(4R,5R)-2((1R)-1-hydroxy-1-methylhexyl)-4,5-diphenyl-1,3-dioxolane

• 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: (4R,5R)-2((1R)-1-hydroxy-1-methylhexyl)-4,5-diphenyl-1,3-dioxolane
• 英文别名: (2R)-2-[(4R,5R)-4,5-diphenyl-1,3-dioxolan-2-yl]heptan-2-ol
• 化学式: C₂₂H₂₈O₃
• 分子量: 340.463
• InChiKey: LXVCLXLVILGPLJ-KCZVDYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  jasminaldehyde 在 二甲基硫 、 碳酸氢钠 、 对甲苯磺酸 、 臭氧 作用下， 以 乙醚 、 甲苯 、 苯 为溶剂， 反应 0.17h， 生成 (4R,5R)-2((1R)-1-hydroxy-1-methylhexyl)-4,5-diphenyl-1,3-dioxolane
  参考文献：
  名称：

  Highly Diastereoselective Additions to Chiral α-Keto Acetals

  摘要：

  A general synthesis of (4R*,5R*)-2-acyl-4,5-diphenyl-1,3-dioxolanes and the addition of alkylmagnesium bromides to these compounds is described. The addition reactions occur with high diastereoselectivity (typical selectivity ca. 90:10). An example addition reaction carried out on an optically active acetal proves the sense of asymmetric induction for addition of organomagnesium reagents to these alpha-keto acetals. An explanation of the mechanism of asymmetric induction is given.

  DOI：

  10.1021/jo9701804

文献信息

• Highly Diastereoselective Additions to Chiral α-Keto Acetals
  作者：Kauser M. Akhoon、David C. Myles

  DOI：10.1021/jo9701804

  日期：1997.8.1

  A general synthesis of (4R*,5R*)-2-acyl-4,5-diphenyl-1,3-dioxolanes and the addition of alkylmagnesium bromides to these compounds is described. The addition reactions occur with high diastereoselectivity (typical selectivity ca. 90:10). An example addition reaction carried out on an optically active acetal proves the sense of asymmetric induction for addition of organomagnesium reagents to these alpha-keto acetals. An explanation of the mechanism of asymmetric induction is given.