3-ethylcarbonyl-4-(1-ethyl-2-ethoxycarbonylpropenic acid ethyl ester)-2,5-dihydrofuran

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-ethylcarbonyl-4-(1-ethyl-2-ethoxycarbonylpropenic acid ethyl ester)-2,5-dihydrofuran
• 英文别名: 2-[1-(4-propionyl-2,5-dihydrofuran-3-yl)propylidene]malonic acid diethyl ester；Diethyl 2-[1-(4-propanoyl-2,5-dihydrofuran-3-yl)propylidene]propanedioate；diethyl 2-[1-(4-propanoyl-2,5-dihydrofuran-3-yl)propylidene]propanedioate
• 化学式: C₁₇H₂₄O₆
• 分子量: 324.374
• InChiKey: ZVWAFBGCIOXSKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  di(2-pentynyl) ether 、 酮基丙二酸二乙酯 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以84%的产率得到3-ethylcarbonyl-4-(1-ethyl-2-ethoxycarbonylpropenic acid ethyl ester)-2,5-dihydrofuran
  参考文献：
  名称：

  羰基化合物与1,6-二炔的阳离子Rh（I）/改性BINAP催化反应，生成二烯酮和邻位官能化的芳基酮。

  摘要：

  我们已经确定，阳离子铑（I）/ H8-BINAP络合物催化活化和未活化的羰基化合物与1，6-二炔的[2 + 2 + 2]环加成反应，从而高产率地生成二烯酮。另一方面，未活化的芳基酮在阳离子铑（I）/ Segphos络合物的存在下与1,6-二炔反应，从而以高收率得到邻位官能化的芳基酮。

  DOI：

  10.1021/ol0707721

文献信息

• Cationic Rh(I)/Modified-BINAP-Catalyzed Reactions of Carbonyl Compounds with 1,6-Diynes Leading to Dienones and Ortho-Functionalized Aryl Ketones
  作者：Ken Tanaka、Yousuke Otake、Azusa Wada、Keiichi Noguchi、Masao Hirano

  DOI：10.1021/ol0707721

  日期：2007.5.1

  rhodium(I)/H8-BINAP complex catalyzes a [2 + 2 + 2] cycloaddition of both activated and unactivated carbonyl compounds with 1,6-diynes leading to dienones in high yields. On the other hand, unactivated aryl ketones react with 1,6-diynes in the presence of a cationic rhodium(I)/Segphos complex to give ortho-functionalized aryl ketones in high yields.

  我们已经确定，阳离子铑（I）/ H8-BINAP络合物催化活化和未活化的羰基化合物与1，6-二炔的[2 + 2 + 2]环加成反应，从而高产率地生成二烯酮。另一方面，未活化的芳基酮在阳离子铑（I）/ Segphos络合物的存在下与1,6-二炔反应，从而以高收率得到邻位官能化的芳基酮。
• Reactions of Zirconacyclopentadienes with CO, CN, and NN Moieties with Electron-Withdrawing Groups:  Formation of Six-Membered Heterocycles
  作者：Tamotsu Takahashi、Yanzhong Li、Taichi Ito、Feng Xu、Kiyohiko Nakajima、Yuanhong Liu

  DOI：10.1021/ja010678u

  日期：2002.2.1

  Reactions of zirconacyclopentadienes with diethyl ketomalonate gave alpha-pyrans in excellent yields in the presence of BiCl3. In the absence of BiCl3, zirconacyclopentadienes did not react with diethyl ketomalonate. Tetraphenylzirconacyclopentadiene reacted with diethyl ketomalonate in the presence of BiCl3 to give a ring-opening product, dienolic ether, in 53% yield. The structures of the alpha-pyran prepared from diethyldiphenylzirconacyclopentadiene and the ring-opening product were determined by X-ray analysis. When oximinosulfonate was added to tetraethylzirconacyclopentadiene in THF at -78 degrees C, 3,4,5,6-tetraethylpyridine-2-carbonitrile was obtained in 95% yield within 10 min. The structure of the product was confirmed by X-ray analysis. When tetraethylzirconacyclopentadiene was treated with azodicarboxylate in the presence of 2 equiv of CuCl at -78 degrees C, 1,2-dialkoxycarbonyl-3,4,5,6-tetraethyl-1,2-dihydropyridazine derivatives were obtained. The structure of one of dihydropyridazine was also confirmed by X-ray analysis.
• Cationic Rhodium(I)/H₈-binap Complex Catalyzed [2+2+2] Cycloadditions of 1,6- and 1,7-Diynes with Carbonyl Compounds
  作者：Yousuke Otake、Rie Tanaka、Ken Tanaka

  DOI：10.1002/ejoc.200900185

  日期：2009.6

  catalyzes [2+2+2] cycloadditions of a variety of 1,6- and 1,7-diynes with both electron-deficient and electron-rich carbonyl compounds, leading to dienones in high yield under mild reaction conditions. In the reactions with acyl phosphonates, the reactivity of 1,6- and 1,7-diynes was highly dependent on their own structures. The addition of chelating diethyl oxalate effectively promoted the [2+2+2] cycloadditions

  我们已经确定阳离子铑 (I)/H8-binap 络合物可催化各种 1,6- 和 1,7-二炔与缺电子和富电子羰基化合物的 [2+2+2] 环加成，导致在温和的反应条件下高产率的二烯酮。在与酰基膦酸酯的反应中，1,6- 和 1,7- 二炔的反应性高度依赖于它们自身的结构。螯合草酸二乙酯的添加有效地促进了涉及酰基膦酸酯的 [2+2+2] 环加成，这可能是由于二炔和酰基膦酸酯之间通过简单的配体交换平衡形成了所需的二炔和酰基膦酸酯的 1:1 铑配合物。弱配位的草酸二乙酯。在涉及双功能羰基化合物或不对称 1,6-二炔的反应中，观察到高化学或区域选择性。