trans-3'-phenylallyl 1-hydroxycyclohexanecarboxylate

• 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: trans-3'-phenylallyl 1-hydroxycyclohexanecarboxylate
• 英文别名: [(E)-3-phenylprop-2-enyl] 1-hydroxycyclohexane-1-carboxylate
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: HREGGWOWBZYQTA-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (三苯基膦烯)乙烯酮 、 trans-3'-phenylallyl 1-hydroxycyclohexanecarboxylate 在 苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以82%的产率得到4-(trans-3'-phenylallyloxy)-1-oxaspiro[4.5]dec-3-en-2-one
  参考文献：
  名称：

  An Unusual Domino Claisen−Conia Reaction Producing 3,5-Dispirodihydrofuran-2,4-diones

  摘要：

  Allyl tetronates 3 can be selectively converted either (in acetonitrile) into Claisen-rearranged 3-allyltetronic adds 5 or (in toluene) into novel Claisen-Conia-rearranged 3-(spirocyclopropyl)dihydrofuran-2,4-diones 6, featuring up to three new stereogenic centres. The mechanism and the stereochemistry of this process is discussed and an X-ray crystal structure of one of the two diastereoisomers of (+/-)-6c is presented.

  DOI：

  10.1002/1099-0690(200105)2001:10<1951::aid-ejoc1951>3.0.co;2-y
• 作为产物：
  描述：

  Alpha-羟基-环己基甲酸 、 N,N'-dicyclohexyl-O-(trans-3'-phenylallyl)isourea 以 四氢呋喃 为溶剂， 反应 16.0h， 以72%的产率得到trans-3'-phenylallyl 1-hydroxycyclohexanecarboxylate
  参考文献：
  名称：

  An Unusual Domino Claisen−Conia Reaction Producing 3,5-Dispirodihydrofuran-2,4-diones

  摘要：

  Allyl tetronates 3 can be selectively converted either (in acetonitrile) into Claisen-rearranged 3-allyltetronic adds 5 or (in toluene) into novel Claisen-Conia-rearranged 3-(spirocyclopropyl)dihydrofuran-2,4-diones 6, featuring up to three new stereogenic centres. The mechanism and the stereochemistry of this process is discussed and an X-ray crystal structure of one of the two diastereoisomers of (+/-)-6c is presented.

  DOI：

  10.1002/1099-0690(200105)2001:10<1951::aid-ejoc1951>3.0.co;2-y

文献信息

• An Unusual Domino Claisen−Conia Reaction Producing 3,5-Dispirodihydrofuran-2,4-diones
  作者：Rainer Schobert、Sven Siegfried、Gary Gordon、Mark Nieuwenhuyzen、Stig Allenmark

  DOI：10.1002/1099-0690(200105)2001:10<1951::aid-ejoc1951>3.0.co;2-y

  日期：2001.5

  Allyl tetronates 3 can be selectively converted either (in acetonitrile) into Claisen-rearranged 3-allyltetronic adds 5 or (in toluene) into novel Claisen-Conia-rearranged 3-(spirocyclopropyl)dihydrofuran-2,4-diones 6, featuring up to three new stereogenic centres. The mechanism and the stereochemistry of this process is discussed and an X-ray crystal structure of one of the two diastereoisomers of (+/-)-6c is presented.