Prop-2-enyl 2-acetylhept-6-ynoate | 855420-86-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: Prop-2-enyl 2-acetylhept-6-ynoate
• CAS: 855420-86-9
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: UUTOSGOEEFNCCF-UHFFFAOYSA-N

物化性质

• 沸点：
  305.0±37.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  Prop-2-enyl 2-acetylhept-6-ynoate 在 potassium tetrachloroaurate(III) air 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以94%的产率得到2-propenyl 1-(1-oxoethyl)-2-methylenecyclopentanecarboxylate
  参考文献：
  名称：

  大体积硫脲作为金 (I) 催化 1,3-二羰基化合物环化的新配体

  摘要：

  我们说明了第一次使用庞大的 N,N'-二取代环状硫脲作为金 (I) 催化的配体。硫脲-金 (I) 配合物的 X 射线晶体结构提供了有关配合物性质的重要信息。发现这些配合物是 1,3-二羰基化合物与炔烃的环化反应（Conia-ene 反应）的活性催化剂。在 1 mol% 的硫脲-氯化金 (I) 络合物和三氟甲磺酸银存在下，各种炔属 1,3-二羰基化合物经过环化异构化得到单环和双环烯属环戊烷。

  DOI：

  10.1055/s-2007-983804
• 作为产物：
  描述：

  乙酰乙酸烯丙酯 、 戊-4-炔基对甲苯磺酸酯 在 sodium hydride 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 Prop-2-enyl 2-acetylhept-6-ynoate
  参考文献：
  名称：

  1,3-二羰基化合物与炔烃的常规锌催化Conia-Ene反应，包括在纯净条件下具有经典挑战性的底物

  摘要：

  通过锌催化1,3-二羰基化合物与炔烃的分子内Conia-ene反应，已经开发出一种简单的，多用途的新方法，可将四元环变成六元环。这种新途径允许将广泛的二羰基化合物，包括经典的具有挑战性的1,3-二酯和N，N'-二取代的1,3-酮酰胺，用于与廉价氯化锌（ZnCl 2）。

  DOI：

  10.1002/adsc.200900588

文献信息

• Development of an enantioselective amine–silver co-catalyzed Conia-ene reaction
  作者：M. Blümel、D. Hack、L. Ronkartz、C. Vermeeren、D. Enders

  DOI：10.1039/c7cc01807j

  日期：——

  The development of a novel cooperative catalytic system for an amine–silver co-catalyzed Conia-ene reaction of alkyne-tethered C–H-acidic compounds is reported.

  报道了一种新型的合作催化系统，用于氨基-银共催化的炔基-锚定C-H酸性化合物的Conia-ene反应。
• Bulky Thioureas as New Ligands for Gold(I)-Catalyzed Cyclization of Acetylenic 1,3-Dicarbonyl Compounds
  作者：Dan Yang、Jie-Hui Pan、Min Yang、Qiang Gao、Nian-Yong Zhu

  DOI：10.1055/s-2007-983804

  日期：2007.8

  N′-disubstituted cyclic thioureas as ligands for gold(I) catalysis. X-ray crystal structures of the thiourea-gold(I) complexes presented important information about the nature of the complexation. These complexes were found to be active catalysts for the cyclization of 1,3-dicarbonyl compounds with alkynes (Conia-ene reaction). Various acetylenic 1,3-dicarbonyl compounds underwent cycloisomerization to give mono-

  我们说明了第一次使用庞大的 N,N'-二取代环状硫脲作为金 (I) 催化的配体。硫脲-金 (I) 配合物的 X 射线晶体结构提供了有关配合物性质的重要信息。发现这些配合物是 1,3-二羰基化合物与炔烃的环化反应（Conia-ene 反应）的活性催化剂。在 1 mol% 的硫脲-氯化金 (I) 络合物和三氟甲磺酸银存在下，各种炔属 1,3-二羰基化合物经过环化异构化得到单环和双环烯属环戊烷。
• Efficient Formation of Ring Structures Utilizing Multisite Activation by Indium Catalysis
  作者：Yoshimitsu Itoh、Hayato Tsuji、Ken-ichi Yamagata、Kohei Endo、Iku Tanaka、Masaharu Nakamura、Eiichi Nakamura

  DOI：10.1021/ja805657h

  日期：2008.12.17

  Lewis acidic indium(III) salts, in particular In(NTf2)(3), effect the conversion of alpha-(omega'-alkynyl)-beta-ketoesters; and omega-alkynyl-beta-ketoesters to the corresponding cyclic products in a manner known as the Coniaene reaction. This reaction can lead to the creation of five- to fifteen-membered-ring carbocycles and heterocycles in good to excellent yields. The synthetic features of the reaction are a relatively low catalyst loading, as low as 0.01 mol % in the best case, as well as no requirement of solvent for five-membered-ring formation and the requirement of only moderately dilute reaction conditions for medium-sized-ring formation. The high reactivity of indium salts is due to the double activation of the beta-ketoester substrate containing an acetylene function. The indium metal activates the beta-ketoester moiety by the formation of an indium enolate, and this indium metal electrophilically activates the alkyne moiety. Such a strong push-pull activation of the substrate by a single metal circumvents the disadvantage of entropic and enthalpic factors generally associated with the formation of medium- and large-sized rings. The reaction allows the ready formation of a fifteen-membered-ring carbocycle, from which di-muscone has been synthesized.
• Ni(II)-Catalyzed Conia-Ene Reaction of 1,3-Dicarbonyl Compounds with Alkynes
  作者：Qiang Gao、Bao-Fu Zheng、Jin-Heng Li、Dan Yang

  DOI：10.1021/ol050532q

  日期：2005.5.1

  We have discovered a Ni(II)-catalyzed Conia-ene reaction of 1,3-dicarbonyl compounds with alkynes. In the presence of Ni(acac)(2) and Yb(OTf)(3), various acetylenic 1,3-dicarbonyl compounds underwent Conia-ene reaction to give mono- and bicyclic olefinic cyclopentanes. A mechanism involving the enol-yne-Ni complex formation is proposed and supported by deuterium-labeling experiments.
• General Zinc-Catalyzed Conia-Ene Reactions of 1,3-Dicarbonyl Compounds with Alkynes Including the Classically Challenging Substrates under Neat Conditions
  作者：Chen-Liang Deng、Ren-Jie Song、Yi-Lin Liu、Jin-Heng Li

  DOI：10.1002/adsc.200900588

  日期：2009.12

  products has been developed by zinc-catalyzed intramolecular Conia-ene reactions of 1,3-dicarbonyl compounds with alkynes. This new route allows a wide range of dicarbonyl compounds, including the classically challenging 1,3-diesters and N,N′-disubstituted 1,3-keto amides, to be used for the Conia-ene reaction with inexpensive zinc chloride (ZnCl2) under neat conditions.

  通过锌催化1,3-二羰基化合物与炔烃的分子内Conia-ene反应，已经开发出一种简单的，多用途的新方法，可将四元环变成六元环。这种新途径允许将广泛的二羰基化合物，包括经典的具有挑战性的1,3-二酯和N，N'-二取代的1,3-酮酰胺，用于与廉价氯化锌（ZnCl 2）。