2-(hydroxy-cyclohexyl-methyl)-cyclohexanone | 1332625-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(hydroxy-cyclohexyl-methyl)-cyclohexanone
• 英文别名: (R)-2-[(R)-cyclohexyl(hydroxyl)methyl]cyclohexanone；(R)-2-((R)-cyclohexyl(hydroxy)methyl)cyclohexanone；(2R)-2-[(R)-cyclohexyl(hydroxy)methyl]cyclohexan-1-one
• CAS: 1332625-64-5
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: JENOANYCOLGWMY-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 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 、 环己烷基甲醛 在 2,4-二硝基酚 、 (S)-N-((S)-1-oxo-1-((4-(piperidin-1-yl)pyridin-2-yl)amino)-propan-2-yl)pyrrolidine-2-carboxamide 、 sodium chloride 作用下， 以 水 为溶剂， 反应 40.0h， 以32%的产率得到2-(hydroxy-cyclohexyl-methyl)-cyclohexanone
  参考文献：
  名称：

  Proline-based dipeptides as efficient organocatalysts for asymmetric aldol reactions in brine

  摘要：

  Simple N-proline-based dipeptides with two N-H groups in combination with 2,4-dinitrophenol (DNP) catalyze the direct asymmetric aldol reactions of aldehydes with a broad range of ketones to furnish the corresponding aldol products in high yields (up to 99%) and with high enantioselectivities (up to 97%) and diastereoselectivities (up to > 99:1, anti/syn) at room temperature and in brine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.017

文献信息

• Highly Enantioselective Co-Catalytic Direct Aldol Reactions by Combination of Hydrogen-Bond Donating and Acyclic Amino Acid Catalysts
  作者：Guangning Ma、Agnieszka Bartoszewicz、Ismail Ibrahem、Armando Córdova

  DOI：10.1002/adsc.201100408

  日期：2011.11

  Highly enantioselective co-catalytic direct aldol reactions by a combination of simple hydrophobic acyclic amino acid and hydrogen-bond donating catalysts are presented. The corresponding aldol products are formed in high yields with high regio-, diastereo- (anti or syn) and enantioselectivity (up to 99.5:0.5 er). The catalyst loadings can be decreased to as little as 2 mol%.

  提出了通过简单的疏水性无环氨基酸和氢键给体催化剂的组合的高度对映选择性的共催化直接羟醛反应。相应的醛醇产物以高收率，高区域选择性，非对映异构性（反式或顺式）和对映选择性（高达99.5：0.5 er）形成。催化剂的负载量可降低至低至2 mol％。
• L-Proline/CoCl2-Catalyzed Highly Diastereo- and Enantioselective Direct Aldol Reactions
  作者：Ananta Karmakar、Tapan Maji、Sebastian Wittmann、Oliver Reiser

  DOI：10.1002/chem.201101299

  日期：2011.9.19

  AbstractThe CoCl2/L‐proline (1:2) system was found to be an excellent catalyst for direct aldol reactions. Excellent yields (up to 93 %) and a significant improvement in diastereoselectivity (anti/syn up to 45:1) as well as enantioselectivity (up to more than 99 % ee) compared with using proline as the sole catalyst were observed. This catalyst system was successfully applied to both cyclic and acyclic ketones in combination with aromatic and aliphatic aldehydes. In situ chelation of CoCl2 and proline (1:2) is proposed to promote the reaction through a six‐membered Zimmermann–Traxler type transition state involving the positioning of proline‐enamine and the aldehyde through chelation to CoII.