1-Formyl-1-(3-oxobutyl)cyclohexane | 30834-43-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Formyl-1-(3-oxobutyl)cyclohexane
• 英文别名: 1-(3-Oxobutyl)cyclohexane-1-carbaldehyde
• CAS: 30834-43-6
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: KRVKEXHUJQGIAT-UHFFFAOYSA-N

物化性质

• 沸点：
  273.2±13.0 °C(Predicted)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Formyl-1-(3-oxobutyl)cyclohexane 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 螺[5.5]-3-十一酮
  参考文献：
  名称：

  Christol,H. et al., Bulletin de la Societe Chimique de France, 1970, p. 4468 - 4471

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Formyl-1-(3-butenyl)cyclohexane 在 copper diacetate 、 水 、 氧气 、 palladium dichloride 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以62%的产率得到1-Formyl-1-(3-oxobutyl)cyclohexane
  参考文献：
  名称：

  亚化学计量的乙酸铜可方便地进行Wacker氧化

  摘要：

  描述了使用亚化学计量的量的Cu（OAc）2作为氧化还原穿梭试剂将末端烯烃的Wacker氧化修饰为甲基酮的方法。尽管减少了铜盐的含量，但是改进的方法通常还是高产率的并且方便。重要的是，在有问题的情况下，该条件抑制了在含丙酮化物的底物（+）- 5的氧化过程中的酸性水解。

  DOI：

  10.1016/s0040-4039(98)01992-3

文献信息

• 1,5-Dicarbonyl compounds
  作者：P. Duhamel、L. Hennequin、J.M. Poirier、G. Tavel、C. Vottero

  DOI：10.1016/s0040-4020(01)82058-5

  日期：1986.1

  In this report, a general method for the preparation of 1,5-dicarbonyl compounds and six membered ring annelation is described. This method involves the reaction of hemiacetal vinylogs 1 with enol ethers 2 or 3 in the presence of a Lewis acid. This reaction was successfully applied to the enol ethers of α and α,α'-hindered ketones such as 2,2,6-trimethyl cyclohexanone. α-Cyperone and 6-epi-α-cyperone

  在此报告中，描述了制备1,5-二羰基化合物和六元环成环的一般方法。该方法涉及在路易斯酸存在下半缩醛乙烯基酯1与烯醇醚2或3的反应。该反应成功地应用于α和α，α'受阻的酮的烯醇醚，例如2,2,6-三甲基环己酮。使用该方法获得α-Cyperone和6-epi-α-Cyperone。
• NMR-based molecular ruler for determining the depth of intercalants within the lipid bilayer
  作者：Yael Cohen、Efrat Bodner、Michal Richman、Michal Afri、Aryeh A. Frimer

  DOI：10.1016/j.chemphyslip.2008.07.004

  日期：2008.10

  The development of "molecular rulers" would allow one to quantitatively locate intercalants within the liposomal bilayer. To this end, we have attempted to correlate the C-13 NMR chemical shift of a polarizable "reporter" carbon (e.g., carbonyl) of the intercalant-with the E-T(30) polarity it experiences, and with its Angstrom distance from the interface. This requires families of molecules with the same two "reporter carbons" separated by a fixed distance, residing at various depths/polarities within the bilayer. The families studied included 4,4-dialkylcyclohexa-2,5-dienones 1, benzenediacetic esters 15, benzenedipropionic esters 17, 4-alkoxybenzaldehydes 19 and methyl 4-alkoxybenzoates 22. These compounds possessed the following characteristics: (1) a planar backbone; (2) polar/hydrophilic "head" groups: (3) modular hydrophobic tails; (4) large changes in the C-13 NMR chemical shift (Delta delta) of the reporter atoms with sol- vent polarity. These studies revealed a fifth requirement, namely: (5) the reporter carbons must not be strongly conjugated, lest it reflect the charge build-up at another site within the conjugated system. (C) 2008 Elsevier Ireland Ltd. All rights reserved.
• Geminal acylation-alkylation at a carbonyl carbon via regiospecifically generated metalloenamines
  作者：Stephen F. Martin、Gerald W. Phillips、Thomas A. Puckette、John A. Colapret

  DOI：10.1021/ja00538a027

  日期：1980.8
• Neighboring group participation in Lewis acid-promoted [3 + 4] and [3 + 5] annulations. The stereocontrolled synthesis of tricyclic ethers
  作者：Gary A. Molander、Kimberly O. Cameron

  DOI：10.1021/jo00074a018

  日期：1993.10

  A variety of 1,4- and 1,5-keto aldehydes derived from cycloalkanes are coupled with the bis(trimethylsilyl) enol ether of methyl acetoacetate in the presence of either TMSOTf or TrSbCl6 to generate tricyclic ethers. The reactions proceed with excellent regiochemical control by a mechanism involving neighboring group participation. This mechanism involves initial formation of a bicyclic oxocarbenium ion intermediate from the keto aldehyde substrates. The geometries of selected bicyclic intermediates have been optimized using the AM1 method allowing successful prediction of the stereochemical outcomes in the cyclization in most cases. Epimerization of alpha-chiral keto aldehyde substrates does not appear to occur in these Lewis acid-promoted annulation reactions.
• MARTIN S. F.; PHILLIPS G. W.; PUCKETTE T. A.; COLAPRET J. A., J. AMER. CHEM. SOC., 1980, 102, NO 18, 5866-5872
  作者：MARTIN S. F.、 PHILLIPS G. W.、 PUCKETTE T. A.、 COLAPRET J. A.

  DOI：——

  日期：——