2-allyl-2-(phenylsulfonyl)cyclohexanone | 139408-56-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-allyl-2-(phenylsulfonyl)cyclohexanone
• 英文别名: 2-(Benzenesulfonyl)-2-prop-2-enylcyclohexan-1-one
• CAS: 139408-56-3
• 化学式: C₁₅H₁₈O₃S
• 分子量: 278.372
• InChiKey: FXTCIFUFMXOBBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-allyl-2-(phenylsulfonyl)cyclohexanone 在 sodium hydroxide 、 十六烷基三甲基氯化铵 作用下， 以64%的产率得到6-Benzenesulfonyl-non-8-enoic acid
  参考文献：
  名称：

  通过砜的CC键裂变：环状β-酮基苯基砜的新环裂解

  摘要：

  β-酮砜与2N NaOH在70°C下在水性介质中和十六烷基三甲基氯化铵（CTACl）的存在下反应，在羰基和带有砜的碳之间产生CC键裂变。

  DOI：

  10.1016/s0040-4020(97)00417-1
• 作为产物：
  描述：

  2-(phenylsulphonyl)cyclohexanone 、 3-溴丙烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 2-allyl-2-(phenylsulfonyl)cyclohexanone
  参考文献：
  名称：

  Reluctant Cross-Metathesis Reactions: The Highly Beneficial Effect of Microwave Irradiation

  摘要：

  微波辐射相对于传统热条件的有益效果通过一系列比较的交叉转烯反应得以证明。

  DOI：

  10.1055/s-2007-983825

文献信息

• pH optimization of nucleophilic reactions in water
  作者：J. F. King、R. Rathore、J. Y. L. Lam、Z. R. Guo、D. F. Klassen

  DOI：10.1021/ja00034a040

  日期：1992.4

  We present a way of prescribing the pH for a reaction so as to obtain either (a) maximum yield in competition with hydrolysis or (b) selective reaction at either of two sites in such nucleophile-electrophile reactions as C-alkylation of acidic ketones and the acylation and sulfonylation of amines. First, we derive the following general equation for pH(max), the pH giving the highest yield of the product (P) of the reaction of a nucleophile (Nu) with a hydrolyzable electrophile (E) in water: pH(max) = 1/2[log (k(w)/k(OH)) + pK(w) + pK(a)] (k(w) and k(OH) refer to the water- and hydroxide-promoted hydrolyses of E, K(w) is the autoprotolysis constant of water, and K(a) is the acid dissociation constant of NuH+, the conjugate acid of Nu). pH(max) thus depends on a property of E (namely, k(w)/k(OH)) and a property of Nu (the pK(a) of NuH+), but not on the rate constant for the reaction of E with Nu or the concentration of Nu. We then deduce analogous approximate equations for maximum selectivity for reaction at either of two nucleophilic sites, specifically, equations giving pH(xmax) and pH(ymax), the pH values for the maximum yields of the respective products (P(x) and P(y)) of the reactions of E with the two nucleophiles. We find that (a) pH-yield profiles calculated from the equations concur with observed yields for reactions under pseudo-first-order conditions and (b) preparative experiments at the estimated pH values give good to excellent yields of clean products and high selectivity in both the C-alkylation and Schotten-Baumann reactions.
• Reluctant Cross-Metathesis Reactions: The Highly Beneficial Effect of Microwave Irradiation
  作者：Yoann Coquerel、Jean Rodriguez、Antoine Michaut、Thomas Boddaert

  DOI：10.1055/s-2007-983825

  日期：2007.9

  The beneficial effect of microwave irradiation versus classical thermal conditions is demonstrated through a series of comparative cross-metathesis reactions.

  微波辐射相对于传统热条件的有益效果通过一系列比较的交叉转烯反应得以证明。
• CC bond fission via sulphones: A new ring cleavage of cyclic β-keto phenylsulphones
  作者：Roberto Ballini、Giovanna Bosica、Tiziana Mecozzi

  DOI：10.1016/s0040-4020(97)00417-1

  日期：1997.5

  Reaction of β-keto sulphones with 2N NaOH, at 70°C, in aqueous media and in presence of cetyltrimethylammonium chloride (CTACl), produces the CC bond fission between the carbonyl group and the carbon bearing the sulphone.

  β-酮砜与2N NaOH在70°C下在水性介质中和十六烷基三甲基氯化铵（CTACl）的存在下反应，在羰基和带有砜的碳之间产生CC键裂变。