1-(1-hydroxy-cyclohexyl)-2,2-dimethyl-propan-1-one | 103648-08-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1-hydroxy-cyclohexyl)-2,2-dimethyl-propan-1-one
• 英文别名: 1-(1-Hydroxy-cyclohexyl)-2,2-dimethyl-propan-1-on；1-Propanone, 1-(1-hydroxycyclohexyl)-2,2-dimethyl-；1-(1-hydroxycyclohexyl)-2,2-dimethylpropan-1-one
• CAS: 103648-08-4
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: VRNHRIBENYNKRN-UHFFFAOYSA-N

物化性质

• 沸点：
  274.9±23.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环己酮氰醇 生成 1-(1-hydroxy-cyclohexyl)-2,2-dimethyl-propan-1-one
  参考文献：
  名称：

  Elphimoff-Felkin et al., Bulletin de la Societe Chimique de France, 1958, p. 522,530

  摘要：

  DOI：

文献信息

• High yield acyl anion transfer reactions: nucleophilic acylation of aldehydes
  作者：Dietmar Seyferth、Robert M. Weinstein、Wei-Liang Wang、Richard C. Hui

  DOI：10.1016/s0040-4039(01)99807-7

  日期：1983.1

  Aldehydes may be acylated to give R'CH(ON)C(O)R in good yield by the RLi/CO in situ procedure at very low temperatures. Examples are given of ketone acylations which demonstrate the advantages of 1:1 RLi/substrate stoichiometry and the use of lower (−135°C) temperature.

  可以通过在非常低的温度下通过RLi / CO原位程序将醛酰化，从而以高收率得到R'CH（ON）C（O）R。给出了酮酰化反应的实例，这些实例证明了1：1 RLi /底物化学计量比的优势以及使用较低温度（-135°C）的优势。
• Imidoyl chlorides as starting materials for the preparation of masked acyllithium intermediates: synthetic applications
  作者：Emma Alonso、Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4020(98)83054-8

  日期：1998.9

  The lithiation of several imidoyl chlorides 5, catalysed by substoichiometric amounts of naphthalene, followed by reaction with different electrophiles gives, after hydrolysis, the corresponding imine derivatives 6 and 9 or amines 7, depending on the reaction conditions. The imine derivatives are easily converted into the corresponding ketones by treatment either with dilute hydrochloric acid, for

  通过亚化学计量的萘催化几种亚氨基酰氯5的锂化，然后与不同的亲电试剂反应，在水解后，根据反应条件，得到相应的亚胺衍生物6和9或胺7。通过用稀盐酸（对于N-芳基衍生物）或用硅胶（对于N-烷基衍生物）处理，将亚胺衍生物容易地转化成相应的酮。得到的羟基亚胺与LiAlH 4反应，得到相应的1，2-氨基醇，为单一的非对映异构体。当亚胺部分在原位时，发现相同的结果用锂还原。得到的1,2-氨基醇很容易转变成相应的1,3-恶唑烷11通过与反应段在酸性催化下-甲醛。
• Imidoyllithiums: Masked acyllithium reagents
  作者：Emma Alonso、Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4039(97)10357-4

  日期：1997.12

  imines 3. For starting material 1a is necessary to filter off the excess of lithium at the end of the lithiation step in order to get compounds 3, without filtration amines 4 are the reaction products isolated. Hydrolysis of compounds 3 either during chromatographic purification or by acidic hydrolysis (2 N HCl, THF) gives the expected functionalised ketones 5.

  氯亚胺1与过量的锂粉和催化量的萘（4摩尔％）在-78°C的THF中反应，生成相应的亚胺基锂中间体2，该中间体通过用不同的亲电试剂处理[Pr i CHO，Bu t CHO，n -C 5 H 11 CHO，PhCHO，Et 2 CO，（CH 2）5 CO，EtCOCl，MeOCSCl，n -C 7 H 15 CON（Me）OMe]在-78至20°C下进行最终水解水提供功能化的亚胺3。用于原料1a为了获得化合物3，必须在锂化步骤结束时过滤掉过量的锂，而无需过滤就分离出了胺4。化合物3在色谱纯化过程中或通过酸性水解（2 N HCl，THF）进行水解，得到了预期的官能化酮5。
• Synthesis of .alpha.-hydroxy ketones by direct, low-temperature, in situ nucleophilic acylation of aldehydes and ketones by acyllithium reagents
  作者：Dietmar Seyferth、Robert M. Weinstein、Richard C. Hui、Wei Liang Wang、Colin M. Archer

  DOI：10.1021/jo00047a014

  日期：1992.10

  The reaction of n-, sec-, and tert-butyllithium with CO at atmospheric pressure at -110 and -135-degrees-C in the appropriate solvent system in the presence of ketones and aldehydes generates the acyllithium, RC(O)Li, which reacts with the carbonyl compound to give the alpha-hydroxy ketone, generally in good yield. Reactions with aldehydes are limited in scope, working well with the t-BuLi-derived acyllithium reagents, but not with n-BuC(O)Li.
• SEYFERTH, D.;WEINSTEIN, R. M.;WANG, WEI-LIANG;HUI, R. C., TETRAHEDRON LETT., 1983, 24, N 45, 4907-4910
  作者：SEYFERTH, D.、WEINSTEIN, R. M.、WANG, WEI-LIANG、HUI, R. C.

  DOI：——

  日期：——