3-dodecylcyclohexan-1-one | 138695-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-dodecylcyclohexan-1-one
• 英文别名: 3-n-dodecylcyclohexanone；3-Dodecylcyclohexanone
• CAS: 138695-42-8
• 化学式: C₁₈H₃₄O
• mdl: MFCD20177851
• 分子量: 266.467
• InChiKey: HTJVQOQJHPHTBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.944
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 1-十二烯十二碳烯α-十二碳烯α-十二碳烯 在 copper(I) bromide dimethylsulfide complex zirconocene hydrochloride 作用下， 生成 3-dodecylcyclohexan-1-one
  参考文献：
  名称：

  铜催化的有机锆茂的共轭加成。综合和机理研究。

  摘要：

  在3–10 mol％的Cu（l）盐（例如CuBr·S Me 2或CuCN）存在下，烷基锆茂金属很容易添加到α，β-不饱和酮，醛和砜中。反应产率对路易斯酸和碱的存在敏感。在共轭加成过程中可以耐受立体位阻以及广泛的官能团。不饱和氮-酰基恶唑烷酮类对形成新的不对称碳具有高的非对映选择性。所得的烯醇锆可用于醛醇的串联醇醛加成反应。根据所用铜盐的类型，会发生缓慢或快速形成铜镜的现象，但是在光谱学上没有检测到中间的铜物种。因此，提出了一种机理，该机理涉及路易斯酸性的锆茂并烯的烯酮络合，然后烷基取代基的内球转移到螯合的Cu（l）上。

  DOI：

  10.1016/s0040-4020(01)85058-4

文献信息

• <i>N</i>-Ethylpiperidine Hypophosphite Mediated Intermolecular Radical Carbon-Carbon Bond Forming Reaction in Water
  作者：Doo Ok Jang、Dae Hyan Cho

  DOI：10.1055/s-2002-33508

  日期：——

  N-Ethylpiperidine hypophosphite mediated radical addition reactions to electron deficient alkenes in aqueous media have been developed. The reactions afford high isolated yields of addition products without using a large excess of alkenes.

  N-乙基哌啶次磷酸盐介导的自由基加成反应在水性介质中对缺电子烯烃进行了开发。该反应在不使用大量过量烯烃的情况下提供了高分离产率的加成产物。
• Carbon−Carbon Bond Formation by Electrochemical Catalysis in Conductive Microemulsions
  作者：Jianxin Gao、James F. Rusling、De-ling Zhou

  DOI：10.1021/jo9608477

  日期：1996.1.1

  Bicontinuous microemulsions made from oil, water, and surfactants were examined as substitutes for organic solvents in carbon-carbon bond-forming reactions. Conjugated additions of primary alkyl iodides 3a-c to 2-cyclohexen-1-one (4) to give 3-alkyl cyclohexanones 5a-c and cyclization of 2-(4-bromobutyl)-2-cyclohexen-1-one (9) to 1-decalone (10) were mediated by the Co(I)L complex vitamin B-12s generated at carbon cloth electrodes under mild conditions. Reaction of the Co(I)L nucleophile with the alkyl halides gives a Co-alkyl complex. Cleavage of the Co-alkyl complexes by using an electrode potential of -0.85 V (all vs SCE) and irradiation with visible light, or a potential of -1.45 V in the dark, were compared. Addition of the resulting alkyl radicals to the activated double bonds gave comparable yields of 3-alkylcyclohexanone 5a-c (70-80% using -0.85 V + light) and 1-decalone (90%, both cleavage modes) 10 in microemulsions and in DMF. Microemulsions containing hexadecyltrimethylammonium bromide (CTAB) gave remarkable stereoselectivity for the trans isomer of 10, while homogeneous DMF and a sodium dodecylsulfate (SDS) microemulsion gave little stereoselectivity.
• Gas chromatography/electron impact mass spectrometry applied to the differentiation of the positional isomers of long-chainn-alkylcyclohexanones
  作者：J.-F. Rontani、G. Giusti

  DOI：10.1002/oms.1210240910

  日期：1989.9

  AbstractThe influence of n‐butyl group position upon the fragmentation behavior of the three isomeric n‐butylcyclohexanones was studied. The different fragmentation processes are described and have been applied to the differentiation of the positional isomers of long‐chain n‐alkylcyclohexanones. In the case of the 4‐n‐alkyl isomers, an interesting mechanism involving a recyclization is proposed and substantiated by deuterium labelling.
• Conjugate addition reactions of organosamarium species via in situ transmetalation to copper(I) salts
  作者：Michael J. Totleben、Dennis P. Curran、Peter Wipf

  DOI：10.1021/jo00032a027

  日期：1992.3

  Preformed organosamarium species, available by reduction of aryl or alkyl halides with SmI2, were treated with copper(I) salts to effect in situ transmetalation and conjugate addition to enones. In a series of copper(I) salts, CuI.P(OEt)3 gave best results in combination with 2 equiv of organosamarium reagent. This new method allows the multiple formation of carbon-carbon bonds through a combination of radical and cuprate chemistry.
• Copper-catalyzed conjugate additions of organozirconocenes. Synthetic and mechanistic studies.
  作者：Peter Wipf、Wenjing Xu、Jacqueline H. Smitrovich、Roman Lehmann、Luigi M. Venanzi

  DOI：10.1016/s0040-4020(01)85058-4

  日期：1994.2

  broad range of functional groups are tolerated in the conjugate addition process. Unsaturated N-acyl oxazolidinones give high diastereoselectivities for the formation of the new asymmetric carbon. The resulting zirconium enolates can be used for tandem aldol addition reactions to aldehydes. Depending on the type of copper salt used, slow or fast formation of copper mirror occurs, but no intermediate

  在3–10 mol％的Cu（l）盐（例如CuBr·S Me 2或CuCN）存在下，烷基锆茂金属很容易添加到α，β-不饱和酮，醛和砜中。反应产率对路易斯酸和碱的存在敏感。在共轭加成过程中可以耐受立体位阻以及广泛的官能团。不饱和氮-酰基恶唑烷酮类对形成新的不对称碳具有高的非对映选择性。所得的烯醇锆可用于醛醇的串联醇醛加成反应。根据所用铜盐的类型，会发生缓慢或快速形成铜镜的现象，但是在光谱学上没有检测到中间的铜物种。因此，提出了一种机理，该机理涉及路易斯酸性的锆茂并烯的烯酮络合，然后烷基取代基的内球转移到螯合的Cu（l）上。