1,3-diphenyl-2,2-dimethylpropane-1,3-diol | 95581-19-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,3-diphenyl-2,2-dimethylpropane-1,3-diol
• 英文别名: syn-2,2-dimethyl-1,3-diphenyl-1,3-propanediol；meso-1,3-Diphenyl-2,2-dimethyl-1,3-propandiol；(1R,3S)-2,2-dimethyl-1,3-diphenylpropane-1,3-diol
• CAS: 95581-19-4
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: IMKKDASVJRQCLQ-IYBDPMFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯甲酸酐 、 1,3-diphenyl-2,2-dimethylpropane-1,3-diol 在 chiral phosphabicyclooctane derivative 作用下， 反应 8.0h， 生成 Benzoic acid (1S,3R)-3-hydroxy-2,2-dimethyl-1,3-diphenyl-propyl ester 、 3-hydroxy-2,2-dimethyl-1,3-diphenylpropyl benzoate
  参考文献：
  名称：

  Desymmetrization of meso-Hydrobenzoin Using Chiral, Nucleophilic Phosphine Catalysts

  摘要：

  The desymmetrization of meso-hydrobenzoin is described using chiral phosphine catalysts 8b-d and 9-11. The best enantioselectivity at room temperature was obtained with the newly synthesized phospholane 8c and benzoic anhydride, but the reaction is very slow. Much faster reactions, but somewhat lower enantioselectivities were observed using the bicyclic phosphine catalyst 9. To obtain product 5a with >90% ee required conditions where the ee is upgraded due to the formation of the dibenzoate 6a. Among the new phospholane catalysts, 8b has the best selectivity in the kinetic resolution of benzylic alcohols, but not at the level observed previously with catalyst 11.

  DOI：

  10.1021/jo030279c
• 作为产物：
  描述：

  2,2-二甲基-1,3-二苯基丙烷-1,3-二酮 在 锂硼氢 、 四氯化钛 作用下， 以 乙醚 为溶剂， 以8%的产率得到d,l-1,3-Diphenyl-2,2-dimethyl-1,3-propandiol
  参考文献：
  名称：

  Maier, Guenther; Schmitt, Reinhart K.; Seipp, Ulrich, Chemische Berichte, 1985, vol. 118, # 2, p. 722 - 728

  摘要：

  DOI：

文献信息

• Diastereoselectivity in the Reduction of Acyclic Carbonyl Compounds with Diisopropoxytitanium(III) Tetrahydroborate
  作者：K. S. Ravikumar、Surajit Sinha、S. Chandrasekaran

  DOI：10.1021/jo9902906

  日期：1999.8.1

  Diisopropoxytitanium(III) tetrahydroborate, ((PrO)-Pr-i)(2)TiBH4, formed in situ in dichloromethane from diisopropoxytitanium dichloride and benzyltriethylammonium tetrahydroborate (1:2) reduces alpha-hydroxyketones/1,2-diketones and beta-hydroxyketones/1,3-diketones to the corresponding diols with high stereoselectivity. In the case of alpha-hydroxyketones and 1,2-diketones, the anti isomer is the major product while reduction of beta-hydroxyketones and 1,3-diketones leads to the syn isomer as the major product.
• Maier, Guenther; Schmitt, Reinhart K.; Seipp, Ulrich, Chemische Berichte, 1985, vol. 118, # 2, p. 722 - 728
  作者：Maier, Guenther、Schmitt, Reinhart K.、Seipp, Ulrich

  DOI：——

  日期：——
• MAIER, G.;SCHMITT, R. K.;SEIPP, U., CHEM. BER., 1985, 118, N 2, 722-728
  作者：MAIER, G.、SCHMITT, R. K.、SEIPP, U.

  DOI：——

  日期：——
• MAIER, G.;ROTH, C.;SCHMITT, R. K., CHEM. BER., 1985, 118, N 2, 704-721
  作者：MAIER, G.、ROTH, C.、SCHMITT, R. K.

  DOI：——

  日期：——
• Synthesis, resolution, and applications of 3-amino-2,2-dimethyl-1,3-diphenylpropan-1-ol, a conformationally restricted 1,3-aminoalcohol
  作者：M.N. Patil、R.G. Gonnade、N.N. Joshi

  DOI：10.1016/j.tet.2010.05.001

  日期：2010.7

  Efficient synthetic routes to both syn and anti diastereomers of a conformationally restricted 1,3-aminoalcohol were devised. Resolution of the aminoalcohols was accomplished through diastereomeric salt with R-(-)-O-acetyl mandelic acid. These aminoalcohols were examined as ligands for two standard reactions, namely, enantioselective addition of Et2Zn to aldehydes and reduction of prochiral ketones with BH3. (C) 2010 Elsevier Ltd. All rights reserved.