4,4-(ethylenedioxy)-2-(hydroxyphenylmethyl)cyclohexanone | 1181812-21-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4-(ethylenedioxy)-2-(hydroxyphenylmethyl)cyclohexanone
• 英文别名: 4,4-(ethylenedioxy)-2-(hydroxyphenylmethyl)cyclohexan-1-one；(7S)-7-[(R)-hydroxy(phenyl)methyl]-1,4-dioxaspiro[4.5]decan-8-one
• CAS: 1181812-21-4
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: PSCJLWYHFDEEMT-OCCSQVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 、 苯甲醛 在 四氯化硅 、 N,N-二异丙基乙胺 、 2,2'-双(二苯基氧膦)-1,1'-联萘 作用下， 以 丙腈 为溶剂， 反应 6.0h， 生成 4,4-(ethylenedioxy)-2-(hydroxyphenylmethyl)cyclohexanone 、 4,4-(ethylenedioxy)-2-(hydroxyphenylmethyl)cyclohexanone
  参考文献：
  名称：

  手性氧化膦作为有机催化剂促进的新型对映选择性直接羟醛型反应

  摘要：

  手性氧化膦以高的立体选择性成功催化了环己酮衍生物和苯甲醛衍生物的直接羟醛型反应。反应机理涉及三氯甲硅烷基烯醇醚的原位形成。本反应可以扩展到两个醛之间的交叉-羟醛反应。

  DOI：

  10.1016/j.tetlet.2009.05.065

文献信息

• Biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol reactions
  作者：Sergio Rossi、Maurizio Benaglia、Andrea Genoni、Tiziana Benincori、Giuseppe Celentano

  DOI：10.1016/j.tet.2010.11.009

  日期：2011.1

  A highly stereoselective direct aldol condensation of ketones to aromatic aldehydes was realized; the trichlorosilyl enolether generated in situ in the presence of tetrachlorosilane is activated by catalytic amounts of an enantiomerically pure biheteroaromatic phosphine oxide to react with aldehydes, coordinated as well as activated by the chiral cationic hypervalent silicon species. This Lewis acid-mediated Lewis base-catalyzed transformation allowed, starting from two carbonyl compounds, to directly synthesize beta-hydroxy ketones generally with high anti stereoselectivity and up to 93% ee for the anti isomer. (C) 2010 Elsevier Ltd. All rights reserved.
• Trichlorosilyl triflate for enantioselective direct-type aldol reaction with chiral phosphine oxide
  作者：Shunsuke Kotani、Shohei Aoki、Masaharu Sugiura、Makoto Nakajima

  DOI：10.1016/j.tetlet.2011.03.095

  日期：2011.6

  Trichlorosilyl triflate, in the presence of a chiral Lewis base catalyst, provides an effective method for the enantioselective direct-type aldol reaction of aldehydes and ketones. A chiral Lewis base induces both the production and activation of trichlorosilyl enol ether, yielding an aldol product in good yield and with high diastereo- and enantioselectivities. (C) 2011 Elsevier Ltd. All rights reserved.
• Novel enantioselective direct aldol-type reaction promoted by a chiral phosphine oxide as an organocatalyst
  作者：Shunsuke Kotani、Yasushi Shimoda、Masaharu Sugiura、Makoto Nakajima

  DOI：10.1016/j.tetlet.2009.05.065

  日期：2009.8

  Chiral phosphine oxide successfully catalyzed the direct aldol-type reactions of cyclohexanone derivatives and benzaldehyde derivatives in high stereoselectivities. The reaction mechanism involves the in situ formation of trichlorosilyl enol ethers. The present reaction could be extended to the cross-aldol reactions between two aldehydes.

  手性氧化膦以高的立体选择性成功催化了环己酮衍生物和苯甲醛衍生物的直接羟醛型反应。反应机理涉及三氯甲硅烷基烯醇醚的原位形成。本反应可以扩展到两个醛之间的交叉-羟醛反应。