(R)-2-(hydroxymethyl)-2-methylcyclohexanone | 252979-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-(hydroxymethyl)-2-methylcyclohexanone
• 英文别名: (R)-2-hydroxymethyl-2-methylcyclohexanone；(2R)-2-(hydroxymethyl)-2-methylcyclohexan-1-one
• CAS: 252979-21-8
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: DZDMVKOFZZKCSM-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  叔丁基二苯基氯硅烷 、 (R)-2-(hydroxymethyl)-2-methylcyclohexanone 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以66%的产率得到(R)-2-(tert-butyldiphenylsiloxymethyl)-2-methylcyclohexanone
  参考文献：
  名称：

  Synthesis of optically active 3-alkoxy-6-hydroxymethyl-6-methyl-2-cyclohexenone

  摘要：

  Optically active 3-alkoxy-6-hydroxymethyl-6-methyl-2-cyclohexenone and 6-acetoxymethyl-3-alkoxy-6-methyl-2-cyclohexenone were efficiently obtained by lipase-catalyzed kinetic resolution. (R)-6-Acetoxymethyl-3-(methoxymethoxy)-6-methyl-2-cyclohexenone was converted to the synthetic intermediate of cassiol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00304-3
• 作为产物：
  描述：

  3-(甲氧基甲氧基)环己-2-烯-1-酮 在 palladium on activated charcoal lipase AK 、 氢气 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 27.5h， 生成 (R)-2-(hydroxymethyl)-2-methylcyclohexanone
  参考文献：
  名称：

  Synthesis of optically active 3-alkoxy-6-hydroxymethyl-6-methyl-2-cyclohexenone

  摘要：

  Optically active 3-alkoxy-6-hydroxymethyl-6-methyl-2-cyclohexenone and 6-acetoxymethyl-3-alkoxy-6-methyl-2-cyclohexenone were efficiently obtained by lipase-catalyzed kinetic resolution. (R)-6-Acetoxymethyl-3-(methoxymethoxy)-6-methyl-2-cyclohexenone was converted to the synthetic intermediate of cassiol. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00304-3

文献信息

• Catalytic Asymmetric Hydroxymethylation of Silicon Enolates Using an Aqueous Solution of Formaldehyde with a Chiral Scandium Complex
  作者：Shunpei Ishikawa、Tomoaki Hamada、Kei Manabe、Shū Kobayashi

  DOI：10.1021/ja047896i

  日期：2004.10.1

  Catalytic asymmetric hydroxymethylation of silicon enolates has been achieved. In this reaction, an aqueous solution of formaldehyde can be used to realize an easy and safe procedure, and high enantioselectivities have been obtained. This is the first example of catalytic asymmetric reactions in aqueous media with a chiral scandium complex.

  已经实现了硅烯醇化物的催化不对称羟甲基化。在该反应中，可以使用甲醛的水溶液来实现简单且安全的过程，并且获得了较高的对映选择性。这是在水性介质中与手性钪络合物进行催化不对称反应的第一个例子。
• Bismuth Triflate−Chiral Bipyridine Complexes as Water-Compatible Chiral Lewis Acids
  作者：Shū Kobayashi、Tsuyoshi Ogino、Haruka Shimizu、Shunpei Ishikawa、Tomoaki Hamada、Kei Manabe

  DOI：10.1021/ol051965w

  日期：2005.10.1

  [reaction: see text] Catalytic asymmetric hydroxymethylation of silicon enolates with an aqueous formaldehyde solution has been developed using a chiral bismuth complex. This is the first example of highly enantioselective reactions using a chiral bismuth catalyst in aqueous media. In this paper, we have added Bi(OTf)(3)-1 complex as a "water-compatible Lewis acid". Bi(OTf)3 is unstable in the presence

  [反应：见正文]使用手性铋配合物已开发出用甲醛水溶液催化的烯醇硅的催化不对称羟甲基化反应。这是在水介质中使用手性铋催化剂进行高对映选择性反应的第一个例子。在本文中，我们添加了Bi（OTf）（3）-1配合物作为“与水相容的路易斯酸”。Bi（OTf）3在水的存在下不稳定，但被碱性配体稳定。
• Lewis Acid Catalysis in Water with a Hydrophilic Substrate: Scandium-Catalyzed Hydroxymethylation with Aqueous Formaldehyde in Water
  作者：Masaya Kokubo、Chikako Ogawa、Shū Kobayashi

  DOI：10.1002/anie.200801849

  日期：2008.8.25
• WO2006/80425
  申请人：——

  公开号：——

  公开（公告）日：——
• Lipase-catalyzed kinetic resolution of α-hydroxymethylcycloalkanones with a quaternary carbon center. Chemoenzymatic synthesis of chiral pseudoiridolactones
  作者：Zineb Guerrab、Stefan Schweiger、Boujemâa Daou、Mohammed Ahmar、Bernard Cazes

  DOI：10.1016/j.tetasy.2010.04.043

  日期：2010.7

  The resolution of alpha-alkyl-alpha-hydroxymethylcyclopentanones 1 and cyclohexanones 3 has been efficiently achieved by using lipase-catalyzed transesterification reactions with vinyl acetate as the acylating agent. The enantiomeric selectivities were dependent on both the ring size of the cycloalkanone and the bulk of the carbon group located at the stereogenic quaternary center. The resolved alpha-alkyl-alpha-hydroxymethylcyclopentanones 1 were used as enantiopure (or enantioenriched) precursors for the synthesis of the optically active pseudoiridolactones 6-7. (C) 2010 Elsevier Ltd. All rights reserved.