5-(2S,4S)-2,4-dihydroxyheptyl-7-methoxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one | 1394226-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 5-(2S,4S)-2,4-dihydroxyheptyl-7-methoxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one
• 英文别名: 5-[(2S,4S)-2,4-dihydroxyheptyl]-7-methoxy-2,2-dimethyl-1,3-benzodioxin-4-one
• CAS: 1394226-65-3
• 化学式: C₁₈H₂₆O₆
• 分子量: 338.401
• InChiKey: DWDSVUXHPDYPHK-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(2S,4S)-2,4-dihydroxyheptyl-7-methoxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以75%的产率得到(S)-8-hydroxy-3-[(S)-2-hydroxypentyl]-6-methoxyisochroman-1-one
  参考文献：
  名称：

  Total Synthesis of 7-Deoxy-6-O-methylfusarentin Featuring a Chelation-Controlled 1,3-Reetz–Keck-Type Allylation

  摘要：

  The total synthesis of 7-deoxy-6-O-methylfiisarentin (1) and a formal synthesis of 7-deoxy-6,8-O-dimethylfusarentin (2) has been successfully achieved in 10 steps. The described tactic underscores a diastereoselective strategy which incorporates a single acyclic reaction based on the initial stereocenter by means of a 1,3-chelation-controlled Reetz-Keck-type allylation.

  DOI：

  10.1021/jo301167a
• 作为产物：
  描述：

  5-hydroxy-7-methoxy-2,2-dimethyl-benzo[1,3]dioxin-4-one 在 吡啶 、 四(三苯基膦)钯 、 氢气 、 palladium(II) hydroxide 、 magnesium oxide 、 四氯化钛 、 臭氧 、 cesium fluoride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 苯 为溶剂， -78.0~83.0 ℃ 、101.33 kPa 条件下， 反应 79.67h， 生成 5-(2S,4S)-2,4-dihydroxyheptyl-7-methoxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one
  参考文献：
  名称：

  Total Synthesis of 7-Deoxy-6-O-methylfusarentin Featuring a Chelation-Controlled 1,3-Reetz–Keck-Type Allylation

  摘要：

  The total synthesis of 7-deoxy-6-O-methylfiisarentin (1) and a formal synthesis of 7-deoxy-6,8-O-dimethylfusarentin (2) has been successfully achieved in 10 steps. The described tactic underscores a diastereoselective strategy which incorporates a single acyclic reaction based on the initial stereocenter by means of a 1,3-chelation-controlled Reetz-Keck-type allylation.

  DOI：

  10.1021/jo301167a

文献信息

• Total Synthesis of 7-Deoxy-6-<i>O</i>-methylfusarentin Featuring a Chelation-Controlled 1,3-Reetz–Keck-Type Allylation
  作者：Timothy N. Trotter、Aymara M. M. Albury、Michael P. Jennings

  DOI：10.1021/jo301167a

  日期：2012.9.7

  The total synthesis of 7-deoxy-6-O-methylfiisarentin (1) and a formal synthesis of 7-deoxy-6,8-O-dimethylfusarentin (2) has been successfully achieved in 10 steps. The described tactic underscores a diastereoselective strategy which incorporates a single acyclic reaction based on the initial stereocenter by means of a 1,3-chelation-controlled Reetz-Keck-type allylation.