(3R,5R)-1,7-diphenyl-3,5-heptanediol | 103729-38-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (3R,5R)-1,7-diphenyl-3,5-heptanediol
• 英文别名: (3R,5R)-1,7-diphenylheptane-3,5-diol；3,5-dihydroxy-1,7-diphenylheptane；1,7-diphenylheptane-3,5-diol
• CAS: 103729-38-0
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: QSUSPILNZCEGPK-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  2,4-戊二酮,1,5-二氯 在 [RuCl₂-((R)-binap)]*NEt₃ 氢氧化钾 、 三氟化硼乙醚 、 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， -78.0~102.0 ℃ 、8.62 MPa 条件下， 反应 0.42h， 生成 (3R,5R)-1,7-diphenyl-3,5-heptanediol
  参考文献：
  名称：

  Optically pure 1,3-diols from (2R,4R)- and (2S,4S)-1,2:4,5-diepoxypentane

  摘要：

  Optically pure (> 97% ee) (2R,4R)-1,2:4,5-diepoxypentane (1) and its enantiomer can be prepared in three steps from 2,4-pentanedione without the need for chromatographic purification. Diepoxide 1 is an efficient precursor to a wide variety of optically pure syn and anti 1,3-diols. Reaction with excess nucleophile gives symmetric[GRAPHICS]anti 1,3-diols in good yield. Reaction with a slight excess of alkyllithium under Ganem's conditions gives the monoepoxides 5 in good yield. Addition of a second nucleophile to monoepoxide 5 gives asymmetric anti 1,3-diols. Mitsunobu inversion of monoepoxide 5 followed by addition of a second nucleophile gives syn 1,3-diols. Optically pure syn and anti 1,3-diols are available from diepoxide 1 in one to three steps and good overall yield.

  DOI：

  10.1021/jo00017a032

文献信息

• Hashimoto, Toshihiro; Tori, Motoo; Asakawa, Yoshinori, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 4, p. 1846 - 1849
  作者：Hashimoto, Toshihiro、Tori, Motoo、Asakawa, Yoshinori

  DOI：——

  日期：——
• Optically pure 1,3-diols from (2R,4R)- and (2S,4S)-1,2:4,5-diepoxypentane
  作者：Scott D. Rychnovsky、George Griesgraber、Sam Zeller、Donald J. Skalitzky

  DOI：10.1021/jo00017a032

  日期：1991.8

  Optically pure (> 97% ee) (2R,4R)-1,2:4,5-diepoxypentane (1) and its enantiomer can be prepared in three steps from 2,4-pentanedione without the need for chromatographic purification. Diepoxide 1 is an efficient precursor to a wide variety of optically pure syn and anti 1,3-diols. Reaction with excess nucleophile gives symmetric[GRAPHICS]anti 1,3-diols in good yield. Reaction with a slight excess of alkyllithium under Ganem's conditions gives the monoepoxides 5 in good yield. Addition of a second nucleophile to monoepoxide 5 gives asymmetric anti 1,3-diols. Mitsunobu inversion of monoepoxide 5 followed by addition of a second nucleophile gives syn 1,3-diols. Optically pure syn and anti 1,3-diols are available from diepoxide 1 in one to three steps and good overall yield.