1-cyclopropyl-5-phenylpent-4-yn-1-one | 1342263-96-0

• 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-cyclopropyl-5-phenylpent-4-yn-1-one
• CAS: 1342263-96-0
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: ZSNTWYWFAYQXTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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-cyclopropyl-5-phenylpent-4-yn-1-one 在 正丁基锂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 5.83h， 生成 3-cyclopropyl-7-phenylhepta-1,6-diyn-3-yl benzoate
  参考文献：
  名称：

  Gold-Catalyzed Cycloisomerization of 1,6-Diyne Carbonates and Esters to 2,4a-Dihydro-1H-fluorenes

  摘要：

  A synthetic method to prepare 2,4a-dihydro-1H-fluorenes efficiently from gold(I)-catalyzed 1,2-acyloxy migration/cyclopropenation/Nazarov cyclization of 1,6-diyne carbonates and esters is described. The suggested reaction pathway provides rare examples of [2,3]-sigmatropic rearrangement in this class of compounds as well as the involvement of an in situ formed cyclopropene intermediate in gold catalysis. Experimental and ONIOM(QM:QM') [our own n-layered integrated molecular orbital and molecular mechanics(quantum mechanics quantum mechanics')] computational studies based on the proposed Au carbenoid species provide insight into this unique selectivity.

  DOI：

  10.1021/ja4032727
• 作为产物：
  描述：

  5-苯基戊-4-炔酸 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-cyclopropyl-5-phenylpent-4-yn-1-one
  参考文献：
  名称：

  Gold-Catalyzed Enantioselective Ring-Expanding Cycloisomerization of Cyclopropylidene Bearing 1,5-Enynes

  摘要：

  An enantioselective ring-expanding cycloisomerization of 1,5-enynes bearing a cyclopropylidene moiety has been developed. This methodology provides a new approach to bicyclo[4.2.0]octanes, a structural motif present in many biologically active natural products.

  DOI：

  10.1021/ol5007955

文献信息

• Gold-Catalyzed Cycloisomerization of 1,6-Diyne Carbonates and Esters to 2,4a-Dihydro-1<i>H</i>-fluorenes
  作者：Weidong Rao、Ming Joo Koh、Dan Li、Hajime Hirao、Philip Wai Hong Chan

  DOI：10.1021/ja4032727

  日期：2013.5.29

  A synthetic method to prepare 2,4a-dihydro-1H-fluorenes efficiently from gold(I)-catalyzed 1,2-acyloxy migration/cyclopropenation/Nazarov cyclization of 1,6-diyne carbonates and esters is described. The suggested reaction pathway provides rare examples of [2,3]-sigmatropic rearrangement in this class of compounds as well as the involvement of an in situ formed cyclopropene intermediate in gold catalysis. Experimental and ONIOM(QM:QM') [our own n-layered integrated molecular orbital and molecular mechanics(quantum mechanics quantum mechanics')] computational studies based on the proposed Au carbenoid species provide insight into this unique selectivity.
• Gold-Catalyzed Enantioselective Ring-Expanding Cycloisomerization of Cyclopropylidene Bearing 1,5-Enynes
  作者：Hongchao Zheng、Ryan J. Felix、Michel R. Gagné

  DOI：10.1021/ol5007955

  日期：2014.4.18

  An enantioselective ring-expanding cycloisomerization of 1,5-enynes bearing a cyclopropylidene moiety has been developed. This methodology provides a new approach to bicyclo[4.2.0]octanes, a structural motif present in many biologically active natural products.