1-(1-hexynyl)-bicyclo[4.1.0]heptan-2-one | 917087-37-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1-hexynyl)-bicyclo[4.1.0]heptan-2-one
• 英文别名: 1-hex-1-ynyl-bicyclo[4.1.0]heptan-2-one；1-Hex-1-ynylbicyclo[4.1.0]heptan-2-one；1-hex-1-ynylbicyclo[4.1.0]heptan-2-one
• CAS: 917087-37-7
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: YRFJNYZGTUATJW-UHFFFAOYSA-N

物化性质

• 沸点：
  289.7±19.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 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-(1-hexynyl)-bicyclo[4.1.0]heptan-2-one 、 苯基溴化硒 以 二氯甲烷 为溶剂， 反应 1.0h， 以75%的产率得到5-bromo-2-butyl-3-phenylselanyl-5,6,7,8-tetrahydro-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-(1-hexynyl)-2-cyclohex-1-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 以43%的产率得到1-(1-hexynyl)-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(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
• Stereospecificity of the Au(I)-catalyzed reaction of 1-alkynyl-bicyclo[4.1.0]-heptan-2-ones with nucleophiles
  作者：Stephan Labsch、Shute Ye、Andreas Adler、Jörg-Martin Neudörfl、Hans-Günther Schmalz

  DOI：10.1016/j.tetasy.2010.05.019

  日期：2010.7

  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.
• An efficient synthesis of highly substituted furans via the electrophilic cyclization of 1-(1-alkynyl)-cyclopropyl ketones
  作者：Xian Huang、Weijun Fu、Maozhong Miao

  DOI：10.1016/j.tetlet.2008.02.081

  日期：2008.4

  The electrophilic cyclization of 1-(1-alkynyl)-cyclopropyl ketones offers an efficient and straightforward route to highly substituted furans under extremely mild reaction conditions. Iodine, NIS, and PhSeBr have proven successful as electrophiles in this process.

  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。