methyl 3-(p-chlorophenyl)-3-hydroxy-2-methylpropionate

• 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: methyl 3-(p-chlorophenyl)-3-hydroxy-2-methylpropionate
• 英文别名: Methyl 3-(p-chlorophenyl)-3-hydroxy-2-methyl-propionate；methyl 3-(4-chlorophenyl)-3-hydroxy-2-methylpropanoate
• 化学式: C₁₁H₁₃ClO₃
• 分子量: 228.675
• InChiKey: DJTXJRMVTPOVOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-[(4-氯苯基)-羟基甲基]-丙烯酸甲酯 在 2-碘酰基苯甲酸 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 108.0h， 生成 methyl 3-(p-chlorophenyl)-3-hydroxy-2-methylpropionate
  参考文献：
  名称：

  Regio- and enantioselective bioreduction of methyleneketoesters using both polymeric resin and cellulose matrix

  摘要：

  Methyleneketoesters were prepared in >90% yield by performing an IBX oxidation of Morita-Baylis-Hillman adducts. A methodology was developed to achieve methyl 3-aryl-3-keto-2-methylenepropanoate reduction using a screening of yeast strains in three different reaction procedures to obtain products with both high yield and diastereoselectivity. The reactions conducted in water provided inferior yields (50%) for substrates 2b-c. Employing Amberlite (R) XAD7HP which was a substrate reservoir that also immediately extracted the products from the reaction medium after their formation, syn-4a-c and anti-4a-c were isolated in 60-70% yield, with high stereoselectivity (98-99% ee). The best results were obtained using substrates adsorbed on filter paper which provided products yields above 70%, a 99% ee and a diastereomoeric ratio (syn-4: anti-4) 9:1. Cellulose matrix has excellent potential to be successfully employed in general biocatalytic reactions. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.09.018

文献信息

• Ligand-Promoted, Boron-Mediated Chemoselective Carboxylic Acid Aldol Reaction
  作者：Hideoki Nagai、Yuya Morita、Yohei Shimizu、Motomu Kanai

  DOI：10.1021/acs.orglett.6b00914

  日期：2016.5.6

  selective aldol reaction mediated by boron compounds and a mild organic base (DBU) was developed. Inclusion of electron-withdrawing groups in the amino acid derivative ligands reacted with BH3·SMe2 forms a boron promoter with increased Lewis acidity at the boron atom and facilitated the carboxylic acid selective enolate formation, even in the presence of other carbonyl groups such as amides, esters, ketones

  开发了由硼化合物和温和的有机碱（DBU）介导的第一个羧酸选择性羟醛反应。与BH 3 ·SMe 2反应的氨基酸衍生物配体中包含吸电子基团，形成硼促进剂，在硼原子上路易斯酸度增加，即使在存在其他羰基如酰胺，酯，酮或脂族醛。出色的配体效应导致了包括生物相关化合物在内的广泛底物范围。
• An efficient stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes from unactivated Baylis–Hillman adducts using NaBH4/CuCl2·2H2O
  作者：Biswanath Das、Joydeep Banerjee、Anjoy Majhi、Gurram Mahender

  DOI：10.1016/j.tetlet.2004.10.088

  日期：2004.12

  A convenient and facile stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes has been achieved by treatment of unactivated Baylis–Hillman adducts with NaBH4 in the presence of CuCl2·2H2O at room temperature for 15 min.

  在室温下，在CuCl 2 ·2H 2 O存在下，用NaBH 4处理未活化的Baylis-Hillman加合物，可以实现便捷而又简便的立体选择合成（E）-和（Z）-三取代烯烃。
• ——
  作者：A. B. Terent'ev、T. T. Vasil'eva、N. A. Kuz'mina、N. E. Mysova、O. V. Chakhovskaya

  DOI：10.1023/a:1013175403637

  日期：——

  Pentacarbonyliron promotes addition of alpha-halocarboxylic acid esters at the carbonyl group of benzaldehyde and its para-substituted analogs. The substituent in the benzene ring strongly affects the process.
• Reductive aldol-type reaction of α,β-unsaturated esters with aldehydes or ketones in the presence of Rh catalyst and Et2Zn
  作者：Kazuyuki Sato、Motoyuki Isoda、Yoriko Tokura、Keiko Omura、Atsushi Tarui、Masaaki Omote、Itsumaro Kumadaki、Akira Ando

  DOI：10.1016/j.tetlet.2013.08.109

  日期：2013.10

  The reaction of RhCl(PPh3)(3) with Et2Zn easily generated a rhodium-hydride complex (Rh-H) that added to alpha,beta-unsaturated esters to form rhodium enolate complexes by formal 1,4-reduction. These rhodium enolates gave the corresponding Reformatslcy-type reagents through transmetalation, and they reacted with various aldehydes and ketones to give reductive aldol-type products in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Regio- and enantioselective bioreduction of methyleneketoesters using both polymeric resin and cellulose matrix
  作者：Michel R.B. Chaves、Paulo J.S. Moran、J. Augusto R. Rodrigues

  DOI：10.1016/j.molcatb.2013.09.018

  日期：2013.12

  Methyleneketoesters were prepared in >90% yield by performing an IBX oxidation of Morita-Baylis-Hillman adducts. A methodology was developed to achieve methyl 3-aryl-3-keto-2-methylenepropanoate reduction using a screening of yeast strains in three different reaction procedures to obtain products with both high yield and diastereoselectivity. The reactions conducted in water provided inferior yields (50%) for substrates 2b-c. Employing Amberlite (R) XAD7HP which was a substrate reservoir that also immediately extracted the products from the reaction medium after their formation, syn-4a-c and anti-4a-c were isolated in 60-70% yield, with high stereoselectivity (98-99% ee). The best results were obtained using substrates adsorbed on filter paper which provided products yields above 70%, a 99% ee and a diastereomoeric ratio (syn-4: anti-4) 9:1. Cellulose matrix has excellent potential to be successfully employed in general biocatalytic reactions. (C) 2013 Elsevier B.V. All rights reserved.