3-羟基-3-(2-甲基苯基)丙酸乙酯 | 70200-17-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-羟基-3-(2-甲基苯基)丙酸乙酯
• 英文名称: (-)-3-hydroxy-3-(2-methylphenyl)propionic acid ethyl ester
• 英文别名: Ethyl 3-Hydroxy-3-(o-tolyl)propanoate；ethyl 3-hydroxy-3-(2-methylphenyl)propanoate
• CAS: 70200-17-8
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: ROEXEQUWIZEEDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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-(2-甲基苯基)丙酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium hydride 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 32.08h， 生成 ethyl 2-(2-methylbenzoyl)-5-phenylpent-4-ynoate
  参考文献：
  名称：

  CAN促进的Pd（PPh 3）2 Cl 2催化氧化环化反应中速率的提高：2-酮呋喃-4-羧酸酯的合成

  摘要：

  化学计量的硝酸铈铵（CAN）和Pd（PPH催化量3）2氯2（5摩尔％）可以迅速产生通过氧化多取代2- ketofuran -4-羧酸酯由2-丙炔-1,3-酮酯ø -环化反应。发现Pd（PPh 3）2 Cl 2是关键催化剂，因为它的加入大大提高了反应速度，并在数分钟内干净地得到了产物。超过30种底物已成功转化为所需化合物，且收率大多为中度到良好。

  DOI：

  10.1021/acs.orglett.9b00053
• 作为产物：
  描述：

  (2-甲基苯甲酰)乙酸乙酯 在 sodium tetrahydroborate 作用下， 生成 3-羟基-3-(2-甲基苯基)丙酸乙酯
  参考文献：
  名称：

  Deracemisation of β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330: substrate specificity and mechanistic investigation

  摘要：

  Deracemisation of aryl substituted beta-hydroxy esters by immobilised whole cells of Candida parapsilosis ATCC 7330 gave > 99% ee and up to 75% yield of their corresponding (S)-enantiomers. Mechanistic investigation of the deracemisation reaction carried out using a deuterated substrate, ethyl 3-deutero-3-hydroxy-3-phenyl propanoate revealed that while the (S)-enantiomer remains unreacted the (R)enantiomer undergoes enantioselective oxidation to its corresponding ketoester, which on complementary enantiospecific reduction gives the (S)-enantiomer in high yield and % ee. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.045

文献信息

• N-Heterocyclic carbene mediated Reformatsky reaction of aldehydes with α-trimethylsilylcarbonyl compounds
  作者：Xiao-Lei Zou、Guang-Fen Du、Wan-Fu Sun、Lin He、Xiao-Wei Ma、Cheng-Zhi Gu、Bin Dai

  DOI：10.1016/j.tet.2012.11.015

  日期：2013.1

  N-Heterocyclic carbenes have been employed as highly efficient organocatalysts to mediate silyl-Reformatsky type reaction. In the presence of only 0.5 mol % nucleophilic carbene 1, various aldehydes coupled with α-trimethylsilylethylacetate very smoothly in DMF at room temperature to provide the corresponding β-hydroxyesters in moderate to high yields. α-Trimethylsilylketone and α-trimethylsilylamide

  N-杂环卡宾已被用作高效的有机催化剂，以介导甲硅烷基-Reformatsky型反应。在仅0.5mol％亲核卡宾1的存在下，各种醛与α-三甲基甲硅烷基乙基乙酸乙酯在室温下在DMF中非常平滑地偶联，以中等至高产率提供相应的β-羟基酯。α-三甲基甲硅烷基酮和α-三甲基甲硅烷基酰胺也可以进行加成反应，以中等收率得到β-羟基酮和β-羟基酰胺。
• The Use of Chiral BINAM NHC-Rh(III) Complexes in Enantioselective Hydrosilylation of 3-Oxo-3-arylpropionic Acid Methyl or Ethyl Esters
  作者：Qin Xu、Xingxing Gu、Sijia Liu、Qinyu Dou、Min Shi

  DOI：10.1021/jo062453d

  日期：2007.3.1

  Axially chiral BINAM N-heterocyclic carbene (NHC)-Rh(III) complexes were applied in the enantioselective hydrosilylation of 3-oxo-3-arylpropionic acid methyl or ethyl esters. The reduction products 3-hydroxy-3-arylpropionic acid methyl or ethyl esters could be obtained in good yields with good to excellent enantioselectivities under mild conditions.

  轴向手性BINAM N-杂环卡宾（NHC）-Rh（III）配合物用于3-氧代-3-芳基丙酸甲酯或乙酯的对映选择性氢化硅烷化。还原产物3-羟基-3-芳基丙酸甲酯或乙酯可以在温和的条件下以良好的收率获得良好的对映选择性。
• PROCESS FOR PRODUCING FUSED IMIDAZOLE COMPOUND, REFORMATSKY REAGENT IN STABLE FORM, AND PROCESS FOR PRODUCING THE SAME
  申请人：Kawakami Jun-ichi

  公开号：US20120077985A1

  公开（公告）日：2012-03-29

  The present invention provides an industrially advantageous process for producing a steroid C 17,20 lyase inhibitor represented by the general formula (I); and a Reformatsky reagent in a stable form suitable for the process. In the present invention, a compound represented by the general formula (I) is produced by reducing a specific β-hydroxy ester compound derivative or a salt thereof obtained from a specific carbonyl compound in a Reformatsky reaction in the presence of a metal hydride complex and a metal halide, and then subjecting it to a ring-closing reaction. In the above Reformatsky reaction, it is useful to use a stable solution of a compound represented by the general formula BrZnCH 2 COOC 2 H 5 or a crystal of the compound which is represented by the formula (BrZnCH 2 COOC 2 H 5 .THF) 2 .

  本发明提供了一种工业上有利的制备类固醇C17,20裂解酶抑制剂的方法，其通式表示为(I)；以及适用于该方法的稳定形式的Reformatsky试剂。在本发明中，通过在金属氢化物复合物和金属卤化物的存在下还原从特定羰基化合物获得的特定β-羟基酯化合物衍生物或其盐，然后将其进行环合反应，从而制备出通式(I)所表示的化合物。在上述的Reformatsky反应中，使用通式为BrZnCH2COOC2H5的化合物的稳定溶液或者通式为(BrZnCH2COOC2H5.THF)2的化合物的晶体是有用的。
• Steric effects in the enantioselective transfer hydrogenation of 2-aroylacetates
  作者：Kathelyne Everaere、Jean-François Carpentier、André Mortreux、Michel Bulliard

  DOI：10.1016/s0957-4166(99)00540-6

  日期：1999.12

  Benzoylacetate esters and aryl-substituted derivatives are efficiently reduced in 2-propanol using the readily available catalytic combination (1S,2R)-ephedrine/[RuCl2(eta(6)-p-cymene)](2) to give the corresponding alcohols in high yields and enantioselectivities (up to 94% ee). (C) 2000 Elsevier Science Ltd. All rights reserved.
• AYI A. I.; CONDOM R.; WADE T. N.; GUEDJ R., J. FLUOR. CHEM., 1979, 14, NO 6, 437-454
  作者：AYI A. I.、 CONDOM R.、 WADE T. N.、 GUEDJ R.

  DOI：——

  日期：——