(2R,1'R)-2-[hydroxy-(phenyl)methyl]cyclohexanone | 174173-20-7

• 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: (2R,1'R)-2-[hydroxy-(phenyl)methyl]cyclohexanone
• 英文别名: 2-(hydroxyphenylmethyl)cyclohexanone；2-(hydroxy(phenyl)methyl)cyclohexan-1-one；(2R)-2-[(R)-hydroxy(phenyl)methyl]cyclohexan-1-one
• CAS: 174173-20-7
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: YQBZNNFVXOBDSJ-AAEUAGOBSA-N

物化性质

• 沸点：
  355.6±15.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (2R,1'R)-2-[hydroxy-(phenyl)methyl]cyclohexanone 、 氟磺酸甲酯 生成 (2R)-2-[(R)-methoxy(phenyl)methyl]cyclohexan-1-one
  参考文献：
  名称：

  MURATA S.; SUZUKI M.; NOYORI R., J. AMER. CHEM. SOC., 1980, 102, NO 9, 3248-3249

  摘要：

  DOI：
• 作为产物：
  描述：

  环己酮 、 苯甲醛 生成 (2R,1'R)-2-[hydroxy-(phenyl)methyl]cyclohexanone
  参考文献：
  名称：

  J. ORG. CHEM., 53,(1988) N5, C. 5986-5988

  摘要：

  DOI：

文献信息

• Readily Tunable and Bifunctional <scp>l</scp>-Prolinamide Derivatives:  Design and Application in the Direct Enantioselective Aldol Reactions
  作者：Jia-Rong Chen、Hai-Hua Lu、Xin-Yong Li、Lin Cheng、Jian Wan、Wen-Jing Xiao

  DOI：10.1021/ol0520323

  日期：2005.9.1

  [reaction: see text] Readily tunable and bifunctional L-prolinamides as novel organocatalysts have been developed, and their catalytic activities were evaluated in the direct asymmetric Aldol reactions of various aromatic aldehydes and cyclohexanone. High isolated yields (up to 94%), enantioselectivities (up to 99% ee), and anti-diastereoselectivities (up to 99:1) were obtained under the optimal conditions

  [反应：见正文]已开发出易于调节的双功能L-脯氨酰胺作为新型有机催化剂，并在各种芳族醛和环己酮的直接不对称Aldol反应中评估了它们的催化活性。在最佳条件下，获得了高分离产率（高达94％），对映选择性（高达99％ee）和抗非对映选择性（高达99：1）。
• Multifunctional heterocyclic scaffolds for hybrid Lewis acid/Lewis base catalysis of carbon–carbon bond formation
  作者：Dennis Wiedenhoeft、Adam R. Benoit、Yibiao Wu、Jacob D. Porter、Elisia Meyle、Teresa H.W. Yeung、Raechel Huff、Sergey V. Lindeman、Chris Dockendorff

  DOI：10.1016/j.tet.2016.05.014

  日期：2016.7

  classes of hybrid catalysts have been synthesized by tethering heterocyclic metal (Lewis acid) chelating scaffolds to several different amines capable of facilitating enamine catalysis. Oxazole, thiazole, and imidazole-based chiral precatalysts were prepared in several steps from amino acid starting materials, and these were combined with a variety of metal Lewis acids for potential use as catalysts for various

  通过将杂环金属（路易斯酸）螯合支架束缚到能够促进烯胺催化的几种不同的胺上，已经合成了几种新型的杂化催化剂。由氨基酸起始原料分几步制备恶唑，噻唑和咪唑基手性预催化剂，然后将它们与多种金属路易斯酸混合，可潜在地用作形成各种碳-碳键形成的催化剂。鉴定了与活化的苯甲醛受体进行对映选择性直接羟醛反应的耐空气和湿气的催化剂，并结合脯氨酸衍生的恶唑-羧酰胺预催化剂与Zn（OTf）2获得了最佳结果或镧系（III）盐。对照研究支持以下假设，即它们充当丙醛和4-硝基苯甲醛的醛醇缩合反应的单分子杂化催化剂。
• Synthesis of novel silyl enol ethers from chlorodimethyl(naphthylphenylmethyl)silanes having a chiral centre and a ketone and their chirality transfer effects in crossed-aldol reactions
  作者：Kenichi Miyakawa、Takeo Konakahara、Norio Sakai、Kozo Kozawa、Takahiro Gunji、Yukinori Nagao

  DOI：10.3184/030823409x393709

  日期：2009.1

  crystallography was used to determine the stereo structure of a novel chiral organosilicon compound, (2R)-(–)-(1-cyclohexenyloxy)dimethyl(1-naphthylphenylmethyl) silane, which has a chiral centre next to the silicon atom. The crossed-aldol reaction of the silyl enol ether with benzaldehyde gave the corresponding aldol products with high chirality transfer.

  X 射线晶体学用于确定一种新型手性有机硅化合物 (2R)-(-)-(1-环己烯氧基) 二甲基(1-萘基苯基甲基) 硅烷的立体结构，其手性中心靠近硅原子。甲硅烷基烯醇醚与苯甲醛的交叉羟醛反应得到相应的具有高手性转移的羟醛产物。
• Monofunctional primary amine: A new class of organocatalyst for asymmetric Aldol reaction
  作者：KHIANGTE VANLALDINPUIA、PORAG BORA、GHANASHYAM BEZ

  DOI：10.1007/s12039-017-1237-y

  日期：2017.3

  organocatalysts involving a primary amine as the only functional group is developed for catalytic asymmetric aldol reaction of cyclohexanone/cyclopentanone with various aryl aldehydes in the presence of benzoic acid as an additive at −10∘C. In an unexpected observation, the primary amine catalyzed reactions gave excellent yield and good to excellent stereoselectivity, while secondary amines were found to have

  在-10 ° C的条件下，在苯甲酸作为添加剂存在的情况下，开发了一种新型的有机催化剂，其中以伯胺为唯一的官能团，用于环己酮/环戊酮与各种芳基醛的催化不对称醛醇缩合反应。伯胺催化的反应具有出色的收率和良好的立体选择性，而在相似的反应条件下，仲胺的反应性很小或没有。 一类新的与伯胺作为唯一的催化活性官能团aminocatalysts的混合物用于与苯甲酸的存在作为添加剂在-10各种芳基醛的环己酮/环戊酮的不对称催化醛醇缩合反应开发ö整齐的条件下下进行。
• Aqueous Asymmetric Mukaiyama Aldol Reaction Catalyzed by Chiral Gallium Lewis Acid with Trost-Type Semi-Crown Ligands
  作者：Hui-Jing Li、Hong-Yu Tian、Yan-Chao Wu、Yong-Jun Chen、Li Liu、Dong Wang、Chao-Jun Li

  DOI：10.1002/adsc.200505089

  日期：2005.7

  generates highly effective chiral gallium Lewis acid catalysts for aqueous asymmetric aldol reactions of aromatic silyl enol ethers with aldehydes. A ligand-acceleration effect was observed. Water is essential for obtaining high diastereoselectivity and enantioselectivity. The p-phenyl substituent in aromatic silyl enol ether (2 h) plays an important role and increases the enantioselectivity up to 95%

  Ga（OTf）3与手性半冠配体（1a – e）的结合产生了高效的手性镓路易斯酸催化剂，用于芳族甲硅烷基烯醇醚与醛的水性不对称羟醛反应。观察到配体促进作用。水对于获得高非对映选择性和对映选择性是必不可少的。芳基甲硅烷基烯醇醚中的对苯基取代基（2 h）起着重要作用，对映选择性提高至95％ee。尽管脂族甲硅烷基烯醇醚的对映选择性低，而甲硅烷基烯酮缩醛容易在含水醇中水解，但甲硅烷基烯酮硫缩醛的醛醇缩合反应（12）在镓-路易斯酸催化剂的存在下与醛一起以合理的收率和高的非对映异构体（高达99：1）和对映选择性（高达96％ee）提供β-羟基硫酯。