ethyl 1-trans-cinnamyl-2-oxocyclopentanecarboxylate | 112825-94-2

• 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 1-trans-cinnamyl-2-oxocyclopentanecarboxylate
• 英文别名: ethyl 2-oxo-1-(3-phenyl-2-propen-1-yl)-1-cyclopentanecarboxylate；2-ethoxycarbonyl-2-<(E)-3-phenyl-2-propenyl>cyclopentanone；ethyl 1-cinnamyl-2-oxocyclopentanecarboxylate；ethyl 1-((E)-3-phenylallyl)-2-oxocyclopentanecarboxylate；(+/-)-1-trans-cinnamyl-2-oxo-cyclopentanecarboxylic acid ethyl ester；(+/-)-1-trans-Cinnamyl-2-oxo-cyclopentancarbonsaeure-aethylester；ethyl 2-oxo-1-[(E)-3-phenylprop-2-enyl]cyclopentane-1-carboxylate
• CAS: 112825-94-2
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: QRCDPXDQSIGVJP-UXBLZVDNSA-N

物化性质

• 沸点：
  392.6±35.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  ethyl 1-trans-cinnamyl-2-oxocyclopentanecarboxylate 在 barium dihydroxide 、 sodium hydroxide 作用下， 生成 2-cinnamylcyclopentan-1-one
  参考文献：
  名称：

  Treibs et al., Chemische Berichte, 1954, vol. 87, p. 356,362

  摘要：

  DOI：
• 作为产物：
  描述：

  Sodium; 2-ethoxycarbonyl-cyclopent-1-enolate 、 Cinnamyl bromide 生成 ethyl 1-trans-cinnamyl-2-oxocyclopentanecarboxylate
  参考文献：
  名称：

  Treibs et al., Chemische Berichte, 1954, vol. 87, p. 356,362

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Allylation of Pronucleophiles with Alkynes at 50 °C – Remarkable Effect of 2-(Dicyclohexylphosphanyl)-2′-(dimethylamino)biphenyl as Ligand
  作者：Nitin T. Patil、Dschun Song、Yoshinori Yamamoto

  DOI：10.1002/ejoc.200600337

  日期：2006.9

  The allylation of various pronucleophiles 1a–i with 1-phenylprop-1-yne (2) proceeded very smoothly at 50 °C in the presence of catalytic amounts of Pd2(dba)3·CHCl3 (5 mol-%) and 2-(dicyclohexylphosphanyl)-2′-(dimethylamino)biphenyl (I; 20 mol-%) in toluene, whilst when Pd(PPh3)4 or Pd2(dba)3·CHCl3/PPh3 were used, the reaction needed 100 °C for completion.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  在催化量的 Pd2(dba)3·CHCl3 (5 mol-%) 和 2-(二环己基膦酰基)-2'-(二甲氨基)联苯 (I; 20 mol-%) 在甲苯中，而当使用 Pd(PPh3)4 或 Pd2(dba)3·CHCl3/PPh3 时，反应需要 100 °C 才能完成。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Hexacarbonylmolybdenum(0)-Induced Dechalcogenization of Allylic Sulfides, Sulfones, and Selenides: Nucleophilic Substitution and Reductive Dechalcogenization
  作者：Yoshiro Masuyama、Kohji Yamada、Soh-hei Shimizu、Yasuhiko Kurusu

  DOI：10.1246/bcsj.62.2913

  日期：1989.9

  Hexacarbonylmolybdenum(0)-induced dechalcogenization of allylic sulfides I, sulfones II, and selenides III in refluxing dioxane, which led to nucleophilic substitutions with carbon nucleophiles. Attack of the relatively bulky nucleophile, 2-ethoxycarbonyl-2-sodiocyclopentanone occurred regioselectively at the less substituted end of the allyl unit after the dechalcogenization to give only one isomer

  六羰基钼 (0) 诱导的烯丙基硫化物 I、砜 II 和硒化物 III 在回流的二恶烷中脱硫，导致碳亲核试剂发生亲核取代。相对庞大的亲核试剂 2-乙氧羰基-2-钠基环戊酮的攻击在脱硫后烯丙基单元的较少取代末端发生区域选择性，仅产生一种异构体。钠丙二酸二乙酯对 I 和 III 的攻击优先发生在 γ 位，而对 II 的攻击优先发生在脱磺酰化后烯丙基单元的更多取代端。在没有碳亲核试剂的情况下，在回流的二恶烷中用 Mo(CO)6 处理​​ I、II 和 III 导致还原性脱硫。H2O 的加入加速了还原脱硫。
• Microwave-enhanced Pd(0)/acetic acid catalyzed allylation reactions of C, N, and O-pronucleophiles with alkynes
  作者：Nitin T. Patil、F. Nawaz Khan、Yoshinori Yamamoto

  DOI：10.1016/j.tetlet.2004.09.099

  日期：2004.11

  An efficient method for the allylation of C, N, and O-nucleophiles with alkynes under solvent-free conditions and by microwave activation is established. The process can be termed as a real eco-chemical process since no waste elements are produced in the reaction, moreover it is solvent free. This technique can also be used for the allylation of dimethyl methylmalonate, which proves inert under the

  建立了一种在无溶剂条件下并通过微波活化将C，N和O亲核试剂与炔烃进行烯丙基化的有效方法。该过程可以称为真正的生态化学过程，因为在反应中不产生任何废物，而且不含溶剂。该技术也可以用于丙二酸二甲酯的烯丙基化，这在先前报道的反应条件下证明是惰性的（在1,4-二恶烷中回流）。
• Synthesis of <i>gem</i>-Difluoromethylenated Bicyclo[<i>m.n.</i>0]alkan-1-ols and Their Ring-Expansion to <i>gem</i>-Difluoromethylenated Macrocyclic Lactones
  作者：Teerachai Punirun、Krisana Peewasan、Chutima Kuhakarn、Darunee Soorukram、Patoomratana Tuchinda、Vichai Reutrakul、Palangpon Kongsaeree、Samran Prabpai、Manat Pohmakotr

  DOI：10.1021/ol3004194

  日期：2012.4.6

  adduct afforded the corresponding gem-difluoromethylenated bicyclic compounds 4, which underwent ring-expansion followed by the Baeyer–Villiger-type oxidation of the resulting macrocyclic ketone intermediates to give gem-difluoromethylenated macrocyclic lactones 5.

  氟化物催化立体选择性亲核加成PhSCF的2森达3（1）〜α-carboethoxycycloalkanones 2，然后将所得的分子内自由基环化顺式- 3的加合物，得到相应的宝石-difluoromethylenated双环化合物4，后行环扩大随后贝耶尔其-所得大环酮中间体的维利格型氧化，得到宝石-二氟甲基化的大环内酯5。
• Palladium-Catalyzed, Carboxylic Acid-Assisted Allylic Substitution of Carbon Nucleophiles with Allyl Alcohols as Allylating Agents in Water
  作者：Kei Manabe、Shū Kobayashi

  DOI：10.1021/ol035126q

  日期：2003.9.1

  [structure: see text] Allylic substitution of allyl alcohols in water as a suspension medium has been realized using a combination of tetrakis(triphenylphosphine)palladium and a carboxylic acid such as 1-adamantanecarboxylic acid. Various substrates turned out to be applicable to this catalytic system.

  [结构：见正文]使用四（三苯基膦）钯和羧酸如1-金刚烷羧酸的组合已经实现了作为悬浮介质的水中烯丙醇的烯丙基取代。事实证明，各种底物可适用于该催化体系。