2,4-dimethylcyclobutanone | 43042-67-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-dimethylcyclobutanone
• 英文别名: 2,4-Dimethyl-cyclobutanon；2.4-Dimethyl-cyclobutanon；2,4-Dimethylcyclobutanon；2.4-Dimethylcyclobutanon；2,4-dimethylcyclobutan-1-one
• CAS: 43042-67-7
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: DJYHNXPUOPESJN-UHFFFAOYSA-N

物化性质

• 沸点：
  131.8±8.0 °C(Predicted)
• 密度：
  0.913±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  2,4-dimethylcyclobutanone 、 九氟丁基磺酸酐 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 2,4-dimethyl-1-cyclobutenyl nonaflate
  参考文献：
  名称：

  Vinyl cations. 42. Synthesis and solvolysis of substituted 1-cyclobutenyl nonaflates

  摘要：

  DOI：

  10.1021/ja00304a034
• 作为产物：
  描述：

  二溴戊烷 在 硫酸 、 sodium hydride 、 potassium carbonate 作用下， 以 环丁砜 、 乙醚 、 水 、 二甲基亚砜 为溶剂， 生成 2,4-dimethylcyclobutanone
  参考文献：
  名称：

  Vinyl cations. 42. Synthesis and solvolysis of substituted 1-cyclobutenyl nonaflates

  摘要：

  DOI：

  10.1021/ja00304a034

文献信息

• Ripoll,J.-L.; Conia,J.-M., Bulletin de la Societe Chimique de France, 1965, p. 2755 - 2762
  作者：Ripoll,J.-L.、Conia,J.-M.

  DOI：——

  日期：——
• Preparation and Structure Investigations of Simple Bicyclo[1.1.0]butanones
  作者：A. Rauk、T. S. Sorensen、F. Sun

  DOI：10.1021/ja00121a009

  日期：1995.4

  Four 1,3-dialkyl-substituted bicyclo[1.1.0]butanones have been prepared, All have been completely characterized by H-1 and C-13 NMR spectroscopy, but O-17 NMR proved to be particularly diagnostic. The di-t-Bu 4 and di-tert-amyl 5 members can be obtained in the condensed phase by working quickly and at subambient temperatures, but attempts to obtain X-ray quality crystals have not been successful. The synthetic procedure involves a very rapid and efficient 1,3-elimination of two bromine atoms from 1,3-dibromocyclobutan-2-ones using the salt PPN+Cr(CO)(4)NO-. This reaction is particularly well-suited for exploratory in situ low-temperature MMR experiments, Molecular orbital calculations show these ketones to have the typical bent bicyclobutane structure, but the central C1-C3 bond is very long and the carbonyl carbon is distinctly nonplanar. Both of these features can be attributed to a strong interaction of the C1-C3 ''bond'' with the carbonyl group, and several qualitative orbital interaction schemes are presented to show that bicyclobutanones have on one hand some oxyallyl character and, on the other, some similarities with the bonding in esters. Nucleophiles react with bicyclobutanones in a nonconcerted process to add across the C1-C3 bond.
• WASSERMAN H. H.; HERN M. J.; COCHOY R. E., J. ORG. CHEM., 1980, 45, NO 14, 2874-2880,
  作者：WASSERMAN H. H.、 HERN M. J.、 COCHOY R. E.

  DOI：——

  日期：——
• HANACK, M.;AUCHTER, G., J. AMER. CHEM. SOC., 1985, 107, N 18, 5238-5245
  作者：HANACK, M.、AUCHTER, G.

  DOI：——

  日期：——
• Vinyl cations. 42. Synthesis and solvolysis of substituted 1-cyclobutenyl nonaflates
  作者：Michael Hanack、Gerhard Auchter

  DOI：10.1021/ja00304a034

  日期：1985.9