2-hydroxymethylene-(2',6'-dichlorophenyl)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: 2-hydroxymethylene-(2',6'-dichlorophenyl)cyclohexanone
• 英文别名: 2-[hydroxy(2,6-dichlorophenyl)methyl]cyclohexan-1-one；2-[(2,6-dichlorophenyl)-hydroxymethyl]cyclohexan-1-one
• 化学式: C₁₃H₁₄Cl₂O₂
• 分子量: 273.159
• InChiKey: FZYIXDFVZCYBSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 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：
  2

反应信息

• 作为产物：
  描述：

  环己酮 、 2,6-二氯苯甲醛 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 生成 2-hydroxymethylene-(2',6'-dichlorophenyl)cyclohexanone
  参考文献：
  名称：

  The enzymatic asymmetric aldol reaction using acidic protease from Aspergillus usamii

  摘要：

  AUAP (acidic protease from Aspergillus usamii) could catalyze the direct aldol reactions between aromatic aldehydes and cyclic ketones in acetonitrile (MeCN) in the presence of water. The enantioselectivities of up to 88% ee and diastereoselectivities of up to 97:3 (anti/syn) were achieved. This new activity of protease expands the application of the biocatalyst and provides a novel example of enzymatic promiscuity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.056

文献信息

• Primary amine-metal Lewis acid bifunctional catalysts: the application to asymmetric direct aldol reactions
  作者：Zhenghu Xu、Philias Daka、Hong Wang

  DOI：10.1039/b912728c

  日期：——

  The first example of metal Lewis acid-primary amine bifunctional cooperative catalyst derived from primary amino acids was developed, and it was found to catalyze aldol reactions of cyclic ketones highly efficiently with very good to excellent stereoselectivities.

  开发了衍生自伯氨基酸的金属路易斯酸-伯胺双官能协同催化剂的第一个实例，发现它可以非常有效地催化环状酮的醛醇缩合反应，具有非常好的至优异的立体选择性。
• Primary amine-metal Lewis acid bifunctional catalysts based on a simple bidentate ligand: direct asymmetric aldol reaction
  作者：Philias Daka、Zhenghu Xu、Alexandru Alexa、Hong Wang

  DOI：10.1039/c0cc00917b

  日期：——

  A novel class of primary amine-metal Lewis acid bifunctional catalysts based on a bidentate ligand was developed. These catalysts were highly efficient in catalyzing the direct asymmetric aldol reactions of ketones offering excellent stereoselectivity. The aldol reactions required a low catalyst loading (2.5 mol%), and were water compatible.

  开发了一种新型的基于双齿配体的伯胺金属路易斯酸双功能催化剂。这些催化剂在催化具有优异立体选择性的酮类的直接不对称醛醇缩合反应中非常高效。醛醇缩合反应需要低的催化剂负载量（2.5mol％），并且与水相容。
• β-Aminosulfonamide-Catalyzed Direct Asymmetric Aldol Reaction in Brine
  作者：Tsuyoshi Miura、Mariko Ina、Kie Imai、Kosuke Nakashima、Akira Masuda、Norihiro Tada、Nobuyuki Imai、Akichika Itoh

  DOI：10.1055/s-0030-1259317

  日期：2011.2

  Direct asymmetric aldol reactions of aldehydes with ketones inthe presence of a catalytic amount of β-aminosulfonamide 2 and trifluoroacetic acid in brine resultsin the formation of the corresponding ANTI-aldolproducts in high yields with up to 96% enantiomeric excess.The ANTI-aldol products obtained by using organocatalyst 2 have the opposite absolute configurationto those obtained using the similar

  在催化量的 β-氨基磺酰胺 2 和三氟乙酸存在下，醛与酮的直接不对称醛醇反应在盐水中以高产率形成相应的 ANTI-羟醛产物，对映体过量高达 96%。 获得的 ANTI-羟醛产物通过使用有机催化剂 2 与使用类似的磺酰胺催化剂 1 获得的绝对构型相反，这是我们之前报道的。
• Highly efficient asymmetric aldol reaction in brine using a fluorous sulfonamide organocatalyst
  作者：Tsuyoshi Miura、Hikaru Kasuga、Kie Imai、Mariko Ina、Norihiro Tada、Nobuyuki Imai、Akichika Itoh

  DOI：10.1039/c2ob06955e

  日期：——

  A fluorous organocatalyst promotes direct asymmetric aldol reactions of aromatic aldehydes with ketones in brine to afford the corresponding anti-aldol products in high yield with up to 96% ee. Fluorous organocatalyst can be readily recovered by solid phase extraction using fluorous silica gel and reused without purification.

  氟有机催化剂可促进卤水中芳族醛与酮的直接不对称醛醇缩合反应，得到相应的 反醛醇ee高达96％的高产量产品。通过使用氟进行固相萃取，可以很容易地回收含氟有机催化剂硅石 凝胶，无需纯化即可重复使用。
• Aldol Reactions in Water Using a β-Cyclodextrin-Binding Proline Derivative
  作者：Wolf-D. Woggon、Kegang Liu、Daniel Häussinger

  DOI：10.1055/s-2007-985569

  日期：——

  The aldol reaction of various aromatic aldehydes with cyclohexanone is catalyzed by the inclusion complex of a proline derivative and β-cyclodextrin in water, yielding hydroxyketones with anti/syn ratio of up to 99:1 and ee values well above 90%.

  脯氨酸衍生物和 δ² 环糊精的包合物在水中催化了各种芳香醛与环己酮的醛醇反应，生成的羟基酮的反/炔比高达 99:1，ee 值远远超过 90%。