(S,S)-2-[1-hydroxy-(1-pentafluorophenyl)-methyl]-cyclohexanone

• 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: (S,S)-2-[1-hydroxy-(1-pentafluorophenyl)-methyl]-cyclohexanone
• 英文别名: (S)-2-[(S)-hydroxy(perfluorophenyl)methyl]cyclohexanone；(2S)-2-[(S)-hydroxy-(2,3,4,5,6-pentafluorophenyl)methyl]cyclohexan-1-one
• 化学式: C₁₃H₁₁F₅O₂
• 分子量: 294.221
• InChiKey: RVWBCXZSQOZTLA-GMAUIZIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  环己酮 、 五氟苯甲醛 在 1,1'-binaphthyl-2,2'-diamine-based (S)-prolineamide 硬脂酸 作用下， 以 水 为溶剂， 反应 12.0h， 生成 (S,S)-2-[1-hydroxy-(1-pentafluorophenyl)-methyl]-cyclohexanone 、 2-(hydroxy(perfluorophenyl)methyl)cyclohexan-1-one
  参考文献：
  名称：

  Enantioselective Direct Aldol Reaction “on Water” Promoted by Chiral Organic Catalysts

  摘要：

  1,1'-Binaphthyl-2,2'-diamine-based (S)-prolinamides in the presence of stearic acid were able to promote the direct aldol condensation of cyclohexanone and other ketones with different aldehydes in the presence of a massive amount of water in very good yields, high diastereoselectivity, and up to 99% ee. The behavior of both C-2- and C-1-symmetric catalysts in combination with different additives was investigated, and a preliminary experiment of recovering and recycling of the catalytic system was also attempted.

  DOI：

  10.1021/ol070002p

文献信息

• Evaluation of 6-APA as a New Organocatalyst for a Direct Cross-Aldol Reaction
  作者：Enrico Emer、Paola Galletti、Daria Giacomini

  DOI：10.1002/ejoc.200900181

  日期：2009.7

  6-Aminopenicillanic acid (6-APA) and two of its derivatives, 6-APA benzyl ester (6-APA-OBn) and Penicillin G (PenG), have been evaluated as catalysts for use in direct cross-aldol reactions in different solvents and mixtures. The effects of catalyst loading, reaction time, pH and temperature on the yield and stereoselectivity have been studied. 6-APA proved to be an effective catalyst in terms of yield

  6-氨基青霉烷酸 (6-APA) 及其两种衍生物 6-APA 苄酯 (6-APA-OBn) 和青霉素 G (PenG) 已被评估为用于不同溶剂中直接交叉羟醛反应的催化剂和混合物。研究了催化剂负载量、反应时间、pH 值和温度对产率和立体选择性的影响。就环己酮和对硝基苯甲醛之间的反应收率而言，6-APA 被证明是一种有效的催化剂，尤其是在纯条件下。反应的立体选择性受两种竞争机制的影响：一种是亚胺-烯胺途径，另一种是布朗斯台德酸催化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)