2,3-di(n-butyl)-2-cyclopentenone | 67238-19-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-di(n-butyl)-2-cyclopentenone
• 英文别名: 2,3-dibutylcyclopent-2-en-1-one；2,3-dibutyl-cyclopent-2-enone；2,3-dibutylcyclopenten-1-one；Dibutylcyclopentenone
• CAS: 67238-19-1
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: KPSVAVPXAWMJHR-UHFFFAOYSA-N

物化性质

• 沸点：
  287.8±10.0 °C(Predicted)
• 密度：
  0.900±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• 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

• 作为产物：
  描述：

  在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,4-双(二苯基膦)丁烷 作用下， 以 乙基苯 为溶剂， 反应 48.0h， 以78%的产率得到2,3-di(n-butyl)-2-cyclopentenone
  参考文献：
  名称：

  Rh-catalyzed reagent-free ring expansion of cyclobutenones and benzocyclobutenones

  摘要：

  报道了一种无试剂的Rh催化的环扩张反应，通过对环丁酮和苯并环丁酮进行C-C键裂解。

  DOI：

  10.1039/c5sc01875g

文献信息

• CuCl-catalyzed reaction of zirconacyclopentenes with oxalyl chloride: a new pathway for the preparation of cyclopentenones
  作者：Chao Chen、Yundong Liu、Chanjuan Xi

  DOI：10.1016/j.tetlet.2009.07.065

  日期：2009.9

  Zirconacyclopentenes, which are easily prepared from alkynes and EtMgBr (or ethylene) and Cp2ZrCl2, reacted with oxalyl chloride in the presence of catalytic amount of CuCl to give cyclopentenones in high yields. The reaction was performed conveniently in one pot from alkynes, EtMgBr, oxalyl chloride, and Cp2ZrCl2.

  容易从炔烃和EtMgBr（或乙烯）和Cp 2 ZrCl 2制备的锆碳环戊烯与草酰氯在催化量的CuCl存在下反应，以高收率得到环戊烯。该反应方便地在一锅中从炔烃，EtMgBr，草酰氯和Cp 2 ZrCl 2进行。
• Zirconium-catalyzed carboalumination of alkynes and enynes as a route to aluminacycles and their conversion to cyclic organic compounds
  作者：Ei-ichi Negishi、Jean-Luc Montchamp、Luigi Anastasia、Arkadij Elizarov、Danièle Choueiry

  DOI：10.1016/s0040-4039(98)00349-9

  日期：1998.4

  Aluminacyclopentenes, obtainable via Zr-catalyzed cyclic carboalumination with Et3Al and alkynes or enynes, can be converted to the corresponding cyclopentenones and alkenylcyclopropanes by treatment with CO2 and BrCH2OCH3, respectively.

  可以通过分别用CO 2和BrCH 2 OCH 3处理，通过Zr催化的Et 3 Al和炔烃或烯炔烃的环状碳铝化反应获得的铝环戊烯转化为相应的环戊烯酮和烯基环丙烷。
• Convenient preparative method of α,β-disubstituted cyclopentenone by zirconium promoted intermolecular coupling of an alkyne, EtMgBr (or ethylene) and CO
  作者：Tamotsu Takahashi、Zhenfeng Xi、Yasushi Nishihara、Shouquan Huo、Kayoko Kasai、Koichiro Aoyagi、Victor Denisov、Ei-ichi Negishi

  DOI：10.1016/s0040-4020(97)00612-1

  日期：1997.7

  Treatment of Cp2ZrCl2 with 2 equiv of EtMgBr in THF, followed by addition of an internal alkyne and subsequent treatment with CO/I-2 gave alpha,beta-disubstituted cyclopentenone in good to high yields. When a conjugated enyne was used as an alkyne component, alpha-alkenyl cyclopentenone was selectively formed in 80-89% yields. In the case of 4,6-decadiyne, alpha-alkynylcyclopentenone was formed in 88% yield. Bridged alkynes such as 1,4-dihexynytbenzene afforded alpha alpha'-bridged cyclopentenone compounds in good yields. (C) 1997 Elsevier Science Ltd.
• Acyl-Lithiation of Olefins:  Formation of Cyclopentenones from 1-Lithio-butadienes and CO
  作者：Qiuling Song、Zhiping Li、Jinglong Chen、Congyang Wang、Zhenfeng Xi

  DOI：10.1021/ol026977l

  日期：2002.12.1

  Intramolecular acyl-lithiation of C=C double bonds proceeds following carbonylation of 1-lithio-1,3-dienes with CO to afford 2- or 3-cyclopentenone derivatives in good to excellent yields after hydrolysis. Addition of electrophiles to the carbonylation reaction mixtures affords various multiply substituted cyclopentenones.
• Rh-catalyzed reagent-free ring expansion of cyclobutenones and benzocyclobutenones
  作者：Peng-hao Chen、Joshua Sieber、Chris H. Senanayake、Guangbin Dong

  DOI：10.1039/c5sc01875g

  日期：——

  A reagent-free Rh-catalyzed ring-expansion reaction via C–C cleavage of cyclobutenones and benzocyclobutenones is reported.

  报道了一种无试剂的Rh催化的环扩张反应，通过对环丁酮和苯并环丁酮进行C-C键裂解。