(2S)-2-[(R)-hydroxy(naphthalen-2-yl)methyl]cyclopentan-1-one | 1118764-42-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S)-2-[(R)-hydroxy(naphthalen-2-yl)methyl]cyclopentan-1-one
• CAS: 1118764-42-3
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: DAGNKZSTMNRBRU-ZBFHGGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  2-环戊烯酮 、 2-萘甲醛 在 二苯甲基硅烷 、 Rh(Phebox-Ph)(OAc)2(H₂O) 、 盐酸 、 水 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 、 (2S)-2-[(R)-hydroxy(naphthalen-2-yl)methyl]cyclopentan-1-one
  参考文献：
  名称：

  Intermolecular Antiselective and Enantioselective Reductive Coupling of Enones and Aromatic Aldehydes with Chiral Rh(Phebox) Catalysts

  摘要：

  The intermolecular reductive coupling reaction of cyclopent-2-enone and aromatic aldehydes was realized by chiral rhodium-(bisoxazolinyl)phenyl catalysts, Rh(Phebox-Ph)(OAc)(2)(H2O), with diphenymethylsilane as a hydride donor to give the corresponding beta-hydroxyketones in high anti selectivity (up to 96%) with high enantioselectivity (up to 93%).

  DOI：

  10.1021/ol802939u

文献信息

• New Simple Hydrophobic Proline Derivatives as Highly Active and Stereoselective Catalysts for the Direct Asymmetric Aldol Reaction in Aqueous Medium
  作者：Francesco Giacalone、Michelangelo Gruttadauria、Paolo Lo Meo、Serena Riela、Renato Noto

  DOI：10.1002/adsc.200800555

  日期：——

  different hydrophobic properties of the acyl group were easily synthesized and used as catalysts in the direct asymmetric aldol reaction between cyclic ketones (cyclohexanone and cyclopentanone) and several substituted benzaldehydes. Reactions were carried out using water, this being the best reaction medium examined. Screening of these catalysts showed that compounds bearing the most hydrophobic acyl

  容易合成具有不同疏水性的酰基的新的4-取代的酰氧基脯氨酸衍生物，并将其用作环酮（环己酮和环戊酮）与几种取代的苯甲醛之间的直接不对称羟醛反应的催化剂。使用水进行反应，这是所检验的最佳反应介质。对这些催化剂的筛选表明，带有最多疏水性酰基链的化合物[4-苯基丁酸酯和4-（吡啶-1-基）丁酸酯]提供了更好的结果。后一种催化剂在室温下仅以2摩尔％的比例成功使用，无需添加添加剂，即可获得具有出色立体选择性的羟醛产物。这些结果表明脯氨酸部分在4-位上带有适当的简单疏水取代基的衍生化可以提供高活性和立体选择性的催化剂，而无需在分子中另外的手性主链。最后，提供了在水存在下观察到的立体选择性的解释。
• New simple and recyclable O-acylation serine derivatives as highly enantioselective catalysts for the large-scale asymmetric direct aldol reactions in the presence of water
  作者：Chuanlong Wu、Xiangkai Fu、Shi Li

  DOI：10.1016/j.tet.2011.03.083

  日期：2011.6

  products in high yields (up to 99%) and enantioselectivities (up to 99% ee). The catalyst 1b can be easily recovered and reused, and without significant decrease of enantioselectivity was observed for five cycles. This novel catalyst can be efficiently used in large-scale reactions with the enantioselectivities being maintained at the same level, which offers a great possibility for application in industry

  通过在室温下在三氟乙酸中将丝氨酸与酰氯合理结合，一步合成了新型的O-酰化丝氨酸衍生的有机催化剂。任何步骤均不涉及保护基团或色谱技术，某些组合的丝氨酸表面活性剂有机催化剂可介导酮与一系列芳香醛的直接羟醛反应，从而以高收率（高达99％）和对映选择性提供羟醛产物。 （最高99％ee）。催化剂1b可以容易地回收和再利用，并且在五个循环中未观察到对映选择性的显着降低。这种新催化剂可以有效地用于大规模反应，同时将对映选择性保持在同一水平，这为工业应用提供了很大的可能性。
• Biomimetic asymmetric aldol reactions catalyzed by proline derivatives attached to β-cyclodextrin in water
  作者：Hai-Min Shen、Hong-Bing Ji

  DOI：10.1016/j.tetlet.2012.04.140

  日期：2012.7

  Two proline derivatives, (S)-2-aminomethylpyrrolidine and (R)-2-aminomethylpyrrolidine modified beta-CD (CD-1, CD-2) were synthesized in the yields of 31% and 14%. Their self-inclusion conformations were characterized by H-1 ROESY NMR studies and quantum calculation. When CD-1 was applied to asymmetric aldol reactions, up to 94% ee was obtained. Substrate selectivity was also observed in these asymmetric aldol reactions. (C) 2012 Elsevier Ltd. All rights reserved.
• Intermolecular Antiselective and Enantioselective Reductive Coupling of Enones and Aromatic Aldehydes with Chiral Rh(Phebox) Catalysts
  作者：Takushi Shiomi、Takahiro Adachi、Jun-ichi Ito、Hisao Nishiyama

  DOI：10.1021/ol802939u

  日期：2009.2.19

  The intermolecular reductive coupling reaction of cyclopent-2-enone and aromatic aldehydes was realized by chiral rhodium-(bisoxazolinyl)phenyl catalysts, Rh(Phebox-Ph)(OAc)(2)(H2O), with diphenymethylsilane as a hydride donor to give the corresponding beta-hydroxyketones in high anti selectivity (up to 96%) with high enantioselectivity (up to 93%).