ethyl 3-hydroxy-2,2-dimethyl-5-phenylpentanoate | 133270-74-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl 3-hydroxy-2,2-dimethyl-5-phenylpentanoate
• CAS: 133270-74-3；133270-75-4；134924-29-1
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: AZJMWEUDMRDZOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  366.9±30.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  ethyl 3-hydroxy-2,2-dimethyl-5-phenylpentanoate 在 甲醇 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 2.0h， 以80%的产率得到3-hydroxy-2,2-dimethyl-5-phenylpentanoic acid
  参考文献：
  名称：

  MNBA-Mediated β-Lactone Formation: Mechanistic Studies and Application for the Asymmetric Total Synthesis of Tetrahydrolipstatin

  摘要：

  Various beta-lactones were prepared from beta-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.

  DOI：

  10.1021/jo300139r
• 作为产物：
  描述：

  异丁酸乙酯 在 盐酸 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.08h， 生成 ethyl 3-hydroxy-2,2-dimethyl-5-phenylpentanoate
  参考文献：
  名称：

  Metal Chloride-Promoted Aldol Reaction of α-Dimethylsilylesters with Aldehydes, Ketones, and α-Enones

  摘要：

  在氯化锂（LiCl）的催化量存在下，α-二甲基硅醚（α-DMS-酯）1在30°C下顺利与各种醛反应，以良好至高收率生成醇醛化合物。另一方面，酮的醇醛反应更有效地被氯化镁（MgCl2）而非氯化锂（LiCl）促进。α-烯酮也能在羰基碳或β-碳上经历金属氯化物促进的1的加成反应。

  DOI：

  10.1055/s-2005-871938

文献信息

• 1,4-Bis(trimethylsilyl)-1,4-diaza-2,5-cyclohexadienes as Strong Salt-Free Reductants for Generating Low-Valent Early Transition Metals with Electron-Donating Ligands
  作者：Teruhiko Saito、Haruka Nishiyama、Hiromasa Tanahashi、Kento Kawakita、Hayato Tsurugi、Kazushi Mashima

  DOI：10.1021/ja501313s

  日期：2014.4.2

  reduction of Cp2TiCl2, for which compounds 2a and 4 gave the corresponding one-electron reduced products, pyrazine-bridged and 4,4'-bipyridyl-bridged dimeric Ti(III) complexes 5 and 6, and compounds 2b and 2c afforded the same double chloride-bridged dimeric Ti(III) complex, [Cp2Ti]2(μ-Cl)2 (7), though 1a and 1b could not reduce Cp2TiCl2. Application of the organosilicon compounds as reducing agents for catalytic

  富电子有机硅化合物，例如 1,4-双(三甲基甲硅烷基)-1,4-二氮杂-2,5-环己二烯 (2a)、2,5-二甲基-1,4-双(三甲基甲硅烷基)-1,4 -二氮杂-2,5-环己二烯(2b)、2,3,5,6-四甲基-1,4-双(三甲基甲硅烷基)-1,4-二氮杂-2,5-环己二烯(2c)和1,1 '-bis(trimethylsilyl)-1,1'-dihydro-4,4'-bipyridine (4), 作为 4-6 族金属氯化物络合物的通用还原剂，如 Cp2TiCl2、Cp*2TiCl2 (Cp* = η (5)-C5Me5)、Cp*TiCl3、Cp*TaCl4 和 WCl4(PMe2Ph)2，以无盐方式生成相应的低价金属物种。含氮还原剂，如 2a-c 和 4，比母体有机硅还原剂 3,6-双(三甲基甲硅烷基)-1,4-环己二烯 (1a) 和 1-甲基-3,6-双具有更强的还原能力(三甲基甲硅烷基)-1
• Activation of ketene silyl acetals by 10-methylacridinium perchlorate: a novel catalysis in mukaiyama reaction
  作者：Junzo Otera、Yoshiyuki Wakahara、Hidenobu Kamei、Tsuneo Sato、Hitosi Nozaki、Shinichi Fukuzumi

  DOI：10.1016/s0040-4039(00)79935-7

  日期：1991.5

  10-Methylacridinium perchlorate (1) effectively promotes various reactions of ketene silyl acetals: aldol and Michael addition products are obtained with aldehydes, ketones, acetals, and α-enones. The reactions exhibit unusual dependency upon 1, namely the yields are excellent when a catalytic amount of 1 is employed whereas no desired products are accessible by the use of 1 in a stoichiometric quantity

  10-甲基ac啶高氯酸盐（1）有效地促进乙烯酮甲硅烷基乙缩醛的各种反应：醛，酮，乙缩醛和α-烯酮可得到醛醇和迈克尔加成产物。反应表现出对1的不寻常依赖性，即当使用催化量1时，收率优异，而通过使用化学计量的1不能获得所需产物。提出了一种新颖的催化循环。
• Scope and mechanism of the electrochemical Reformatsky reaction of α-haloesters on a graphite powder cathode in aqueous anolyte
  作者：Carlos A. de Souza、Marcelo Navarro、Lothar W. Bieber、Madalena C.C. Areias

  DOI：10.1016/j.electacta.2014.03.118

  日期：2014.6

  carbonyl compounds were submitted to electrochemical coupling on a graphite powder cathode using aqueous anolyte free of organic solvents. Preparative yields of coupling products could be obtained with ethyl 2-bromoisobutyrate and aromatic aldehydes. Ethyl 2-bromopropionate was much less efficient. Extensive variation of applied potential, electrolyte composition, stoichiometry, catalyst, leaving halogen

  使用不含有机溶剂的水性阳极电解液，将六种α-卤代酸酯和十八种羰基化合物在石墨粉末阴极上进行电化学偶联。用2-溴异丁酸乙酯和芳族醛可以制得偶合产物。2-溴丙酸乙酯的效率低得多。施加的电势，电解质组成，化学计量，催化剂，在羰基化合物上留下卤素和活化取代基的广泛变化导致了这样的结论，即在大多数情况下，反应机理是通过卤化物还原产生的自由基中间体进行的。氯乙酸乙酯仅产生痕量的偶联产物，最可能是通过碳负离子机理产生的。
• The catalytic asymmetric aldol reaction of silyl ketene acetals with aldehydes in the presence of a chiral borane complex. Nitroethane as a highly effective solvent for catalytic conditions
  作者：Syun-ichi Kiyooka、Yuichi Kaneko、Ken-ichi Kume

  DOI：10.1016/s0040-4039(00)61236-4

  日期：1992.8

  Catalytic asymmetric aldol reactions of silyl ketene acetals with aldehydes in the presence of 20 mol % of the chiral borane reagent, prepared in situ from the p-nitrobenzenesulfonamide of (S)-valine and BH3·THF complex, gave β-hydroxy carboxylic acid esters in good chemical yields along with excellent enantioselectivity under conditions that employ nitroethane as an effective solvent.

  由（S）-缬氨酸的对硝基苯磺酰胺和BH 3 ·THF配合物原位制备的手性硼烷试剂在20摩尔％的存在下，硅酮烯酮缩醛与醛的催化不对称醛醇缩醛反应，得到β-羟基羧酸在使用硝基乙烷作为有效溶剂的条件下，该酯具有良好的化学收率以及出色的对映选择性。
• Enantioselective Aldol Reaction Using Bornane-2,3-diol-Aluminum Complex as a Chiral Lewis Acid
  作者：Makoto Shimizu、Manabu Kawamoto、Yasushi Yamamoto、Tamotsu Fujisawa

  DOI：10.1055/s-1997-6148

  日期：1997.6

  β-Hydroxy ester was formed in high enantiomeric excess by the reaction of ketene silyl acetal with aldehyde in the presence of a chiral Lewis acid prepared from diethylaluminum chloride and chiral diol derived from (+)-camphor.

  在由二乙基氯化铝和从右旋樟脑衍生出的手性二醇制备的手性路易斯酸存在下，烯酮硅乙缩醛与醛反应，生成高对映体过量的β-羟基酯。