1-phenylethynyl-bicyclo[4.1.0]heptan-2-one | 917087-34-4

• 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: 1-phenylethynyl-bicyclo[4.1.0]heptan-2-one
• 英文别名: 1-(2-Phenylethynyl)bicyclo[4.1.0]heptan-2-one
• CAS: 917087-34-4
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: VEUZMLNELLQXLC-UHFFFAOYSA-N

物化性质

• 熔点：
  52-53 °C
• 沸点：
  352.7±25.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-phenylethynyl-bicyclo[4.1.0]heptan-2-one 在 碘 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到5,6,7,8-tetrahydro-3,5-diiodo-2-phenyl-4H-cyclohepta[b]furan
  参考文献：
  名称：

  通过1-（1-炔基）-环丙基酮的亲电环化有效合成高度取代的呋喃

  摘要：

  1-（1-炔基）-环丙基酮的亲电子环化反应在极其温和的反应条件下提供了一种高效，直接的途径来取代高度取代的呋喃。碘，NIS和PhSeBr已证明在此过程中作为亲电子试剂是成功的。

  DOI：

  10.1016/j.tetlet.2008.02.081
• 作为产物：
  描述：

  三甲基碘化亚砜 、 2-(苯基乙炔基)环己-2-烯-1-酮 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 以70%的产率得到1-phenylethynyl-bicyclo[4.1.0]heptan-2-one
  参考文献：
  名称：

  Stereospecificity of the Au(I)-catalyzed reaction of 1-alkynyl-bicyclo[4.1.0]-heptan-2-ones with nucleophiles

  摘要：

  The stereospecificity of the Au(I)-catalyzed reaction of 1-alkynyl-bicyclo[4.1.0]-heptan-2-ones with nucleophiles was investigated. The substrates were prepared in non-racemic form (up to 88% ee) through parallel kinetic resolution (CBS reduction) and reoxidation of the separated diastereomeric alcohols. The key Au-catalyzed reaction was then found to proceed without significant loss of absolute stereochemical information: this way, an achiral carbocationic intermediate could be excluded. Thus, a bicyclobutonium-type intermediate seems to be attacked in a S(N)2-type fashion by the nucleophile in accordance with computational predictions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.05.019

文献信息

• Gold-Catalyzed Cascade Cyclization and 1,3-Difunctionalization To Access Polysubstituted Furans
  作者：Yong Xu、Jiangtao Sun

  DOI：10.1021/acs.orglett.0c04090

  日期：2021.2.5

  Gold-catalyzed cascade cyclization and 1,3-difunctionalization of 2-(1-alkyny)-2-alken-1-ones with N,O-acetals are described, leading to the discovery of novel 1,3-oxyaminomethylation and 1,3-aminomethylamination. Typically, by varying the reaction conditions especially the gold catalysts, these two distinct reaction pathways can be controlled in a selective manner. Moreover, tandem cyclization and

  描述了金催化的N，O-乙缩醛对2-（1-炔基）-2-烯烃-1-酮的级联环化和1,3-双官能团的反应，从而发现了新颖的1,3-氧氨基甲基化和1， 3-氨基甲基氨基化。通常，通过改变反应条件，特别是金催化剂，可以以选择性的方式控制这两个不同的反应路径。此外，还实现了串联环化和1，4-氧氨基甲基化。
• Highly Efficient Synthesis of Multisubstituted Furans through Cupric Halide-Mediated Intramolecular Halocyclization of 1-(1-Alkynyl)cyclopropyl Ketones
  作者：Mei Zhu、Wei-Jun Fu、Chen Xu、Guang-Long Zou、Zhi-Qiang Wang、Bao-Ming Ji

  DOI：10.1002/ejoc.201200601

  日期：2012.8

  A convenient and efficient method for the synthesis of 3-halofurans was developed by using a cascade reaction between 1-(1-alkynyl)cyclopropyl ketones and cupric halide. Under mild reaction conditions, both 3-chloro- and 3-bromofuran derivatives were obtained in high yields. The reaction involves consecutive multiple bond formations, includingC–O and C–Br bonds, with high regioselectivity. Mechanistic

  通过使用 1-(1-炔基) 环丙基酮和卤化铜之间的级联反应，开发了一种方便有效的合成 3-卤代呋喃的方法。在温和的反应条件下，3-氯-和3-溴呋喃衍生物均以高产率获得。该反应涉及连续的多重键形成，包括 C-O 和 C-Br 键，具有高区域选择性。描述了机械方面。
• Synthesis of Polysubstituted Pyrroles through the Tandem 1,3-Addition/5-<i>endo</i>-<i>dig</i>Cyclization of 1-(1-Alkynyl)cyclopropyl Imines
  作者：Aurelija Urbanaitė、Inga Čikotienė

  DOI：10.1002/ejoc.201600985

  日期：2016.11

  Cyclopropyl-tethered 3-alkynyl imines react with polarized-covalent-bond-containing compounds to give polyfunctionalized pyrroles. This provides a mild and effective method for the simultaneous introduction of halogen, chalcogen, or hydrogen groups to the 3-position of the pyrrole ring, together with the incorporation of halogen, azide, or alkoxy/aryloxy groups into the ethyl side-chain.

  环丙基连接的 3-炔基亚胺与极化的含共价键的化合物反应，得到多官能化的吡咯。这为同时将卤素、硫属元素或氢基团引入到吡咯环的 3-位，以及将卤素、叠氮化物或烷氧基/芳氧基引入乙基侧链提供了一种温和而有效的方法。
• Gold(I)-Catalyzed Reaction of 1-(1-Alkynyl)-cyclopropyl Ketones with Nucleophiles: A Modular Entry to Highly Substituted Furans
  作者：Junliang Zhang、Hans-Günther Schmalz

  DOI：10.1002/anie.200601252

  日期：2006.10.13
• Highly Substituted Pyrroles by a Gold(I)-Catalyzed Tandem Reaction of 1-(1-Alkynyl)cyclopropyl Oxime Ethers with Nucleophiles
  作者：Junliang Zhang、Yanqing Zhang

  DOI：10.1055/s-0031-1290978

  日期：2012.6

  A gold(I)-catalyzed tandem reaction of 1-(1-alkynyl) cyclopropyl oxime ethers with nucleophiles under mild conditions has been developed, which provides a facile access to highly substituted pyrroles in moderate to excellent yields.