2-[hydroxy(4-methoxyphenyl)methyl]cyclohexanone | 160084-47-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[hydroxy(4-methoxyphenyl)methyl]cyclohexanone
• 英文别名: 2-(hydroxy(4-methoxyphenyl)methyl)cyclohexan-1-one；2-[hydroxy-(4-methoxyphenyl)methyl]cyclohexan-1-one
• CAS: 160084-47-9
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: PMOKMSPZEONZGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[hydroxy(4-methoxyphenyl)methyl]cyclohexanone 在 草酸 作用下， 生成 E-2-(4-methoxybenzylidene)cyclohexanone
  参考文献：
  名称：

  可的松的简单类似物。第四部分 一些苄基取代的乙醇酰基环己醇

  摘要：

  DOI：

  10.1039/jr9550001126
• 作为产物：
  描述：

  1-环己烯氧基三甲基硅烷 、 4-甲氧基苯甲醛 在 ytterbium(III) triflate 作用下， 以 水 为溶剂， 反应 20.0h， 以77%的产率得到2-[hydroxy(4-methoxyphenyl)methyl]cyclohexanone
  参考文献：
  名称：

  水性介质中甲硅烷基烯醇醚与醛的醛醇缩合反应

  摘要：

  通过使用镧系三氟甲烷磺酸盐作为催化剂，在水性介质中成功地进行了甲硅烷基烯醇醚与醛的醛醇缩合反应。水溶性醛是适用的，并且该催化剂可以回收并在该反应中重复使用。

  DOI：

  10.1016/s0040-4039(00)91691-5

文献信息

• Dibutyltin dimethoxide-catalyzed aldol reaction of enol trichloroacetates
  作者：Akira Yanagisawa、Takayuki Sekiguchi

  DOI：10.1016/s0040-4039(03)01840-9

  日期：2003.9

  A catalytic aldol condensation of aldehydes with enol trichloroacetates was achieved using dibutyltin dimethoxide as a novel catalyst in a mixed solvent consisting of THF and MeOH. Various β-hydroxy ketones were diastereoselectively obtained in high yields up to 99%.

  使用二甲基二丁基锡作为新型催化剂，在由THF和MeOH组成的混合溶剂中，实现醛与烯醇三氯乙酸酯的醛醇缩合催化缩合反应。以高达99％的高收率非对映选择性地获得了各种β-羟基酮。
• Reactive barium-promoted Reformatsky-type reaction of α-chloroketones with aldehydes
  作者：Akira Yanagisawa、Hiroshi Takahashi、Takayoshi Arai

  DOI：10.1039/b314752p

  日期：——

  A Reformatsky-type aldol reaction of α-chloroketones with aldehydes has been achieved using reactive barium as a low-valent metal in THF; this one-pot process is more effective for obtaining the desired β-hydroxy ketones in high yields than the stepwise process in which barium enolates are prepared prior to the reaction with aldehydes.

  使用活性钡作为低价金属，在THF中实现了α-氯代酮与醛的Reformatsky型羟醛反应；这种一步法过程比先制备钡烯醇盐再与醛反应的分步过程更有效地以高产率获得所需的β-羟基酮。
• 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。
• Synthesis and Characterization of Monosaccharide Derivatives and Application of Sugar-Based Prolinamides in Asymmetric Synthesis
  作者：Jyoti Agarwal、Rama Krishna Peddinti

  DOI：10.1002/ejoc.201200522

  日期：2012.11

  were converted into the corresponding prolinamide organocatalysts (i.e., 1a, 2a, 3a, and 3b) in high yields. The catalytic activity of these sugar-based prolinamide organocatalysts was demonstrated in asymmetric aldol reactions in various solvents and at different temperatures. The oraganocatalyst 3a was shown to be an efficient and powerful organocatalyst for the enantioselective aldol reaction of various

  首次合成、分离和使用N-乙酰氨基葡萄糖衍生物甲基2-乙酰氨基-3,4,6-三-O-苄基-2-脱氧-β-D-吡喃葡萄糖苷(9b)的β-异头体用于合成糖基伯胺4b。糖基伯胺 5a、一对单糖衍生物 6a 和 6b 以及所有这些化合物的前体也被合成、分离并通过标准光谱方法进行了充分研究，包括 1H-1H COZY 和 HSQC 等 2D NMR 光谱实验. 然后将糖基伯胺 4a、5a、6a 和 6b 以高产率转化为相应的脯氨酰胺有机催化剂（即 1a、2a、3a 和 3b）。这些糖基脯氨酰胺有机催化剂的催化活性在各种溶剂和不同温度下的不对称羟醛反应中得到证明。
• Towards peptide isostere libraries: aqueous aldol reactions on hydrophilic solid supports
  作者：Anette Graven、Morten Grøtli、Morten Meldal

  DOI：10.1039/a909246c

  日期：——

  Polar polyoxyethylene-polyoxypropylene (POEPOP) resin was derivatised with a 4-hydroxymethyl phenoxy linker and used as a solid support for lanthanide triflate catalysed Mukaiyama type solid phase aldol reactions. The conditions were optimised using resin bound 4-alkoxybenzaldehyde and it was shown that use of an aqueous solvent was crucial. Also, the reactions were performed with an N-terminal peptide aldehyde substrate in very high yields. POEPOP resins prepared with different monomer chain lengths and commercially available PEG-grafted NovaSyn TG resin were compared in the reactions.

  聚氧乙烯-聚氧丙烯（POEPOP）树脂通过含有4-羟甲基苯氧基的连接剂进行衍生化，并作为固体载体用于镧系三氟甲磺酸盐催化的Mukaiyama型固相羟醛反应。通过树脂结合的4-烷氧基苯甲醛优化反应条件，并证明使用水溶剂是关键。此外，反应在N端肽醛底物上进行了极高的产率。比较了具有不同单体链长度的POEPOP树脂和市售PEG接枝的NovaSyn TG树脂在反应中的性能。