2.4-Diisopropyl-cyclobutanon | 16596-60-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2.4-Diisopropyl-cyclobutanon
• 英文别名: 1,3-Diisopropyl-cyclobutanon-(2)；2,4-Di(propan-2-yl)cyclobutan-1-one
• CAS: 16596-60-4
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: SDQBABYMXQGIKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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-Diisopropyl-cyclobutanon 在 PPN(1+)*Cr(CO)4NO(1-) 、 氢溴酸 、 溴 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1,3-二异丙基双环[1.1.0]丁烷-2-酮
  参考文献：
  名称：

  Preparation and Structure Investigations of Simple Bicyclo[1.1.0]butanones

  摘要：

  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.

  DOI：

  10.1021/ja00121a009
• 作为产物：
  描述：

  di-2,4-(1-methylidene)cyclobutanone 在 镍 氢气 作用下， 生成 2.4-Diisopropyl-cyclobutanon
  参考文献：
  名称：

  Conia,J.-M.; Sandre,J.-P., Bulletin de la Societe Chimique de France, 1963, p. 744 - 752

  摘要：

  DOI：

文献信息

• Branched amides of L-aspartyl-D-amino acid dipeptides and compositions thereof
  申请人：PFIZER INC.

  公开号：EP0034876B1

  公开（公告）日：1984-08-29
• US4399163A
  申请人：——

  公开号：US4399163A

  公开（公告）日：1983-08-16
• US4411925A
  申请人：——

  公开号：US4411925A

  公开（公告）日：1983-10-25
• US4454328A
  申请人：——

  公开号：US4454328A

  公开（公告）日：1984-06-12
• US4517379A
  申请人：——

  公开号：US4517379A

  公开（公告）日：1985-05-14