2-[(2-chlorophenyl)hydroxymethyl]cyclopentanone | 1068139-77-4

• 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-[(2-chlorophenyl)hydroxymethyl]cyclopentanone
• 英文别名: (R)-2-((R)-(2-chlorophenyl)(hydroxy)methyl)cyclopentan-1-one；2-[hydroxy-(2-chlorophenyl)-methyl]-cyclopentan-1-one；2-(hydroxy(2-chlorophenyl)methyl)cyclopentanone；(2R)-2-[(R)-(2-Chlorophenyl)hydroxymethyl]cyclopentanone；(2R)-2-[(R)-(2-chlorophenyl)-hydroxymethyl]cyclopentan-1-one
• CAS: 1068139-77-4
• 化学式: C₁₂H₁₃ClO₂
• 分子量: 224.687
• InChiKey: WXNTWFXFEZTSCK-CABZTGNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  2

反应信息

• 作为产物：
  描述：

  2-氯苯甲醛 、 环戊酮 在 2,4-二硝基酚 、 C₁₃H₁₈N₄O₂ 、 sodium chloride 作用下， 以 水 为溶剂， 反应 12.0h， 生成 2-[(2-chlorophenyl)hydroxymethyl]cyclopentanone 、 2-(hydroxy-(2-chlorophenyl)-methyl)-cyclopentanone
  参考文献：
  名称：

  Proline-based dipeptides as efficient organocatalysts for asymmetric aldol reactions in brine

  摘要：

  Simple N-proline-based dipeptides with two N-H groups in combination with 2,4-dinitrophenol (DNP) catalyze the direct asymmetric aldol reactions of aldehydes with a broad range of ketones to furnish the corresponding aldol products in high yields (up to 99%) and with high enantioselectivities (up to 97%) and diastereoselectivities (up to > 99:1, anti/syn) at room temperature and in brine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.017

文献信息

• 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。
• 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。
• <i>N</i>-(<i>p</i>-Dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: A Practical Proline Mimetic for Facilitating Enantioselective Aldol Reactions
  作者：Hua Yang、Rich G. Carter

  DOI：10.1021/ol801941j

  日期：2008.10.16

  A highly practical and readily available proline surrogate has been developed with improved solubility properties in common, nonpolar organic solvents. This sulfonamide-based catalyst has proven highly effective at facilitating enantioselective and diastereoselective aldol reactions with a range of substrates in nonpolar organic solvents in the presence of a single equivalent of water. Additionally

  一种高度实用且易于获得的脯氨酸替代品已被开发出来，其在常见非极性有机溶剂中的溶解度得到改善。事实证明，这种磺酰胺基催化剂在单当量水存在下，在非极性有机溶剂中能够非常有效地促进与一系列底物的对映选择性和非对映选择性羟醛反应。此外，在不存在任何有机溶剂的情况下，可以使用低至 2 mol% 的催化剂负载，并具有持续的高水平选择性。
• Highly Stereoselective and Scalable <i>anti</i>-Aldol Reactions Using <i>N</i>-(<i>p</i>-Dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: Scope and Origins of Stereoselectivities
  作者：Hua Yang、Subham Mahapatra、Paul Ha-Yeon Cheong、Rich G. Carter

  DOI：10.1021/jo1015008

  日期：2010.11.5

  A highly enantio- and diastereoselective anti-aldol process (up to >99% ee, >99:1 dr) catalyzed by a proline mimetic—N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide—has been developed. Catalyst loading as low as 2 mol % can be employed. Use of industry-friendly solvents for this transformation as well as neat reaction conditions have been demonstrated. The scope of this transformation on a range

  一种由脯氨酸模拟物N- (对十二烷基苯磺酰基)-2-吡咯烷甲酰胺催化的高度对映和非对映选择性反羟醛过程（高达 >99% ee，>99:1 dr）已被开发出来。可以使用低至2mol%的催化剂负载。已经证明可以使用工业友好型溶剂进行这种转化以及纯净的反应条件。探索了这种对一系列醛和酮的转化范围。密度泛函理论计算表明，增强的非对映选择性的起源是由于磺酰胺、亲电子试剂和催化剂烯胺之间存在非经典氢键，有利于 Houk−List 模型中主要的反 Re 醛醇TS 。
• Both Amide-Bearing α- and β-Amino Acids from Natural Aspartic Acid Are Efficient Organocatalysts for Enantioselective Aldol Reactions
  作者：Gen-Fa Wen、Rui Zhang、Chao-Shan Da、Chu-Yu Zhang

  DOI：10.1055/a-1953-1656

  日期：2023.2

  of structurally similar α- and β-amino acids in an asymmetric aldol transformation. Interestingly, aspartic acid is not only an α-amino acid, but also a β-amino acid. Thus, by modifying one of the two acidic groups of aspartic acid, two sets of α- and β-amino acids, 14 amino acids in total, were prepared and used as organocatalysts. The two types of amino acid, interestingly, achieved similar high catalytic

  这项工作旨在比较和探索结构相似的α-和β-氨基酸在不对称醛醇转化中的不同催化效率。有趣的是，天冬氨酸不仅是一种α-氨基酸，也是一种β-氨基酸。因此，通过修饰天冬氨酸的两个酸性基团之一，制备了两组α-和β-氨基酸，总共14个氨基酸，并用作有机催化剂。有趣的是，这两种氨基酸在不同的最佳条件下在不对称醛醇转化中实现了相似的高催化效率。在某些情况下，理想的 β-氨基酸甚至比理想的 α-氨基酸实现了显着更高的对映选择性，尽管 α-氨基酸在这种不对称转化中被广泛证明是高效的有机催化剂。