li、Shaorong Yang、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/c3cc48052f

  日期：——

  A novel palladium-catalyzed, one-pot, four-step cascade method has been developed to afford functionalized gamma-lactones in moderate to good yields. This novel and general methodology represents a rare instance of carbonylation of the C(sp(3))-palladium bond.

  已经开发出新颖的钯催化的一锅四步级联方法，以中等至良好的产率提供官能化的γ-内酯。这种新颖而通用的方法代表了C（sp（3））-钯键羰基化的罕见实例。
• Transition-metal-free C–C bond cleavage and formation: efficient synthesis of 2,3-diarylimidazo[1,2-α]pyridines from 2-aminopyridines and alkynoates
  作者：Zhengwang Chen、Yuelu Wen、Guotian Luo、Min Ye、Qinghao Wang

  DOI：10.1039/c6ra19291b

  日期：——

  A highly efficient transition-metal-free cyclization reaction for the synthesis of 2,3-diarylimidazo[1,2-α]pyridines is described. A variety of substituted 2-aminopyridines and alkynoates are compatible under the standard conditions. This protocol is marked by the cleavage of a C–C bond and the formation of a new Csp2–Csp2 bond under transition-metal-free conditions.

  描述了一种高效的无过渡金属环化反应，用于合成2,3-二芳基咪唑并[1,2-α]吡啶。在标准条件下，各种取代的2-氨基吡啶和炔酸酯是相容的。该方案的特征是在无过渡金属的条件下，CC键断裂并形成新的C sp 2 -C sp 2键。
• A convenient regioselective synthesis of cyclopentadienones via palladium-catalyzed [2+2+1] cyclocarbonylation of alkynes
  作者：Yanli Xu、Jinwu Zhao、Huoji Chen、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/c3cc48308h

  日期：——

  A simple and efficient synthesis of cyclopentadienones via palladium-catalyzed cyclocarbonylation of alkynes under atmospheric pressure of carbon monoxide has been developed. The transformation was carried out under mild and ligand-free conditions, a wide range of substrates and exceptional functional group tolerance.

  已经开发了在一氧化碳的大气压下通过钯催化的炔烃环羰基化的一种简单而有效的合成环戊二烯酮的方法。转化是在温和且无配体的条件下，多种底物和出色的官能团耐受性下进行的。