3,4-dihydroxy-4-{4-(trifluoromethyl)phenyl}butan-2-one | 645389-27-1

• 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: 3,4-dihydroxy-4-{4-(trifluoromethyl)phenyl}butan-2-one
• 英文别名: 3,4-Dihydroxy-4-[4-(trifluoromethyl)phenyl]butan-2-one；3,4-dihydroxy-4-[4-(trifluoromethyl)phenyl]butan-2-one
• CAS: 645389-27-1
• 化学式: C₁₁H₁₁F₃O₃
• 分子量: 248.202
• InChiKey: HLFCYIVYTAYUAF-UHFFFAOYSA-N

物化性质

• 沸点：
  361.7±37.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 羟基丙酮 在 antibody aldolase 38C₂ 、 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 作用下， 反应 336.0h， 以89%的产率得到3,4-dihydroxy-4-{4-(trifluoromethyl)phenyl}butan-2-one
  参考文献：
  名称：

  Synthesis of fluorinated materials catalyzed by proline or antibody 38C2 in ionic liquid

  摘要：

  The utility of reusable ionic liquid-proline (or aldolase antibody 38C2) reaction system, proceeding the aldol reactions, is described. Further. obtained alpha-chloro-beta-hydroxy compounds were transformed to the optically active alpha,beta-epoxy carbonyl compounds. The aldolase antibody 3SC2-ionic liquid system was able to reuse in Michael additions and the reaction of fluoromethylated imines. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(03)00032-0

文献信息

• Pepsin-catalyzed direct asymmetric aldol reactions for the synthesis of vicinal diol compounds
  作者：Ling-Yu Li、Da-Cheng Yang、Zhi Guan、Yan-Hong He

  DOI：10.1016/j.tet.2015.01.061

  日期：2015.3

  The catalytic promiscuity of pepsin from porcine gastric mucous was observed in catalysis of the direct asymmetric aldol reactions of aromatic aldehydes with acetones, which were substituted by hydroxy-, dihydroxy-, methoxy- and benzyloxy- for the synthesis of diol compounds in acetonitrile. This biocatalysis was also applicable to the aldol reactions of cyclic or hetereocyclic ketones with aromatic

  在催化芳香族醛与丙酮直接不对称醛醇缩合反应的催化过程中，观察到了胃蛋白酶对胃蛋白酶的混杂作用，丙酮醛被羟基，二羟基，甲氧基和苄氧基所取代，从而在乙腈中合成二醇化合物。该生物催化也适用于环状或杂环酮与芳族醛的醛醇缩合反应。获得了高达87％的产率，高达> 99/1 dr的非对映选择性和高达75％ee的对映选择性。
• Chiral 1,2-diaminocyclohexane as organocatalyst for enantioselective aldol reaction
  作者：Yi Liu、Junfeng Wang、Qi Sun、Runtao Li

  DOI：10.1016/j.tetlet.2011.04.116

  日期：2011.7

  catalyze the asymmetric aldol reaction in MeOH–H2O. Cyclic ketones as aldol substrates gave the anti-β-hydroxyketone products with moderate to good yields, diastereoselectivity and enantioselectivity (up to 78% yield, >20:1 anti/syn, 94% ee). Hydroxyacetone as aldol substrate afforded the syn-α, β-dihydroxyketones as major products in up to 85% yield with good enantioselectivity (up to >20:1 syn/anti

  一个简单的和可商购的手性1,2-二氨基环己烷作为催化剂，己二酸作为助催化剂能有效地催化在MeOH-H不对称醛醇缩合反应2 O.环酮类如醇醛底物，得到反-β-羟基酮产品具有中度至良好的收率，非对映选择性和对映选择性（高达78％的收率，抗/顺式> 20：1，94％ee）。羟丙酮作为醇醛底物以主要产物顺-α，β-二羟基酮的形式提供了高达85％的收率和良好的对映选择性（高达> 20：1 syn / anti，93％ee）。
• Organocatalyzed Highly Enantioselective Direct Aldol Reactions of Aldehydes with Hydroxyacetone and Fluoroacetone in Aqueous Media: The Use of Water To Control Regioselectivity
  作者：Xiao-Hua Chen、Shi-Wei Luo、Zhuo Tang、Lin-Feng Cun、Ai-Qiao Mi、Yao-Zhong Jiang、Liu-Zhu Gong

  DOI：10.1002/chem.200600801

  日期：2007.1.2

  exhibited high regio- and enantioselectivities for the direct aldol reactions of hydroxyacetone and fluoroacetone with aldehydes in aqueous media. It was found that water could be used to control the regioselectivity. The presence of 20-30 mol% of the catalyst afforded the direct aldol reactions of a wide range of aldehydes with hydroxyacetone to give the otherwise disfavored products with excellent

  由（2R，3R）-2-氨基-3-羟基琥珀酸二乙基二乙酯和L-脯氨酸制得的有机催化剂对羟基丙酮和氟丙酮与醛在水性介质中的直接羟醛反应具有很高的区域选择性和对映选择性。发现水可以用于控制区域选择性。20-30mol％的催化剂的存在提供了广泛的醛与羟基丙酮的直接羟醛反应，得到了否则不利的产物，其具有优良的对映选择性，从91至99％ee，和高的区域选择性。在水性介质中，氟丙酮与醛的醛化反应由30 mol％的有机催化剂介导，优先发生在甲基上，产生具有高对映选择性（最高91％ee）的产物；然而，这些添加主要发生在THF中的氟甲基上。光学活性的3，5-二取代的四氢呋喃和（2S，4R）-二羟基-4-联苯丁酸是从羟丙酮的醛醇缩合反应开始制备的。关于水在控制区域选择性中的作用的理论研究表明，脯氨酸酰胺的酰胺氧，羟基丙酮的羟基与水之间形成的氢键是通过以明确的一个水分子作为氢键供体进行微溶剂化而实现区域选择性的原因。和/或接受者。
• Additive-controlled regioselective direct asymmetric aldol reaction of hydroxyacetone and aldehyde
  作者：Ling-yan Liu、Bing Wang、Yunna Zhu、Wei-xing Chang、Jing Li

  DOI：10.1016/j.tetasy.2013.03.018

  日期：2013.5

  developed for the direct asymmetric aldol reaction of hydroxyacetone and various aldehydes with moderate to high yields and high enantioselectivities. More importantly, this regioselective reaction could be easily regulated by changing the additives in the presence of the same organocatalyst 1b, to afford the normal 1,2-diol adducts and the disfavoured 1,4-diol products, respectively, in a highly regioselective

  已经开发了由1-脯氨酸和1-缬氨酸制备的结构简单的二肽衍生物1b，用于羟丙酮和各种醛的直接不对称醛醇缩合反应，具有中等至高收率和高对映选择性。更重要的是，可以通过在相同的有机催化剂1b的存在下改变添加剂来轻松地调节区域选择性反应，从而以高度区域选择性的方式分别提供正构1,2-二醇加合物和不利的1,4-二醇产物。还提出了可能的反应机理。
• Chiral amine organocatalysts for the syn-aldol reaction involving substituted benzaldehydes and hydroxyacetone
  作者：Dhruba Sarkar、Kurt Harman、Subrata Ghosh、Allan D. Headley

  DOI：10.1016/j.tetasy.2011.05.021

  日期：2011.5

  A new series of cyclohexanediamine organocatalysts that contain the primary amine functionality has been designed, synthesized and tested as catalysts for the asymmetric aldol reaction involving hydroxyacetone and a variety of substituted benzaldehydes. High enantioselectivites and diasteroselectivites were obtained using catalyst la for these reactions. A key step in this reaction for the formation of the syn-product is the formation of a stable intramolecular hydrogen bonded Z-enamine isomer, which in addition to the steric bulk of the catalyst, serve to dictate the course of the stereochemical outcome of the reaction. (C) 2011 Elsevier Ltd. All rights reserved.