(4S,5R)-4-(bromomethyl)-5-heptyl-2,2-dimethyl-1,3-dioxolane | 546084-19-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-4-(bromomethyl)-5-heptyl-2,2-dimethyl-1,3-dioxolane
• CAS: 546084-19-9
• 化学式: C₁₃H₂₅BrO₂
• 分子量: 293.244
• InChiKey: VBXDCGDDGHUSLC-VXGBXAGGSA-N

物化性质

• 沸点：
  315.2±27.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-(bromomethyl)-5-heptyl-2,2-dimethyl-1,3-dioxolane 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 (2R,3R)-1,2-epoxy-3-decanol
  参考文献：
  名称：

  Straightforward Synthesis of Panaxytriol:  An Active Component of Red Ginseng

  摘要：

  A total synthesis of (3R,9R,10R)-panaxytriol (1) was accomplished enantioselectively (40% overall yield; 30% for the longest sequence). A key step was a Cadiot-Chodkiewicz cross-coupling reaction on two fragments containing, in the aggregate, three unprotected hydroxyl groups. One fragment was synthesized by a highly enantioselective reduction of an enynone. The other arose from a highly enantioselective dihydroxylation of an allylic alcohol.

  DOI：

  10.1021/jo0341665
• 作为产物：
  描述：

  反式-2-癸烯醇 在 咪唑 、 甲基磺酰胺 、 AD-mix-β 、 溴 、 对甲苯磺酸 、 三苯基膦 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 31.5h， 生成 (4S,5R)-4-(bromomethyl)-5-heptyl-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Straightforward Synthesis of Panaxytriol:  An Active Component of Red Ginseng

  摘要：

  A total synthesis of (3R,9R,10R)-panaxytriol (1) was accomplished enantioselectively (40% overall yield; 30% for the longest sequence). A key step was a Cadiot-Chodkiewicz cross-coupling reaction on two fragments containing, in the aggregate, three unprotected hydroxyl groups. One fragment was synthesized by a highly enantioselective reduction of an enynone. The other arose from a highly enantioselective dihydroxylation of an allylic alcohol.

  DOI：

  10.1021/jo0341665

文献信息

• Straightforward Synthesis of Panaxytriol:  An Active Component of Red Ginseng
  作者：Heedong Yun、Samuel J. Danishefsky

  DOI：10.1021/jo0341665

  日期：2003.5.1

  A total synthesis of (3R,9R,10R)-panaxytriol (1) was accomplished enantioselectively (40% overall yield; 30% for the longest sequence). A key step was a Cadiot-Chodkiewicz cross-coupling reaction on two fragments containing, in the aggregate, three unprotected hydroxyl groups. One fragment was synthesized by a highly enantioselective reduction of an enynone. The other arose from a highly enantioselective dihydroxylation of an allylic alcohol.