1-(1,3-dioxolan-2-yl)-4-phenyl-butan-2-ol

• 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: 1-(1,3-dioxolan-2-yl)-4-phenyl-butan-2-ol
• 英文别名: (2R)-1-(1,3-dioxolan-2-yl)-4-phenylbutan-2-ol
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: DQTWJOWHLUQASJ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯丙醛 、 2-乙烯氧基乙醇 在 4 A molecular sieve 三异丙氧基氯化钛 、 (R)-1,1'-Bi-2-naphthol 、 sodium hydride 作用下， 以 正己烷 、 甲苯 为溶剂， 以62%的产率得到1-(1,3-dioxolan-2-yl)-4-phenyl-butan-2-ol
  参考文献：
  名称：

  High enantio- and diastereoselective induction of BINOL- and TADDOL-modified vinyloxy ethoxides in C–C coupling reactions with aldehydes

  摘要：

  The basic reagent vinyloxyethoxy titanium trisisopropyloxide, easily modified by replacing two of the isopropyloxides with the optically active diol (R)- or (S)-BINOL, reacts with simple, prochiral aldehydes to give chiral beta-hydroxy-1,3-dioxolanes with enantiomeric ratios up to 99:1. The same reagents, (R)- or (S)-configured, react with the chiral 2,3-O-isopropylidene-D-glyceraldehyde to give the corresponding open chain pentose derivatives. The main components have opposite descriptors at the newly created stereogenic center, indicating strong reagent control. A comparable system, modified by (R,R)- or (S,S)-TADDOL shows a weaker induction with the chiral aldehyde, but now with the same product configuration for both reagents, indicating predominant substrate control. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.001