4-hydroxy-4-(2-naphthyl)butan-2-one | 229156-79-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-hydroxy-4-(2-naphthyl)butan-2-one
• 英文别名: 4-hydroxy-4-(naphthalen-2-yl)butan-2-one；4-Hydroxy-4-naphthalen-2-ylbutan-2-one；4-hydroxy-4-naphthalen-2-ylbutan-2-one
• CAS: 229156-79-0
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: MXVTULUUAPPLRM-UHFFFAOYSA-N

物化性质

• 沸点：
  391.5±22.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  4-hydroxy-4-(2-naphthyl)butan-2-one 在 NH₂-Val-(D-Pro)-Gly-Leu-OH 、 苯甲酸 作用下， 以 乙醇 为溶剂， 反应 90.0h， 以29%的产率得到(R)-4-Hydroxy-4-naphthalen-2-yl-butan-2-one
  参考文献：
  名称：

  Highly enantioselective biomimetic intramolecular dehydration: kinetic resolution of β-hydroxy ketones catalyzed by β-turn tetrapeptides

  摘要：

  Racemic beta-hydroxy ketones were kinetically resoluted into the enantiopure isomers and (E)-alpha,beta-unsaturated ketones using catalytic asymmetric intramolecular dehydration for the first time. Synthetic tetrapeptides were used to imitate fatty acid dehydratases to efficiently discriminate racemic beta-hydroxy ketones, enantioselectively catalyze the intramolecular dehydration, and result in highly enantioenriched beta-hydroxy and (E)-alpha,beta-unsaturated ketones in the environmentally benign process. Mechanistically, the high discrimination of the racemic substrates and successive enantioselective dehydration are highly dependent on the cooperative catalysis of the NH2 and COOH groups of the peptide. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.087
• 作为产物：
  描述：

  1-萘-2-基丁烷-1,3-二酮 在 sodium tetrahydroborate 、 bovine serum albumin 作用下， 以 水 、 乙腈 为溶剂， 生成 4-hydroxy-4-(2-naphthyl)butan-2-one 、 3-hydroxy-1-(2-naphthalenyl)-1-butanone
  参考文献：
  名称：

  白蛋白控制的1，3-二酮立体选择性还原为抗二醇。

  摘要：

  高化学选择性和立体选择性的空前组合在白蛋白与芳香族1,3-二酮之间的1：1络合物的NaBH4还原中导致抗1,3-二醇的形成高达96％。

  DOI：

  10.1039/b200474g

文献信息

• Direct aldol and tandem Mannich reactions in room temperature ammonia solutions
  作者：Lichun Feng、Lijin Xu、Kimhung Lam、Zhongyuan Zhou、C.W. Yip、Albert S.C. Chan

  DOI：10.1016/j.tetlet.2005.10.050

  日期：2005.12

  An economical, simple, and efficient direct aldol reaction via the double activation of both aldehydes and ketones by ammonia has been developed. An unprecedented tandem Mannich reaction was observed when hydroxybenzaldehydes, pyrrole-2-carboxyaldehyde, and indole-3-carboxyaldehyde were employed to afford 2,2-dimethyl-6-aryl-4-pyrilidinones in moderate to good yields.

  已经开发了通过氨对醛和酮的双重活化而进行的经济，简单和有效的直接羟醛反应。当使用羟基苯甲醛，吡咯-2-羧基醛和吲哚-3-羧基醛以中等到良好的收率得到2,2-二甲基-6-芳基-4-吡咯烷酮时，观察到了前所未有的串联曼尼希反应。
• Tandem Catalysis by Lipase in a Vinyl Acetate-Mediated Cross-Aldol Reaction
  作者：Manjeet Kumar、Bhahwal A. Shah、Subhash C. Taneja

  DOI：10.1002/adsc.201000980

  日期：2011.5

  The lipase Novozym435 (0.6% w/w) was used in tandem with organocatalysts in a first vinyl/isopropenyl acetate‐mediated aldol reaction. The reaction was facilitated through the lipase‐catalyzed in situ generation of acetaldehyde/acetone. The important features of the present methodology include the mild and facile reaction conditions, regenerability of the lipase, comparatively high yields and minimal

  脂肪酶Novozym435（0.6％w / w）与乙酸乙烯酯/异丙烯基乙酸酯介导的醛醇缩合反应中的有机催化剂一起使用。该反应通过脂肪酶催化的乙醛/丙酮原位生成而得以促进。本方法的重要特征包括温和且容易的反应条件，脂肪酶的可再生性，相对高的收率和最小的副产物形成。
• A Selective Direct Aldol Reaction in Aqueous Media Catalyzed byZinc-Proline
  作者：Ruben Fernandez-Lopez、Jacob Kofoed、Miguel Machuqueiro、Tamis Darbre

  DOI：10.1002/ejoc.200500352

  日期：2005.12

  The Zn–proline complex is shown to catalyze the aldol reaction of acetone and a wide range of arenecarbaldehydes in aqueous media, accepting even deactivated arenecarbaldehydes such as methoxybenzaldehydes in good yields. Enantiomeric excesses of up to 56 % could be obtained with 5 mol-% of the catalyst at room temperature, and up to 66 %

  Zn-脯氨酸配合物可催化丙酮和多种芳烃甲醛在水性介质中的羟醛反应，甚至可以以良好的收率接受失活的芳烃甲醛，例如甲氧基苯甲醛。在室温下使用 5 mol-% 的催化剂可以获得高达 56 % 的对映体过量，高达 66 %
• Chiral Gating for Size- and Shape-Selective Asymmetric Catalysis
  作者：Xiaowei Li、Yan Zhao

  DOI：10.1021/jacs.9b06619

  日期：2019.9.4

  A poor or mediocre stereoselectivity is a key roadblock for a chiral cata-lyst to find practical adoptions. We report a facile method to create a tunable chiral space near a chiral catalyst to augment its selectivity. The space was created rationally through templated polymerization within cross-linked micelles, using readily available amino acid derivatives. It provided gated entrance of reactants

  较差或中等的立体选择性是手性催化剂找到实际应用的主要障碍。我们报告了一种在手性催化剂附近创建可调手性空间以提高其选择性的简便方法。该空间是通过交联胶束内的模板聚合合理创造的，使用容易获得的氨基酸衍生物。它为反应物提供了进入催化剂的门控入口，使普通的脯氨酰胺能够以尺寸和形状选择性的方式以优异的产率和 ee 催化水中的羟醛缩合。
• Chitosan hydrogel: A green and recyclable biopolymer catalyst for aldol and Knoevenagel reactions
  作者：K. Rajender Reddy、K. Rajgopal、C. Uma Maheswari、M. Lakshmi Kantam

  DOI：10.1039/b610355c

  日期：——

  Chitosan hydrogel is efficiently utilized as an organocatalyst for aldol and Knoevenagel reactions, providing the products in high yields with a high chemoselectivity under biphasic conditions. The catalyst was recovered by simple filtration and reused several times without significant loss of activity.

  壳聚糖水凝胶可作为有机催化剂有效地用于醛醇反应和克诺文纳格尔反应，在双相条件下可提供高产率和高化学选择性的产物。通过简单过滤即可回收催化剂，并可多次重复使用而不会明显丧失活性。