3-(n-octyl)cyclobutanone | 160002-82-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(n-octyl)cyclobutanone
• 英文别名: 3-n-octylcyclobutanone；3-octylcyclobutanone；3-octyl cyclobutanone；Cyclobutanone, 3-octyl-；3-octylcyclobutan-1-one
• CAS: 160002-82-4
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: DCXUUFRIRJVXJX-UHFFFAOYSA-N

物化性质

• 沸点：
  249.5±8.0 °C(Predicted)
• 密度：
  0.893±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  3-(n-octyl)cyclobutanone 在 氧气 、 特戊醛 作用下， 以77%的产率得到δ-dodecanolactone
  参考文献：
  名称：

  Enantioselective Metal-catalyzed Baeyer-Villiger Oxidation of Cyclobutanones

  摘要：

  光学活性内酯是通过金属催化的有氧氧化前手性环丁酮获得的。从3-单取代底物出发，获得了具有中等对映选择性（高达47% ee）的内酯。凯利的三环酮8提供了相应的内酯，具有91%的对映体过量。

  DOI：

  10.1055/s-1997-977
• 作为产物：
  描述：

  正癸烯 在 溶剂黄146 、 锌 作用下， 生成 3-(n-octyl)cyclobutanone
  参考文献：
  名称：

  Two-carbon ring expansion of cyclobutanone skeletons by nickel-catalyzed intermolecular alkyne insertion

  摘要：

  The reaction of cyclobutanone with an alkyne in the presence of a nickel(0) catalyst formally achieves intermolecular alkyne insertion between the carbonyl carbon and the a-carbon of a cyclobutanone, providing a six-membered carbocyclic skeleton. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.118

文献信息

• Enantioselective Baeyer–Villiger Oxidation Catalyzed by Palladium(II) Complexes with Chiral <i>P,N</i>-Ligands
  作者：Andrei V. Malkov、Frédéric Friscourt、Mark Bell、Martin E. Swarbrick、Pavel Kočovský

  DOI：10.1021/jo800246g

  日期：2008.6.1

  Asymmetric Baeyer–Villiger reaction of symmetrical cyclobutanones 1a−j with urea−hydrogen peroxide (UHP) can be catalyzed by a complex of Pd(II) and the new terpene-derived P,N-ligand 7. The resulting lactones 2a−j were obtained in high yields and with good enantioselectivity (≤81% ee).

  对称cyclobutanones的不对称拜尔-维利格反应1A - Ĵ与脲-过氧化氢（UHP）可以通过一个复杂的Pd（II）和新的萜烯衍生的催化P，ñ -配体7。得到的内酯2a - j以高收率和良好的对映选择性（≤81％ee）获得。
• Eight-Membered Ring Construction by [4 + 2 + 2] Annulation Involving β-Carbon Elimination
  作者：Masahiro Murakami、Shinji Ashida、Takanori Matsuda

  DOI：10.1021/ja0552895

  日期：2006.2.1

  Cyclobutanones underwent a formal [4 + 2 + 2] annulation reaction with 1,6- and 1,7-diynes in the presence of nickel(0) catalysts to provide bicyclic eight-membered ring ketones. The annulation reaction proceeds through a ring-expansion of oxanickelacycloheptadiene via beta-carbon elimination to form a nine-membered nickelacycle. This reaction employing cyclobutanones as a C4 unit constructs cyclooctadienone

  环丁酮在镍 (0) 催化剂存在下与 1,6- 和 1,7-二炔进行正式的 [4 + 2 + 2] 环化反应，以提供双环八元环酮。环化反应通过氧杂镍环庚二烯通过β-碳消除进行扩环以形成九元镍环。这种使用环丁酮作为 C4 单元的反应在一个合成步骤中构建了环辛二烯酮核。
• Nickel-Catalyzed [4+2+2]-Type Annulation Reaction of Cyclobutanones with Diynes and Enynes
  作者：Shinji Ashida、Masahiro Murakami

  DOI：10.1246/bcsj.81.885

  日期：2008.7.15

  In the presence of a nickel(0) catalyst, cyclobutanones reacted with diynes to produce bicyclic eight-membered ring ketones. Cyclobutanones acted as a C4 unit in the formal [4+2+2]-type annulation reaction, which proceeded through a ring-expansion of a spirocyclic seven-membered oxanickelacycle to a nine-membered nickelacycle via β-carbon elimination. A similar annulation reaction was also examined with enynes.

  在镍(0)催化剂的存在下，环丁酮与二炔反应生成双环八元环酮。环丁酮在这种形式的[4+2+2]型环加成反应中充当C4单元，该反应通过螺环七元氧镍杂环的环扩张过程，通过β-碳消除转化为九元镍杂环。还研究了类似的与烯炔的环加成反应。
• [EN] AMPHIPHILIC CYCLOBUTENES AND CYCLOBUTANES<br/>[FR] CYCLOBUTÈNES ET CYCLOBUTANES AMPHIPHILES
  申请人：NUTECH VENTURES

  公开号：WO2013181155A1

  公开（公告）日：2013-12-05

  This disclosure relates to amphiphilic compounds containing a cyclobutene or cyclobutane moiety. In some embodiments, the compounds are useful for treating infection by Mycobacterium such as Mycobacterium tuberculosis. Cyclobutene containing compounds are also useful as monomers in the preparation of amphiphilic polymers.

  这项披露涉及含有环丁烯或环丁烷基团的两性化合物。在某些实施例中，这些化合物可用于治疗结核分枝杆菌等分枝杆菌感染。含环丁烯的化合物还可用作两性聚合物的单体。
• Ligand effects in aluminium-catalyzed asymmetric Baeyer–Villiger reactions
  作者：Jean-Cédric Frison、Chiara Palazzi、Carsten Bolm

  DOI：10.1016/j.tet.2005.12.080

  日期：2006.7

  Asymmetric Baeyer–Villiger oxidations of racemic and prochiral cyclobutanones can be performed with chiral aluminium-based Lewis acids resulting in products with good enantioselectivities in high yields. By employing substituted BINOL derivatives as ligands, remarkable catalyst efficiencies have been achieved and γ-butyrolactones with up to 84% ee were obtained. The relation between the electronic

  外消旋和手性环丁酮的不对称Baeyer-Villiger氧化反应可以用基于铝的手性路易斯酸进行，从而产生具有高对映选择性的产品。通过使用取代的BINOL衍生物作为配体，获得了显着的催化剂效率，并获得了ee高达84％的γ-丁内酯。已经研究了配体的电子性质与反应的对映选择性之间的关系，从而使人们更好地理解了在铝催化的氧化转化中实现良好对映选择性的要求。