2-(4-氯苯基)-3-甲基环戊-2-烯-1-酮 | 87506-06-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-氯苯基)-3-甲基环戊-2-烯-1-酮
• 英文名称: 2-(4-chlorophenyl)-3-methyl-2-cyclopenten-1-one
• 英文别名: 2-(4-Chlorophenyl)-3-methylcyclopent-2-en-1-one
• CAS: 87506-06-7
• 化学式: C₁₂H₁₁ClO
• 分子量: 206.672
• InChiKey: OIHCCUFBBJSVFK-UHFFFAOYSA-N

物化性质

• 沸点：
  338.3±42.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-<(4-chlorophenyl)methoxymethyl>-2-methylene-1-(trimethylsiloxy)cyclobutane 在 三氟乙酸 作用下， 生成 2-(4-氯苯基)-3-甲基环戊-2-烯-1-酮
  参考文献：
  名称：

  琥珀酸衍生物的环扩展。合成环戊烯的新途径

  摘要：

  带有邻位取代的二醇基团的环丁烷衍生物的酸催化的扩环反应以良好的产率得到α-芳基和α-乙烯基取代的环戊烯酮。

  DOI：

  10.1039/c39830000498

文献信息

• Catalytic Intermolecular Pauson−Khand-Type Reaction:  Strong Directing Effect of Pyridylsilyl and Pyrimidylsilyl Groups and Isolation of Ru Complexes Relevant to Catalytic Reaction
  作者：Kenichiro Itami、Koichi Mitsudo、Kazuyoshi Fujita、Youichi Ohashi、Jun-ichi Yoshida

  DOI：10.1021/ja047484+

  日期：2004.9.1

  Some circumstantial evidence for the directing effect of the 2-pyridylsilyl group in the Ru-catalyzed intermolecular Pauson-Khand-type reaction (PKR) of alkenyl(2-pyridyl)silane, alkyne, and carbon monoxide has been provided. Most importantly, we have succeeded in isolating several monometallic Ru complexes relevant to the catalytic reaction: Ru(vinylsilane)(CO)(3) complexes and ruthenacyclopentene. While the stoichimetric reaction of the Ru(vinylsilane)(CO)(3) complex with an alkyne led to the formation of the corresponding cyclopentenone (PKR product) at 100 degreesC, the ruthenacyclopentene intermediate was quantitatively produced at 50 degreesC. This complex was also converted to a cyclopentenone upon heating at 100 degreesC. Moreover, it was also found that the Ru(vinylsilane)(CO)(3) complex and ruthenacyclopentene serve as catalysts in intermolecular PKR.
• NAKAMURA, EIICHI;SHIMADA, JUN-ICHI;KUWAJIMA, ISAO, J. CHEM. SOC. CHEM. COMMUN., 1983, N 9, 498-499
  作者：NAKAMURA, EIICHI、SHIMADA, JUN-ICHI、KUWAJIMA, ISAO

  DOI：——

  日期：——
• SHIMADA, J. -ICHI;HASHIMOTO, KOICHI;KIM, BYEANG, HYEAN;NAKAMURA, EIICHI;K+, J. AMER. CHEM. SOC., 1984, 106, N 6, 1759-1773
  作者：SHIMADA, J. -ICHI、HASHIMOTO, KOICHI、KIM, BYEANG, HYEAN、NAKAMURA, EIICHI、K+

  DOI：——

  日期：——
• Ring expansion of succinoin derivatives. New synthetic routes to cyclopentenones
  作者：Eiichi Nakamura、Jun-ichi Shimada、Isao Kuwajima

  DOI：10.1039/c39830000498

  日期：——

  Acid-catalysed ring expansion reactions of cyclobutane derivatives bearing a vicinal substituted-diol group give α-aryl and α-vinyl substituted cyclopentenones in good yields.

  带有邻位取代的二醇基团的环丁烷衍生物的酸催化的扩环反应以良好的产率得到α-芳基和α-乙烯基取代的环戊烯酮。