2,4-dimethylhex-4-ene-2,3-(R)-diol | 132312-00-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-dimethylhex-4-ene-2,3-(R)-diol
• 英文别名: (R)-2,4-dimethylhex-4-ene-2,3-diol；(3R)-2,5-dimethylhex-4-ene-2,3-diol
• CAS: 132312-00-6
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: STIDYKNBYLYCLV-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  2,4-dimethylhex-4-ene-2,3-(R)-diol 在 吡啶 、 正丁基锂 、 四氯化钛 、 对甲苯磺酸 、 臭氧 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 86.0h， 生成 2,2-dimethyl-3-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)cyclopropane-1,1-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Hemisynthesis of methyl pyrethroates from γ-alkoxy-alkylidene malonates and isopropylidenediphenylsulfurane and isopropylidenetriphenylphosphorane

  摘要：

  Hemi synthesis of methyl pyrethroates from gamma-alkoxy-alkylidene malonates and isopropylidenediphenylsulfurane and isopropylidenetriphenylphosphorane is disclosed. It takes advantage of the high degree of stereocontrol observed in the cyclopropanation of gamma-alkoxy-alkylidene malonates by the above mentioned ylides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.035
• 作为产物：
  描述：

  2,5-二甲基-2,4-己二烯 在 甲基磺酰胺 、 AD-mix β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 20.0h， 以78%的产率得到2,4-dimethylhex-4-ene-2,3-(R)-diol
  参考文献：
  名称：

  Enantioselective syntheses of the assigned structures of the helibisabonols A and B

  摘要：

  The enantioselective syntheses of the compounds with the assigned structures of the helibisabonols A and B have been accomplished. Using an enzymatic desymmetrization of the sigma-symmetrical diol (route a) and a diastereoselective conjugate addition of the methyl to the enone with a chiral auxiliary (route b) we constructed the key tertiary stereogenic center at the benzylic position (C7) and then used an asymmetric dihydroxylation for assembling the C10 stereogenic center. In addition, possible diastereoisomers of the natural products were prepared and detailed comparisons of the H-1 and C-13 NMR spectra were conducted. As a result, the structure originally assigned to helibisabonol A may be revised to (7R,10R)-1. In the case of helibisabonol B, the (7R,10R)-2 would be reasonable based on a comparison of the NMR data and the biogenetic parallelism with helibisabonol A. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.064

文献信息

• Bicyclic Peroxides and Perorthoesters with 1,2,4-Trioxane Structures
  作者：Axel G. Griesbeck、Dirk Blunk、Tamer T. El-Idreesy、Angela Raabe

  DOI：10.1002/anie.200701397

  日期：2007.11.26
• Xu, Daqiang; Crispino, Gerard A.; Sharpless, K. Barry, Journal of the American Chemical Society, 1992, vol. 114, # 19, p. 7570 - 7571
  作者：Xu, Daqiang、Crispino, Gerard A.、Sharpless, K. Barry

  DOI：——

  日期：——