3-羟基-3-苯基丁酸乙酯 | 2293-60-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3-羟基-3-苯基丁酸乙酯
• 英文名称: ethyl 3-hydroxy-3-phenylbutyrate
• 英文别名: ethyl 3-hydroxy-3-phenylbutanoate；3-Hydroxy-3-phenyl-buttersaeure-aethylester
• CAS: 2293-60-9
• 化学式: C₁₂H₁₆O₃
• mdl: MFCD00554351
• 分子量: 208.257
• InChiKey: RBHSZNSXPDPHSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-羟基-3-苯基丁酸乙酯 在 diisopropyl aluminum hydride 、 对甲苯磺酸 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 12.0h， 生成 3-phenylbut-2-en-1-ol
  参考文献：
  名称：

  Murphy, John A.; Patterson, Christopher W., Journal of the Chemical Society. Perkin transactions I, 1993, # 4, p. 405 - 410

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-二甲基苯甲酰胺 在 六甲基磷酰三胺 、 仲丁基锂 、 samarium(III) trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 3.0h， 生成 3-羟基-3-苯基丁酸乙酯
  参考文献：
  名称：

  Samarium(II) Triflate as a New Reagent for the Grignard-Type Carbonyl Addition Reaction

  摘要：

  On treatment of a THF solution of Sm(OTf)(3) with 1 equiv of an organolithium or organomagnesium reagent-at ambient temperature, the purple or deep green solution of the divalent samarium triflate [Sm(OTf)(2)] was readily obtained. For this preparation, s-BuLi was the most effective as was evidenced by the reduction of a-phenylethyl iodide in the presence of HMPA. The Sm(OTf)(2) reagent mediated the Grignard-type reaction effectively in THF/HMPA; alkylation and allylation of ketones or aldehydes with alkyl, allyl, or benzyl halides proceeded via organosamarium intermediates. Diastereoselectivity of the samarium-Grignard reaction was examined using 2-methylcyclohexanone, 4-tert-butylcyclohexanone, and 2-phenylpropanal and was found to be higher in each case than that with SmI2. With 2-methylcyclohexanone, for example, Sm(OTf)(2) gave the greatest ratio of axial alcohol:equatorial alcohol = 99:1, and SmI2 gave a ratio of 91:9. Halides containing an ester or a silyl group were reactive in the Reformatsky- or Peterson-type reaction, respectively, using the Sm(OTf)(2) reagent.

  DOI：

  10.1021/jo960260s

文献信息

• Dihydropyrrolones as bacterial quorum sensing inhibitors
  作者：Basmah Almohaywi、Tsz Tin Yu、George Iskander、Daniel S.H. Chan、Kitty K.K. Ho、Scott Rice、David StC. Black、Renate Griffith、Naresh Kumar

  DOI：10.1016/j.bmcl.2019.03.004

  日期：2019.5

  through quorum sensing (QS), which is an intercellular communication system mediated by the binding of signaling molecules to QS receptors such as LasR. In this study, a range of dihydropyrrolone (DHP) analogues were synthesized via the lactone-lactam conversion of lactone intermediates. The synthesized compounds were tested for their ability to inhibit QS, biofilm formation and bacterial growth of

  细菌通过群体感应（QS）调节其致病性和生物膜形成，群体感应是一种细胞间通讯系统，通过信号分子与QS受体（例如LasR）的结合而介导。在这项研究中，通过内酯中间体的内酯-内酰胺转化合成了一系列二氢吡咯烷酮（DHP）类似物。测试了合成的化合物抑制铜绿假单胞菌的QS，生物膜形成和细菌生长的能力。这些化合物也停靠在LasR晶体结构中，以合理化所观察到的结构-活性关系。在这项研究中鉴定出的最具活性的化合物是化合物9i，在31.25 µM时QS抑制率为63.1％，在250 µM时生物膜减少了60％，对细菌细胞的生长只有中等毒性。
• Iron(0)-Mediated Reformatsky Reaction for the Synthesis of β-Hydroxyl Carbonyl Compounds
  作者：Xuan-Yu Liu、Xiang-Rui Li、Chen Zhang、Xue-Qiang Chu、Weidong Rao、Teck-Peng Loh、Zhi-Liang Shen

  DOI：10.1021/acs.orglett.9b01999

  日期：2019.8.2

  An efficient, economical, and practical Reformatsky reaction of α-halo carbonyl compounds with aldehydes/ketones by using cheap and commercial iron(0) powder as reaction mediator is developed. The reactions proceeded effectively in the presence of a catalytic amount of iodine (20 mol %) to afford the synthetically useful β-hydroxyl carbonyl compounds in moderate to good yields.

  通过使用廉价的市售铁（0）粉末作为反应介质，开发了α-卤代羰基化合物与醛/酮的高效，经济和实用的Reformatsky反应。该反应在催化量的碘（20mol％）的存在下有效地进行，以中等至良好的产率提供了合成上有用的β-羟基羰基化合物。
• Tungsten and molybdenum 2-oxaallyl [.eta.1-(C)-enolate] complexes: functional group transformations, photochemical aldol reactions, and alkyne/carbon monoxide migratory insertion reactions
  作者：Elizabeth R. Burkhardt、Jeffrey J. Doney、Robert G. Bergman、Clayton H. Heathcock

  DOI：10.1021/ja00241a020

  日期：1987.4

  Preparation des complexes oxa-2alkyl (η 1 -enolate) par reaction de C 5 R 5 (CO) 3 M − Ne + avec les α-chloroesters, les cetones et les amides. Structures cristallines de certains complexes

  C 5 R 5 (CO) 3 M - Ne + avec les α-氯酯、les cetones 和 les 酰胺的合成 oxa-2 烷基 (η 1 -烯醇化物) par 反应的制备。某些复合体的晶体结构
• Cp2ZrCl2-induced Reformatsky and Barbier reactions on isatins: an efficient synthesis of 3-substituted-3-hydroxyindolin-2-ones
  作者：Mangilal Chouhan、Ratnesh Sharma、Vipin A. Nair

  DOI：10.1002/aoc.1789

  日期：2011.6

  rapid one‐pot process for Reformatsky and Barbier reactions using a catalytic quantity of zirconocene dichloride (Cp2ZrCl2) as a promoter and zinc as a terminal reductant at room temperature in dimethyl formamide was developed. The protocol has wide substrate suitability and afforded the desired 3‐substituted‐3‐hydroxyindolin‐2‐ones from istains in good yields and short reaction time. Copyright © 2011

  开发了一种温和快速的一锅法，用于Reformatsky和Barbier反应，该方法使用催化量的二氯化锆（Cp 2 ZrCl 2）作为促进剂，锌在室温下的二甲基甲酰胺中作为末端还原剂。该方案具有广泛的底物适用性，并从玉米中获得了所需的3-取代-3-羟基吲哚-2-酮，收率高且反应时间短。版权所有©2011 John Wiley＆Sons，Ltd.
• Access to β-Hydroxyl Esters via Copper-Catalyzed Reformatsky Reaction of Ketones and Aldehydes
  作者：Ren Shi Luo、Lu Ouyang、Jian Hua Liao、Yan Ping Xia

  DOI：10.1055/s-0040-1707110

  日期：2020.9

  An efficient and simple Cu-catalyzed Reformatsky reaction of ketones and aldehydes has been accomplished with ethyl iodoacetate. Excellent yields of β-hydroxyl esters were achieved with a range of ketones and aldehydes, which varied from aromatic to aliphatic, unsaturated to saturated ketones and aldehydes. This practical and convenient transformation was conducted with inexpensive, readily available

  用碘乙酸乙酯完成了一种有效且简单的铜催化的酮和醛的 Reformatsky 反应。使用一系列酮和醛（从芳香族到脂肪族、从不饱和到饱和的酮和醛）可实现出色的 β-羟基酯收率。这种实用且方便的转化是在温和的反应条件下使用廉价、容易获得和商业化的原料进行的。