(2R,4R)-1,5-dibromo-2,4-pentanediol | 135943-82-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (2R,4R)-1,5-dibromo-2,4-pentanediol
• 英文别名: 2,4-pentanediol, 1,5-dibromo-, (2R,4R)-；(2R,4R)-1,5-dibromopentane-2,4-diol
• CAS: 135943-82-7
• 化学式: C₅H₁₀Br₂O₂
• 分子量: 261.941
• InChiKey: IZMILZILGRGOIM-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,4R)-1,5-dibromo-2,4-pentanediol 、 2,2-二甲氧基丙烷 在 camphor-10-sulfonic acid 作用下， 以 丙酮 为溶剂， 反应 13.0h， 以83%的产率得到(4R,6R)-4,6-bis(bromomethyl)-2,2-dimethyl-1,3-dioxane
  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
• 作为产物：
  描述：

  2,4-戊二酮,1,5-二氯 在 Ru2Cl4{2,2'-bis(diphenylphosphino)-1,1'-binaphthyl}2*N(C2H5)3 氢氧化钾 、 dilithium tetrabromonickelate(II) 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 25.0~102.0 ℃ 、8.62 MPa 条件下， 反应 9.0h， 生成 (2R,4R)-1,5-dibromo-2,4-pentanediol
  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

• Synthesis of a Key Building Block for a Butyrolactone → 1,3-Diol Approach to the Polyol Part of Roflamycoin
  作者：Diego Muñoz-Torrero、Reinhard Brückner

  DOI：10.1002/(sici)1099-0690(199806)1998:6<1031::aid-ejoc1031>3.0.co;2-d

  日期：1998.6

  Monoepoxide 33 – also derived from dichlorodiol 12 – was ring-opened with the same Gilman cuprate affording compound 35. It was transformed into the correctly protected γ-lactone 6 in seven steps, key reactions being the ozonolysis 35 36 and the diastereoselective reduction 36 anti-37.

  为了制备三（γ-内酯）3，从二氯二醇12（99.8%ee）合成单（γ-内酯）6。双环氧化物 9 – 衍生自二氯二醇 12 (99.8% ee) – 与来自 2-lithio-1,5-己二烯和 CuI 的 Gilman 铜酸盐开环，几乎完全得到单环氧化物 21；再经过五步，得到与目标分子6具有相同立体三联体但保护基不同的γ-内酯30。单环氧化物 33 - 也衍生自二氯二醇 12 - 用相同的吉尔曼铜酸盐开环，得到化合物 35。 它通过七个步骤转化为正确保护的 γ-内酯 6，关键反应是臭氧分解 35 36 和非对映选择性还原 36 反-37.
• 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.

表征谱图