2-[(4-fluorophenyl)(hydroxy)methyl]cyclopentan-one | 1364122-01-9

• 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-[(4-fluorophenyl)(hydroxy)methyl]cyclopentan-one
• 英文别名: 2-[(4-Fluorophenyl)-hydroxymethyl]cyclopentan-1-one；2-[(4-fluorophenyl)-hydroxymethyl]cyclopentan-1-one
• CAS: 1364122-01-9
• 化学式: C₁₂H₁₃FO₂
• 分子量: 208.232
• InChiKey: RRMNLTZFRCOUDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氟苯甲醛 、 环戊酮 在 methyl 12-(D-prolinoylamino)cholate 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 生成 2-[(4-fluorophenyl)(hydroxy)methyl]cyclopentan-one 、 2-[(4-fluorophenyl)(hydroxy)methyl]cyclopentan-one
  参考文献：
  名称：

  Methyl 12-[d-prolinoylamino]cholate as a versatile organocatalyst for the asymmetric aldol reaction of cyclic ketones

  摘要：

  The use of cholic acid derivative 1, bearing a D-prolinamide moiety linked at the 12-position of cholic acid methylester, as an organocatalyst in the asymmetric aldol reaction of cyclic ketones and aromatic aldehydes, gave the corresponding aldol products in good yield and ee up to 98%. This organocatalyst has proven to be efficient both in water and in organic solvent, where it has been used with a 1% loading. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.023

文献信息

• 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。
• Highly efficient primary amine organocatalysts for the direct asymmetric aldol reaction in brine
  作者：Xiao Ma、Chao-Shan Da、Lei Yi、Ya-Ning Jia、Qi-Peng Guo、Li-Ping Che、Feng-Chun Wu、Jun-Rui Wang、Wei-Ping Li

  DOI：10.1016/j.tetasy.2009.05.032

  日期：2009.7

  amine organocatalysts, derived from natural primary amino acids, in combination with 2,4-dinitrophenol (DNP) have proven to be efficient in the presence of brine without further addition of organic solvents. The system formed by 1f and DNP was the most efficient one; it can catalyze the direct aldol reaction with a broad range of ketones and aromatic aldehydes, giving the corresponding aldol products

  由六种衍生自天然伯氨基酸的伯胺有机催化剂与2,4-二硝基苯酚（DNP）组合而成的有机催化系统已证明在盐水存在下无需进一步添加有机溶剂即可有效。由1f和DNP组成的系统是最有效的系统。它可以与广泛的酮和芳族醛催化直接的羟醛反应，以高收率提供相应的羟醛产物，具有高达近乎完美的非对映体和对映体选择性（最高99/1顺/反，对映体> 99％ee）。
• (<scp>l</scp>)-Prolinamide imidazolium hexafluorophosphate ionic liquid as an efficient reusable organocatalyst for direct asymmetric aldol reaction in solvent-free condition
  作者：Geeta Devi Yadav、Surendra Singh

  DOI：10.1039/c6ra23652a

  日期：——

  We have designed a new hydrophobic ionic liquid derived from bromoester of trans-4-hydroxy-(L)-prolinamide and N-methylimidazole. (L)-Prolinamide imidazolium hexafluorophosphate ionic liquid (2 mol%) found to be an excellent organocatalyst for direct...

  我们设计了一种新的疏水性离子液体，该液体衍生自反式-4-羟基-（L）-脯氨酰胺和N-甲基咪唑的溴酸酯。（L）-脯氨酰胺六氟磷酸咪唑鎓离子液体（2 mol％）被发现是直接...
• Direct Asymmetric Aldol Reactions in Water Catalysed by a Highly Active <i>C</i> ₂ ‐Symmetrical Bisprolinamide Organocatalyst
  作者：Joshua P. Delaney、Luke C. Henderson

  DOI：10.1002/adsc.201100667

  日期：2012.1

  A novel C2‐symmetrical bisprolinamide organocatalyst was synthesised and used to facilitate asymmetric direct aldol reactions in a water emulsion. Reactions were performed at room temperature with very low catalyst loadings (1–2.5 mol%) without the required use of additives, co‐catalysts or extended reaction times (24 h). This catalyst system was then used with a variety of aldehyde substrates showing

  合成了一种新型的C 2-对称双脯氨酰胺有机催化剂，并用于促进水乳液中的不对称直接羟醛反应。反应是在室温下以极低的催化剂负载量（1-2.5％摩尔）进行的，无需使用添加剂，助催化剂或延长反应时间（24小时）。然后，该催化剂体系与各种醛底物一起使用，显示出对苯甲醛与环己酮的良好反应通用性（dr范围为77/23至> 99/1，抗/ syn；ee范围为33％至> 99％）和中等范围的环戊酮（dr范围45/55至76/24，反/同步；ee范围从14％到68％）。还研究了超低催化剂负载量（0.1和0.05 mol％），表明催化剂的周转量约为1000。
• Synergistic effects within a C2-symmetric organocatalyst: the potential formation of a chiral catalytic pocket
  作者：Joshua P. Delaney、Hannah L. Brozinski、Luke C. Henderson

  DOI：10.1039/c3ob27250h

  日期：——

  This study describes the synthesis of five novel C2-symmetric organocatalysts that facilitate the on-water asymmetric aldol reaction at low catalyst loading (1 mol%) without the use of additives. Each catalyst is composed of two diprolinamide units joined by a symmetric alkyl bridging group allowing for systematic modulation of catalytic site proximity. Typically, catalysts in this manuscript which bear the catalytic units in close proximity gave the best reaction outcomes in terms of conversion (up to >99%), diastereomeric ratio (4/96, syn/anti) and enantiomeric excess (up to 97%). This effect has been attributed to the assembly of a chiral pocket, facilitated by hydrogen bonding at the oil-in-water interface.

  本研究介绍了五种新型 C2 对称有机催化剂的合成，这些催化剂可在不使用添加剂的情况下，以较低的催化剂负载量（1 摩尔%）促进水上不对称醛醇反应。每种催化剂都由两个二烯丙基酰胺单元组成，并由一个对称的烷基桥基连接，从而可以系统地调节催化位点的邻近性。通常情况下，本手稿中催化位点距离较近的催化剂在转化率（高达 >99%）、非对映异构体比率（4/96，同/反）和对映异构体过量（高达 97%）方面的反应效果最好。这种效果归因于在水包油界面的氢键作用下形成的手性口袋。