4-phenyl-penta-2,3-dienoic acid ethyl ester | 65359-73-1

• 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: 4-phenyl-penta-2,3-dienoic acid ethyl ester
• 英文别名: ethyl 4-phenylpenta-2,3-dienoate；racem.-4-Phenyl-2.3-pentadiensaeure-ethylester；Ethyl-4-phenyl-penta-2,3-dienat
• CAS: 65359-73-1
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: QZBRGFQURDREQR-UHFFFAOYSA-N

物化性质

• 沸点：
  326.3±12.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  4-phenyl-penta-2,3-dienoic acid ethyl ester 生成 4-苯基戊-2,3-二烯酸
  参考文献：
  名称：

  Runge,W. et al., Justus Liebigs Annalen der Chemie, 1975, p. 1361 - 1378

  摘要：

  DOI：
• 作为产物：
  描述：

  重氮乙酸乙酯 、 methyl phenyl ketene 在 5,10,15,20-tetrakis(p-chlorophenyl)porphyrin iron(III) chloride 三苯基膦 作用下， 以 甲苯 为溶剂， 以99%的产率得到4-phenyl-penta-2,3-dienoic acid ethyl ester
  参考文献：
  名称：

  Iron Porphyrin-Catalyzed Olefination of Ketenes with Diazoacetate for the Enantioselective Synthesis of Allenes

  摘要：

  In the presence of Ph3P and catalytic Fe(TCP) Cl, ketenes could react with EDA to give allenes in high yields under neutral conditions for the first time. By employing chiral phosphine instead of PPh3, allenes could be synthesized with high enantioselectivity (93-98% ee) in good yields.

  DOI：

  10.1021/ja068642v

文献信息

• Bifunctionalized Allenes. Part VIII. An Efficient and Varied Method for the Synthesis of 2-Sulfonylated Alka-2,3-Dienoates
  作者：Ivaylo K. Ivanov、Valerij Ch. Christov

  DOI：10.1080/10426507.2012.718299

  日期：2013.7.1

  Abstract An efficient and varied method for the synthesis of 2-sulfonylated alka-2,3-dienoates by intermediate formation of allenecarboxylates, allenyl sulfones, and propargyl sulfinates using the relatively high acidity of the hydrogen atom at the allenic C-1 atom and the [2,3]-sigmatropic rearrangement is described. Supplemental materials are available for this article. Go to the publisher's online

  摘要 通过使用丙二烯 C-1 原子上相对高的氢原子酸度和丙二烯基亚磺酸酯中间体形成丙二烯羧酸酯、丙二烯基砜和炔丙基亚磺酸酯，合成 2-磺酰化的 2,3-二烯酸烷基酯的一种有效且多样的方法。描述了 [2,3]-σ 重排。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要
• Regio- and Stereoselective Alkenylation of Allenoates with <i>gem</i>-Difluoroalkenes: Facile Access to Fluorinated 1,4-Enynes Bearing an All-Carbon Quaternary Center
  作者：Qi-Qi Zhang、Shi-Yong Chen、E Lin、Honggen Wang、Qingjiang Li

  DOI：10.1021/acs.orglett.9b00775

  日期：2019.5.3

  A regio- and stereoselective synthesis of fluorinated 1,4-enynes bearing an all-carbon quaternary center at the propargylic position is developed. The synthesis starts from readily available allenoates and gem-difluoroalkenes and proceeds via a key alkynylenolate intermediate following a nucleophilic addition/β-F elimination. This reaction occurs under mild reaction conditions with good tolerance to

  开发了在炔丙基位置带有全碳四元中心的氟化1,4-烯炔的区域和立体选择性合成。从容易获得的联烯酸酯和合成启动宝石-difluoroalkenes并且进行经由键alkynylenolate中间以下的亲核加成/β-F的消除。该反应在对各种官能团具有良好耐受性的温和反应条件下发生。产品的进一步转化证明了合成的效用。此外，该反应还可以通过使用3，3-二取代的脲基酸酯而应用于α-烯基脲基酸酯的合成。
• Synthesis of Allenyl Esters by Horner–Wadsworth–Emmons Reactions of Ketenes Mediated by Isopropylmagnesium Bromide
  作者：Shigeki Sano、Tomoya Matsumoto、Teppei Yano、Munehisa Toguchi、Michiyasu Nakao

  DOI：10.1055/s-0034-1378803

  日期：——

  The synthesis of conjugated allenyl esters (tri-substituted allenes) was achieved by magnesium(II)-mediated Horner-Wadsworth-Emmons reaction of methyl bis(2,2,2-trifluoroethyl)phosphonoacetate with disubstituted ketenes. In addition, a novel access to -fluorinated allenyl carboxamides (tetrasubstituted allenes) is presented.
• Iron Porphyrin-Catalyzed Olefination of Ketenes with Diazoacetate for the Enantioselective Synthesis of Allenes
  作者：Chuan-Ying Li、Xiao-Bing Wang、Xiu-Li Sun、Yong Tang、Jun-Cheng Zheng、Zheng-Hu Xu、Yong-Gui Zhou、Li-Xin Dai

  DOI：10.1021/ja068642v

  日期：2007.2.1

  In the presence of Ph3P and catalytic Fe(TCP) Cl, ketenes could react with EDA to give allenes in high yields under neutral conditions for the first time. By employing chiral phosphine instead of PPh3, allenes could be synthesized with high enantioselectivity (93-98% ee) in good yields.
• Runge,W. et al., Justus Liebigs Annalen der Chemie, 1975, p. 1361 - 1378
  作者：Runge,W. et al.

  DOI：——

  日期：——