3,3-Diethylcyclobutanone | 215957-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-Diethylcyclobutanone
• 英文别名: 3,3-diethylcyclobutan-1-one
• CAS: 215957-65-6
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: GJNBYMJQVVJXDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  3,3-Diethylcyclobutanone 在 sodium hydride 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 、 甲苯 、 mineral oil 为溶剂， 反应 3.08h， 生成 3-(4,4-diethyl-1-methyl-2-oxocyclopentyl)propanenitrile
  参考文献：
  名称：

  Elimination versus Ring Opening: A Convergent Route to Alkylidene-Cyclobutanes

  摘要：

  Functionalized alkylidene-cyclobutanes have been prepared from 2-fluoropyridinyl-6-oxy precursors derived from vinyl cyclobutanols by a radical addition elimination process. A wide range of functional groups is tolerated, and the alkylidene-cyclobutanes can be further elaborated Into cyclopentanones. The limitation of this approach resides in the competition with opening of the cyclobutane ring.

  DOI：

  10.1021/ol202798r
• 作为产物：
  描述：

  2-乙基-1-丁烯 在 锌 作用下， 以 乙醚 、 溶剂黄146 为溶剂， 反应 1.83h， 生成 3,3-Diethylcyclobutanone
  参考文献：
  名称：

  Adler, Roger W.; Allen, Paul R.; Anderson, Kevin R., Journal of the Chemical Society. Perkin transactions II, 1998, # 10, p. 2083 - 2108

  摘要：

  DOI：

文献信息

• 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。
• Oxyallyl cation promoted dearomative semipinacol rearrangement: a facile stereodivergent synthesis of spiro-indolines with contiguous quaternary centers
  作者：Yu-Yang Xie、Yun-Peng Wang、Xiao-Jing Zhao、Ai-Fang Wang、Zhi-Min Chen、Yong-Qiang Tu

  DOI：10.1039/d1cc02033a

  日期：——

  indole-type allylic alcohols was disclosed for the stereodivergent synthesis of spiro-indolines. A variety of spiro-indolines were obtained with moderate to good yields. Three contiguous stereocenters, two of which are vicinal quaternary centers, were effectively formed with good diastereoselectivity. It is worth noting that two diastereoisomers of rearranged products can be readily achieved by easily regulating

  公开了一种新的氧烯丙基阳离子促进吲哚型烯丙醇的半频哪醇重排，用于螺二氢吲哚的立体发散合成。以中等至良好的收率获得了多种螺-二氢吲哚。三个连续的立体中心，其中两个是相邻的四元中心，有效地形成并具有良好的非对映选择性。值得注意的是，通过轻松调节反应条件，可以很容易地实现重排产物的两种非对映异构体。该方法可为天然吲哚生物碱的合成提供一条适用的途径。
• Palladium-Catalyzed Asymmetric Ring Expansion of Allenylcyclobutanols:  An Asymmetric Wagner−Meerwein Shift
  作者：Barry M. Trost、Jia Xie

  DOI：10.1021/ja0602501

  日期：2006.5.1

  In this study, we developed a palladium-catalyzed atom economic asymmetric Wagner-Meerwein shift of allenylcyclobutanol substrates. It is an excellent method for creating functionalized cyclopentanones with an alpha-chiral O-tertiary center by ring expansion of allenylcyclobutanols. This reaction was initiated by hydropalladation and afforded excellent enantioselectivity as well as atom economy. This

  在这项研究中，我们开发了钯催化的烯基环丁醇底物的原子经济不对称 Wagner-Meerwein 位移。它是通过烯基环丁醇的扩环来产生具有α-手性O-叔中心的官能化环戊酮的极好方法。该反应由氢化钯反应引发，并提供优异的对映选择性和原子经济性。该方法提供了合成天然产物的有效途径，例如 trans-kumausyne 家族、螺环系统。此外，我们通过使用 3-单取代的烯丙基环丁醇同时获得了优异的非对映选择性和对映选择性。
• Nickel-Catalyzed Intermolecular Alkyne Insertion into Cyclobutanones
  作者：Masahiro Murakami、Shinji Ashida、Takanori Matsuda

  DOI：10.1021/ja050674f

  日期：2005.5.1

  Cyclobutanones reacted with alkynes in the presence of nickel(0) catalysts to produce cyclohexenones. Oxidative cyclization of the carbonyl group of the cyclobutanone and the alkyne with the nickel(0) was followed by beta-carbon elimination from the resulting oxanickelacyclopentene and subsequent reductive elimination. This reaction achieves a formal alkyne insertion between the carbonyl carbon and

  环丁酮在镍 (0) 催化剂存在下与炔烃反应生成环己烯酮。环丁酮和炔烃的羰基与镍 (0) 的氧化环化之后，从所得氧杂镍环戊烯中消除 β-碳，然后进行还原消除。该反应在羰基碳和α-碳之间实现了正式的炔烃插入，提供了一个六元碳环骨架。