(R)‐2‐((S)-hydroxy(pyridin‐3-yl)methyl)cyclohexan-1‐one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (R)‐2‐((S)-hydroxy(pyridin‐3-yl)methyl)cyclohexan-1‐one
• 英文别名: (R)-2-((S)-hydroxy(pyridin-3-yl)methyl)cyclohexanone；(S)-2-((R)-hydroxy(pyridin-3-yl)methyl)cyclohexanone；2-(hydroxy(pyridin-3-yl)methyl)cyclohexanone；(2R)-2-[(S)-hydroxy(pyridin-3-yl)methyl]cyclohexan-1-one
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: XVYDXWWNDNPDBN-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-吡啶甲醛 、 环己酮 在 C₁₀H₁₄N₂*CHF₃O₂S 作用下， 反应 36.0h， 以92%的产率得到(R)‐2‐((S)-hydroxy(pyridin‐3-yl)methyl)cyclohexan-1‐one
  参考文献：
  名称：

  新型氨基 Tf-酰胺有机催化剂的设计：不对称醛醇合成的环境友好方法

  摘要：

  8-氨基-1-四氢萘酮可以很容易地制备出一种新型的光学纯伯氨基芳香Tf-酰胺有机催化剂，并在不对称醛醇和曼尼希反应的背景下研究了其化学行为。最值得注意的是，不对称羟醛反应在盐水中顺利进行。

  DOI：

  10.1055/s-0037-1610408

文献信息

• Chiral 1,2-diaminocyclohexane as organocatalyst for enantioselective aldol reaction
  作者：Yi Liu、Junfeng Wang、Qi Sun、Runtao Li

  DOI：10.1016/j.tetlet.2011.04.116

  日期：2011.7

  catalyze the asymmetric aldol reaction in MeOH–H2O. Cyclic ketones as aldol substrates gave the anti-β-hydroxyketone products with moderate to good yields, diastereoselectivity and enantioselectivity (up to 78% yield, >20:1 anti/syn, 94% ee). Hydroxyacetone as aldol substrate afforded the syn-α, β-dihydroxyketones as major products in up to 85% yield with good enantioselectivity (up to >20:1 syn/anti

  一个简单的和可商购的手性1,2-二氨基环己烷作为催化剂，己二酸作为助催化剂能有效地催化在MeOH-H不对称醛醇缩合反应2 O.环酮类如醇醛底物，得到反-β-羟基酮产品具有中度至良好的收率，非对映选择性和对映选择性（高达78％的收率，抗/顺式> 20：1，94％ee）。羟丙酮作为醇醛底物以主要产物顺-α，β-二羟基酮的形式提供了高达85％的收率和良好的对映选择性（高达> 20：1 syn / anti，93％ee）。
• Ionic liquid as a recyclable and efficient medium for lipase-catalyzed asymmetric cross aldol reaction
  作者：Yang Zhang、Na Wang、Zong-Bo Xie、Long-Hua Zhou、Xiao-Qi Yu

  DOI：10.1016/j.molcatb.2014.10.008

  日期：2014.12

  from porcine pancreas) was found to catalyze asymmetric cross aldol reactions of aromatic and heteroaromatic aldehydes with various ketones in ionic liquid ([BMIM][PF6]) for the first time. Interestingly, PPL exhibited high catalytic activity and excellent stereoselectivity in this efficient and recyclable room temperature ionic liquid in the presence of moderate water, similar to the results obtained

  在离子液体（[BMIM] [PF 6 ]）中，首次发现PPL（猪胰腺脂肪酶）催化芳香族和杂芳香族醛与各种酮的不对称交叉羟醛反应。有趣的是，在中等水存在下，PPL在这种高效且可回收的室温离子液体中表现出高催化活性和出色的立体选择性，类似于在有机溶剂中获得的结果。获得了高达99％的高收率，高达90％ee的优异对映选择性以及高达> 99：1 dr的良好非对映选择性。
• Enantioselective synthesis of β-hydroxy ketones from heterocyclic aldehydes in water catalyzed by a recyclable organocatalyst bearing an ionic liquid moiety
  作者：D. E. Siyutkin、A. S. Kucherenko、S. G. Zlotin

  DOI：10.1007/s11172-009-0258-1

  日期：2009.9

  The aldol reactions of cyclic (heterocyclic) ketones and heterocyclic aldehydes catalyzed by (4R,S)-4-hydroxyproline modified with a ionic liquid moiety proceed with high yields and diastereo- and enantioselectivity in the presence of water. The catalyst retained its activity and selectivity for at least five cycles.

  由离子液体部分改性的 (4R,S)-4-羟基脯氨酸催化的环（杂环）酮和杂环醛的羟醛反应在水存在下以高产率和非对映选择性和对映选择性进行。催化剂在至少五个循环内保持其活性和选择性。
• Biocatalytic asymmetric aldol reaction in buffer solution
  作者：Zong-Bo Xie、Na Wang、Guo-Fang Jiang、Xiao-Qi Yu

  DOI：10.1016/j.tetlet.2012.12.022

  日期：2013.2

  A green and convenient protocol has been developed for asymmetric cross-aldol reaction. In this Letter, bovine pancreatic lipase (BPL) was first reported to catalyze the aldol reaction and acidic buffer was first used for promiscuous enzymatic aldol reaction. (C) 2012 Elsevier Ltd. All rights reserved.
• Water promoted enantioselective aldol Reaction by proline-cholesterol and -diosgenin based amphiphilic organocatalysts
  作者：Ting He、Kun Li、Ming-Yu Wu、Ming-Bo Wu、Na Wang、Lin Pu、Xiao-Qi Yu

  DOI：10.1016/j.tet.2013.04.078

  日期：2013.6

  A series of proline-cholesterol and -diosgenin based amphiphilic organocatalysts were developed for the first time, and their catalytic activities for the enantioselective aldol reaction were investigated. The results indicated that water can significantly enhance the activity and stereoselectivity of the transformation via micelle formation. TEM and AFM analysis demonstrated that the diameter of the micelle particles ranged from 200 to 800 nm. (C) 2013 Elsevier Ltd. All rights reserved.