trans,trans-2,6-dimethyl-2,6-octadiene-1,8-diol diacetate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: trans,trans-2,6-dimethyl-2,6-octadiene-1,8-diol diacetate
• 英文别名: [(2E,6Z)-8-acetyloxy-3,7-dimethylocta-2,6-dienyl] acetate
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: PJAHPEXZNWUNLF-OHJCXFAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans,trans-2,6-dimethyl-2,6-octadiene-1,8-diol diacetate 在 ruthenium(IV) oxide 、 sodium periodate 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 0.07h， 以63%的产率得到Acetic acid (R)-2-[(2R,5S)-5-((R)-2-acetoxy-1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-2-hydroxy-ethyl ester
  参考文献：
  名称：

  Improved RuO4-catalysed oxidative cyclisation of geraniol-type 1,5-dienes to cis-2,5-bis(hydroxymethyl)tetrahydrofuranyldiols

  摘要：

  The oxidation of some representative 1,5-dienes based on the geraniol and nerol carbon skeletons, namely geranyl acetate (1), geranic acid methyl ester (5), trans,trans-2,6-dimethyl-2,6-octadiene-1,8-diol diacetate (9), neryl acetate (13) and neroic acid methyl ester (16), has been performed using catalytic amounts of RuO4 (from RuO2. 2H(2)O, 4%) in the presence of NaIO4 (4 equiv.) as co-oxidant in the solvent mixture EtOAc/CH3CN/H2O (3:3:1) at 0 degreesC for 4 min. These conditions assure a degree of stereoselectivity for the geraniol-type dienes higher than that obtained under the Sharpless conditions [RuCl3. (H2O)(n) (2.2%). NaIO4 (3.1 equiv), CCl4/CH3CN/H2O (2:2:3), 0 degreesC], furnishing the cis- and trans-THF diol products in 62-70 and 6-9% yields, respectively. In addition, the: amount of the tis-THF, C-2 overoxidised, product is strongly reduced (2 7%). A comparison with the related MnO4--induced process, tested on the same substrates, was made. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00790-0