anti-1-phenyl-1,3-pentanediol

• 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: anti-1-phenyl-1,3-pentanediol
• 英文别名: (1R,3S)-1-phenylpentane-1,3-diol
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: BOIHAPODUXHNBA-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-羟基-1-苯基戊-1-酮 在 diisopropoxytitanium(III) tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 syn-1-phenyl-1,3-pentanediol 、 anti-1-phenyl-1,3-pentanediol
  参考文献：
  名称：

  Diastereoselectivity in the Reduction of Acyclic Carbonyl Compounds with Diisopropoxytitanium(III) Tetrahydroborate

  摘要：

  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.

  DOI：

  10.1021/jo9902906

文献信息

• Diastereoselective reduction of β-hydroxyketones with amineboranes in the presence of lithium perchlorate
  作者：Chatla Narayana、M.Rama Reddy、Max Hair、George W Kabalka

  DOI：10.1016/s0040-4039(97)10030-2

  日期：1997.11

  The reduction of beta-hydroxyketones with amineboranes in the presence of lithium perchlorate produces the corresponding anti 1,3-diols as major products. (C) 1997 Elsevier Science Ltd.
• 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.