4-hydroxy-4-(naphthalen-4-yl)-butan-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-hydroxy-4-(naphthalen-4-yl)-butan-2-one
• 英文别名: 4-hydroxy-4-(naphthalen-1-yl)butan-2-one；4-hydroxy-4-naphthalen-1-ylbutan-2-one
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: ZRQWPFKGJLGSPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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-(naphthalen-4-yl)-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 100.0h， 以34%的产率得到(4R)-4-hydroxy-4-(1'-naphthyl)-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-萘甲醛 、 丙酮 在 三氟甲磺酸 作用下， 反应 96.17h， 以91%的产率得到4-hydroxy-4-(naphthalen-4-yl)-butan-2-one
  参考文献：
  名称：

  磁性纳米粒子的不对称双功能伯氨基催化。

  摘要：

  开发了MNP负载的手性伯胺催化剂，并在直接的醛醇缩合反应中将其评估为不对称双官能烯胺催化剂，在11次循环后显示出基本不变的活性和立体选择性。

  DOI：

  10.1039/b812958d

文献信息

• 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。
• Functionalized ionic liquids catalyzed direct aldol reactions
  作者：Sanzhong Luo、Xueling Mi、Long Zhang、Song Liu、Hui Xu、Jin-Pei Cheng

  DOI：10.1016/j.tet.2006.12.079

  日期：2007.2

  A series of functionalized ionic liquids (FILs) incorporated with chiral-pyrrolidine unit have been synthesized and tested as reusable organocatalysts for direct aldol reactions. FIL 1b in combination with acetic acid and water as additives could effectively catalyze direct aldol reactions of various ketone donors in high yields and the FIL catalyst was easily recycled and reused for six times with

  已合成了一系列与手性吡咯烷单元结合的功能化离子液体（FIL），并已测试它们可作为可直接用于羟醛直接反应的有机催化剂。FIL 1b与乙酸和水作为添加剂的组合可以有效地高产率催化各种酮供体的直接羟醛反应，并且FIL催化剂易于回收利用，可重复使用六次，但活性略有降低。基于实验观察和以前的报道，我们提出反应是通过顺烯胺中间体发生的，并且FIL中的离子液体部分为参与的醛受体提供了一定的空间屏蔽，这说明了在反应中观察到的适度的对映选择性。
• A Highly Efficient Organocatalyst for Direct Aldol Reactions of Ketones with Aldedydes
  作者：Zhuo Tang、Zhi-Hua Yang、Xiao-Hua Chen、Lin-Feng Cun、Ai-Qiao Mi、Yao-Zhong Jiang、Liu-Zhu Gong

  DOI：10.1021/ja0510156

  日期：2005.6.1

  prepared and evaluated for catalyzing the direct Aldol reaction of 4-nitrobenzaldehyde with acetone. Catalysts with strong electron-withdrawing groups are found to exhibit higher catalytic activity and enantioselectivity than their analogues with electron-donating groups. The presence of 2 mol % catalyst 4g significantly catalyzes the direct Aldol reactions of a wide range of aldehydes with acetone

  制备了衍生自各种手性 β-氨基醇的 L-脯氨酸酰胺，这些醇在其立体中心具有各种电子性质的取代基，并评估其催化 4-硝基苯甲醛与丙酮的直接羟醛反应。发现具有强吸电子基团的催化剂比具有给电子基团的类似物表现出更高的催化活性和对映选择性。2 mol % 催化剂 4g 的存在显着催化了范围广泛的醛与丙酮和丁酮的直接羟醛反应，得到具有非常高的对映选择性的 β-羟基酮，范围从 96% 到 >99% ee。对于来自环己酮反应的抗羟醛产物观察到 95/5 的高非对映选择性，
• Zr(OtBu)4-catalysed synthesis of acetone aldol adducts and domino aldol-Tishchenko reactions with diacetone alcohol as enol equivalent
  作者：Christoph Schneider、Markus Hansch

  DOI：10.1039/b102941j

  日期：——

  Zr(OtBu)4 was found to be a potent catalyst for the synthesis of acetone aldol adducts with diacetone alcohol as enol equivalent and for domino aldol-Tishchenko reaction giving rise to 1,3-anti-diol monoesters with excellent diastereoselectivity.

  Zr(OtBu)4 被发现是一种有效的催化剂，可用于以双丙酮醇为烯醇等价物合成丙酮醛醇加合物，并用于多米诺醛醇-Tishchenko 反应生成具有优异非对映选择性的 1,3-抗二醇单酯。
• Fluorogenic aldehydes bearing arylethynyl groups: turn-on aldol reaction sensors for evaluation of organocatalysis in DMSO
  作者：Nobuyuki Mase、Taishi Ando、Fumiya Shibagaki、Atsushi Sugita、Tetsuo Narumi、Mitsuo Toda、Naoharu Watanabe、Fujie Tanaka

  DOI：10.1016/j.tetlet.2014.02.007

  日期：2014.3

  Fluorogenic aromatic aldehydes bearing arylethynyl groups were developed. They were used for monitoring the reaction progress of organocatalytic aldol reactions in DMSO through an increase in the fluorescence intensity based on the formation of the florescent aldol product. The ratios of the fluorescence intensities of the aldols to the aldehydes were more than 300. These results suggest that the fluorescence assay system using the aldehyde is useful for the rapid identification of superior aldol catalysts and reaction conditions. (c) 2014 Elsevier Ltd. All rights reserved.