2-(hydroxy(2,4-dichlorophenyl)methyl)cyclohexan-1-one | 852108-97-5

• 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-(hydroxy(2,4-dichlorophenyl)methyl)cyclohexan-1-one
• 英文别名: 2-[(2,4-dichlorophenyl)-hydroxymethyl]cyclohexan-1-one
• CAS: 852108-97-5
• 化学式: C₁₃H₁₄Cl₂O₂
• 分子量: 273.159
• InChiKey: AZKWDMAFEDZXCB-UHFFFAOYSA-N

物化性质

• 沸点：
  413.4±30.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  2-(hydroxy(2,4-dichlorophenyl)methyl)cyclohexan-1-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 环己酮,2-[(2,4-二氯苯基)亚甲基]-
  参考文献：
  名称：

  The Synthesis and Fungicidal Activity of 2-Substituted 1-Azol-1-ylmethyl-6-arylidenecyclohexanols

  摘要：

  DOI：

  10.1002/(sici)1096-9063(199702)49:2<125::aid-ps506>3.0.co;2-0
• 作为产物：
  描述：

  环己酮 、 2,4-二氯苯甲醛 在 水 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 potassium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.05h， 以79%的产率得到2-(hydroxy(2,4-dichlorophenyl)methyl)cyclohexan-1-one
  参考文献：
  名称：

  一种高效的 RuIII/BINAP 催化体系，用于酮与各种醛的醛醇反应

  摘要：

  使用 Ru III /(S)-BINAP 系统在室温下合成了具有中等至优异立体选择性的醛醇加合物。在超声波照射下，羟醛产物在相当短的时间内产生。

  DOI：

  10.3998/ark.5550190.0011.914

文献信息

• SULFONAMIDE-BASED ORGANOCATALYSTS AND METHOD FOR THEIR USE
  申请人：Carter Rich Garrett

  公开号：US20100184986A1

  公开（公告）日：2010-07-22

  Organocatalysts, particularly proline sulfonamide organocatalysts, having a first general formula as follows are disclosed. Embodiments of a method for using these organocatalysts also are disclosed. The method comprises providing a disclosed organocatalyst, and performing a reaction, often an enantioselective or diastereoselective reaction, using the organocatalyst. Solely by way of example, disclosed catalysts can be used to perform aldol reactions, conjugate additions, Michael additions, Robinson annulations, Mannich reactions, α-aminooxylations, α-hydroxyaminations, α-aminations and alkylation reactions. Certain of such reactions are intramolecular cyclizations used to form cyclic compounds, such as 5- or 6-membered rings, having one or more chiral centers. Disclosed organocatalysts generally are much more soluble in typical solvents used for organic synthesis than are known compounds. Moreover, the reaction yield is generally quite good with disclosed compounds, as is their enantioselective and diastereoselective effectiveness.

  披露了具有如下一般公式之一的有机催化剂，尤其是脯氨酸磺酰胺有机催化剂。还披露了使用这些有机催化剂的方法的实施例。该方法包括提供一种披露的有机催化剂，并使用该有机催化剂进行反应，通常是立体选择性的反应或对映选择性反应。仅作为示例，披露的催化剂可用于进行aldol反应、共轭加成、Michael加成、Robinson环化反应、Mannich反应、α-氨基氧化、α-羟基胺化、α-胺化和烷基化反应。其中一些反应是分子内环化反应，用于形成具有一个或多个手性中心的环状化合物，例如5或6元环。披露的有机催化剂通常比已知的化合物更容易溶于用于有机合成的典型溶剂中。此外，使用披露化合物的反应收率通常相当好，它们的对映选择性和非对映选择性效果也很好。
• The Influence of Acidity on Direct Aldol Reactions Catalyzed by Pyrrolidine/Acid Bifunctional Organocatalyst
  作者：Yungui Peng、Changyun Ji、Chengzhi Huang、Ning Wang、Yaozhong Jiang

  DOI：10.1055/s-2005-864823

  日期：——

  match of the acidity and basicity is very important to obtain good reactivity and high yield in the pyrrolidine/acid bifunctional organocatalyst system. The combination of pyrrolidine/p-nitrophenol was a high efficiency catalyst, which has been employed in the direct aldol reaction of aldehydes and ketones with yields up to 99%.

  酸碱度的匹配对于在吡咯烷/酸双功能有机催化剂体系中获得良好的反应性和高产率非常重要。吡咯烷/对硝基苯酚的组合是一种高效催化剂，已用于醛和酮的直接羟醛反应，收率高达99%。
• Highly efficient prolinamide-based organocatalysts for the direct asymmetric aldol reaction in brine
  作者：Ya-Ning Jia、Feng-Chun Wu、Xiao Ma、Gong-Jian Zhu、Chao-Shan Da

  DOI：10.1016/j.tetlet.2009.04.013

  日期：2009.6

  Four prolinamide-based organocatalysts were readily synthesized and applied to the direct asymmetric aldol reactions of ketones and aromatic aldehydes in brine. When 2,4-dinitrophenol (DNP) was used as an acidic additive, 1 mol % low loading of 2b afforded aldol products with excellent diastereoselectivity of up to 98/2 dr and high enantioselectivity of up to 97% ee.

  易于合成四种基于脯氨酰胺的有机催化剂，并将其用于在盐水中酮和芳族醛的直接不对称羟醛反应。当使用2,4-二硝基苯酚（DNP）作为酸性添加剂时，1 mol％的2b低负载量可提供羟醛产物，其非对映选择性高达98/2 dr，对映选择性高达97％ee。
• Asymmetric aldol reaction organocatalyzed by bifunctional N-prolyl sulfinamides under solvent-free conditions
  作者：Wen Wan、Wei Gao、Guobin Ma、Lei Ma、Fan Wang、Jing Wang、Haizhen Jiang、Shizheng Zhu、Jian Hao

  DOI：10.1039/c4ra03362k

  日期：——

  A class of chiral bifunctional N-prolyl sulfinamide and its TFA salts were prepared and proven to be effective for catalyzing the aldol reaction under solvent-free conditions. In general, the corresponding aldol adducts were obtained with high to excellent yields, and satisfactory diastereo-selectivities and enantioselectivities. A matching effect between chiral proline and sulfinamide moieties was

  制备了一类手性双官能N-脯氨酰基亚磺酰胺及其TFA盐，并证明其在无溶剂条件下可有效催化羟醛反应。通常，以高至优异的产率以及令人满意的非对映选择性和对映选择性获得了相应的羟醛加合物。在催化剂中观察到手性脯氨酸和亚磺酰胺部分之​​间的匹配效果。发现在不对称的羟醛合成中两种对映体的对映转换均由脯氨酰基部分主导。
• Nuclease p1: a new biocatalyst for direct asymmetric aldol reaction under solvent-free conditions
  作者：Hai-Hong Li、Yan-Hong He、Yi Yuan、Zhi Guan

  DOI：10.1039/c0gc00486c

  日期：——

  The unnatural ability of nuclease p1 from Penicillium citrinum was first discovered to catalyze asymmetric aldol reactions between aromatic aldehydes and cyclic ketones under solvent-free conditions. The excellent enantioselectivities of up to 99% ee and high diastereoselectivities of up to >99 : 1 (anti/syn) were achieved. This nuclease p1 catalyzed reaction provided a novel case for new activities of existing enzymes, which widens the applicability of this biocatalyst in organic synthesis.

  首次发现了柠檬青霉的核酸酶 p1 在无溶剂条件下催化芳香醛和环酮之间不对称醛醇反应的非天然能力。其对映选择性高达 99% ee，非对映选择性高达 >99 ：1（反/合成）。该核酸酶 p1 催化反应为现有酶的新活性提供了一个新的案例，从而拓宽了这种生物催化剂在有机合成中的应用范围。