3-(4-methoxyphenyl)-2-phenyl-2-hydroxypropanoic | 33951-39-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-(4-methoxyphenyl)-2-phenyl-2-hydroxypropanoic
• 英文别名: 2-hydroxy-3-(4-methoxy-phenyl)-2-phenyl-propionic acid；2-Hydroxy-3-(4-methoxy-phenyl)-2-phenyl-propionsaeure；α-Oxy-α-phenyl-β-(4-methoxy-phenyl)-propionsaeure；α-(4-Methoxy-benzyl)-mandelsaeure；Phenyl-(4-methoxy-benzyl)-glykolsaeure；p-Methoxybenzyl-phenylglycolsaeure；2-Hydroxy-3-(4-methoxyphenyl)-2-phenylpropanoic acid
• CAS: 33951-39-2
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: DFASBEVSSCPXTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  192.5-193.0 °C
• 沸点：
  432.9±40.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-2-phenyl-2-hydroxypropanoic 在 甲醇 、 sodium methylate 、 lead(II) oxide 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 20.0h， 生成 2,4-bis(4-methoxyphenyl)-1,3,5-triphenylpentane-1,5-dione
  参考文献：
  名称：

  Synthesis and structural study of benzamarones by X-ray and NMR spectroscopy

  摘要：

  In this work only one diastereomer of benzamarone (1,2,3,4,5-pentaphenylpentan-1,5-dione) 1 was isolated from tandem condensation/addition reaction between deoxybenzoin and benzaldehyde in alkaline medium and by Michael addition of deoxybenzoin to (E)-2-phenylchalcone. Compound 1 was investigated by single crystal X-ray diffraction: C35H28O2, Mr = 480.57, triclinic system, space group P1 with unit cell parameters a = 11.489(2), b = 11.669(2), c = 11.855(2) angstrom, alpha = 104.31(4), beta = 116.91(3), gamma = 98.96(3)degrees, V = 1305.6(4) angstrom(3), Z = 2, T = 25(2) degrees C, rho(calc) = 1.222 gr/cm(3), mu = 0.074 mm(-1). This study allowed us to assign the configuration 2R,4R/25.4S corresponding to the diastereomer racemate C (Fig. 1) due to the fact that the crystal structure exhibits two independent molecules in the unit cell. Data obtained using NMR spectroscopy [1D and 20 NMR] are agreement with those obtained by X-ray diffraction. By comparison of NMR data, the configuration corresponding to the diastereomer racemate C was assigned to other substituted benzamarones synthesized by us, which present two and three stereocenters in their structure. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2010.12.005
• 作为产物：
  描述：

  3-(4-甲氧基苯基)苯丙酮 在 sodium hydroxide 、 硝基苯 作用下， 以 水 为溶剂， 160.0 ℃ 、344.73 kPa 条件下， 反应 6.0h， 以57%的产率得到3-(4-methoxyphenyl)-2-phenyl-2-hydroxypropanoic
  参考文献：
  名称：

  使用硝基苯作为氧化剂从酮单步合成取代乳酸

  摘要：

  摘要描述了酮向 α,β-二取代乳酸的一步转化。

  DOI：

  10.1080/00397919608003575

文献信息

• Hutchins et al., Journal of the Chemical Society, 1938, p. 1882,1884
  作者：Hutchins et al.

  DOI：——

  日期：——
• Malkin; Robinson, Journal of the Chemical Society, 1925, vol. 127, p. 376
  作者：Malkin、Robinson

  DOI：——

  日期：——
• Drefahl et al., Chemische Berichte, 1958, vol. 91, p. 755,756
  作者：Drefahl et al.

  DOI：——

  日期：——
• Synthesis and structural study of benzamarones by X-ray and NMR spectroscopy
  作者：Jorge D. Mufato、Daniel R. Vega、José M. Aguirre、Diego J. de la Faba、Beatriz Lantaño

  DOI：10.1016/j.molstruc.2010.12.005

  日期：2011.2

  In this work only one diastereomer of benzamarone (1,2,3,4,5-pentaphenylpentan-1,5-dione) 1 was isolated from tandem condensation/addition reaction between deoxybenzoin and benzaldehyde in alkaline medium and by Michael addition of deoxybenzoin to (E)-2-phenylchalcone. Compound 1 was investigated by single crystal X-ray diffraction: C35H28O2, Mr = 480.57, triclinic system, space group P1 with unit cell parameters a = 11.489(2), b = 11.669(2), c = 11.855(2) angstrom, alpha = 104.31(4), beta = 116.91(3), gamma = 98.96(3)degrees, V = 1305.6(4) angstrom(3), Z = 2, T = 25(2) degrees C, rho(calc) = 1.222 gr/cm(3), mu = 0.074 mm(-1). This study allowed us to assign the configuration 2R,4R/25.4S corresponding to the diastereomer racemate C (Fig. 1) due to the fact that the crystal structure exhibits two independent molecules in the unit cell. Data obtained using NMR spectroscopy [1D and 20 NMR] are agreement with those obtained by X-ray diffraction. By comparison of NMR data, the configuration corresponding to the diastereomer racemate C was assigned to other substituted benzamarones synthesized by us, which present two and three stereocenters in their structure. (C) 2010 Elsevier B.V. All rights reserved.
• Single Step Synthesis of Substituted Lactic Acids from Ketones using Nitrobenzene as an Oxidant
  作者：P. S. Srinivasan、R. Mahesh、G. Venkateswara Rao、N. Kalyanam

  DOI：10.1080/00397919608003575

  日期：1996.6

  Abstract A single step conversion of ketones to α,β-disubstituted lactic acids is described.

  摘要描述了酮向 α,β-二取代乳酸的一步转化。