3-(3-氧代环己烯-1-基)丙酸 | 61563-62-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(3-氧代环己烯-1-基)丙酸
• 英文名称: 3-(3-oxocyclohex-1-enyl)propanoic acid
• 英文别名: 3-(3-Oxocyclohex-1-en-1-yl)propanoic acid；3-(3-oxocyclohexen-1-yl)propanoic acid
• CAS: 61563-62-0
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: NCTKBYROEJKJCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  348.7±31.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-氧代环己烯-1-基)丙酸 以 四氢呋喃 、 乙醚 为溶剂， 生成 3-(3-Hydroxy-3-methyl-butyl)-1-methyl-cyclohex-2-enol
  参考文献：
  名称：

  Amberlyst-15-catalyzed intramolecular SN2′ oxaspirocyclization of tertiary allylic alcohols

  摘要：

  A variety of substituted 1-oxaspiro[4,5]dec-6-ene and 1-oxaspiro[5,5]undec-7-ene systems have been prepared by utilizing Amberlyst-15-catalyzed S(N)2' oxaspirocyclizations under mild reaction conditions (-20 degrees C) in quantitative yields. In this process, a tertiary allylic alcohol serves as the precursor of pi-allylic carbocation and the primary, secondary or tertiary alcohol within the same molecule serves as the nucleophile, (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00390-7
• 作为产物：
  描述：

  3-(3-hydroxypropyl)-2-cyclohexenone 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 3-(3-氧代环己烯-1-基)丙酸
  参考文献：
  名称：

  Amberlyst-15催化仲烯丙基醇的分子内S N 2'氧螺环化。在螺环醚theaspirane和theaspirone的全合成中的应用

  摘要：

  各种取代的1-氧杂螺[4.4]非6-烯，1-氧杂螺[4.5] dec-6-烯，6-氧杂螺[4.5] dec-1-烯和1-氧杂螺[5.5] undec-7-通过在温和的反应条件下以定量收率利用仲烯丙基醇的Amberlyst-15催化的分子内S N 2'氧代螺环化反应制备烯键体系。该氧杂螺环化以五个步骤应用于从β-紫罗兰酮的茶皮螺烷和茶皮螺酮的全合成中。

  DOI：

  10.1016/s0040-4039(00)00396-8

文献信息

• Amberlyst-15-catalyzed intramolecular SN2′ oxaspirocyclization of secondary allylic alcohols. Application to the total synthesis of spirocyclic ethers theaspirane and theaspirone
  作者：Jenn-jong Young、Liarng-jyur Jung、Kuang-ming Cheng

  DOI：10.1016/s0040-4039(00)00396-8

  日期：2000.4

  1-oxaspiro[5.5]undec-7-ene systems have been prepared by utilizing Amberlyst-15-catalyzed intramolecular SN2′ oxaspirocyclizations of secondary allylic alcohols under mild reaction conditions in quantitative yields. This oxaspirocyclization was applied to the total synthesis of theaspirane and theaspirone from β-ionone in five steps.

  各种取代的1-氧杂螺[4.4]非6-烯，1-氧杂螺[4.5] dec-6-烯，6-氧杂螺[4.5] dec-1-烯和1-氧杂螺[5.5] undec-7-通过在温和的反应条件下以定量收率利用仲烯丙基醇的Amberlyst-15催化的分子内S N 2'氧代螺环化反应制备烯键体系。该氧杂螺环化以五个步骤应用于从β-紫罗兰酮的茶皮螺烷和茶皮螺酮的全合成中。
• A Facile Approach to the Synthesis of Allylic Spiro Ethers and Lactones
  作者：Ming-Chang Yeh、Yi-Chin Lee、Tsao-Ching Young

  DOI：10.1055/s-2006-950294

  日期：2006.11

  Treatment of 3-[(alkoxycarbonyl)alkyl]-substituted conjugated cycloalkenones with diisobutylaluminum hydride at -78 °C followed by acid quenching furnishes spiro ethers, whereas the corresponding 3-(carboxyalkyl)-substituted cycloalkenones generate spiro lactones upon reaction with sodium borohydride at 30 °C followed by acid quenching.

  3-[(alkoxycarbonyl)alkyl]-substituted conjugated cycloalkenones with diisobutylaluminum hydride at -78 °C and followed by acid quenching furnishes spiro ethers, 而相应的 3-(carboxyalkyl)-substituted cycloalkenones generated spiro lactones upon reaction with sodium borohydride at 30 °C and followed by acid quenching.
• Bryson,T.A.; Wilson,C.A., Synthetic Communications, 1976, vol. 6, p. 521 - 526
  作者：Bryson,T.A.、Wilson,C.A.

  DOI：——

  日期：——
• Amberlyst-15-catalyzed intramolecular SN2′ oxaspirocyclization of tertiary allylic alcohols
  作者：Jenn-jong Young、Liarng-jyur Jung、Kuang-ming Cheng

  DOI：10.1016/s0040-4039(00)00390-7

  日期：2000.4

  A variety of substituted 1-oxaspiro[4,5]dec-6-ene and 1-oxaspiro[5,5]undec-7-ene systems have been prepared by utilizing Amberlyst-15-catalyzed S(N)2' oxaspirocyclizations under mild reaction conditions (-20 degrees C) in quantitative yields. In this process, a tertiary allylic alcohol serves as the precursor of pi-allylic carbocation and the primary, secondary or tertiary alcohol within the same molecule serves as the nucleophile, (C) 2000 Elsevier Science Ltd. All rights reserved.