2-[(3R,6R)-6-甲基-6-(4-甲基苯基)二恶烷-3-基]丙-2-醇 | 162302-88-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[(3R,6R)-6-甲基-6-(4-甲基苯基)二恶烷-3-基]丙-2-醇
• 英文名称: (8S,12R)-Yingzhoosu C
• 英文别名: (8S,12R)-yingzhaosu C；2-[(3R,6S)-6-methyl-6-(4-methylphenyl)dioxan-3-yl]propan-2-ol
• CAS: 162302-88-7；121067-52-5
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: FCQCSKGBKUYFSW-HIFRSBDPSA-N

物化性质

• 比旋光度：
  D14 +2.89° (c = 2.15 in methanol); D +189.3° (c = 0.93 in CHCl3); D -185.4° (c = 0.78 in CHCl3)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-((3R,6S)-6-Methyl-6-p-tolyl-[1,2]dioxan-3-yl)-prop-2-yl-hydroperoxide 在 三苯基膦 作用下， 以 苯 为溶剂， 反应 1.0h， 以94%的产率得到2-[(3R,6R)-6-甲基-6-(4-甲基苯基)二恶烷-3-基]丙-2-醇
  参考文献：
  名称：

  Concise synthesis of yingzhaosu C and epi-yingzhaosu C by peroxyl radical cyclization. Assignment of relative configuration

  摘要：

  The antimalarial peroxide yingzhaosu C and its diastereoisomer (epi-yingzhaosu C) have been synthesized by means of tandem peroxyl radical cyclization-oxygen entrapment. The relative configuration of yingzhaosu C is assigned as cis (3) on account of NMR data for both diastereoisomers, (2) and (3), and their precursors (8) and (9).

  DOI：

  10.1016/0040-4039(95)00714-n

文献信息

• Enantioselective Total Syntheses and Stereochemical Studies of All Four Stereoisomers of Yingzhaosu C
  作者：Xing-Xiang Xu、Han-Qing Dong

  DOI：10.1021/jo00115a019

  日期：1995.5

  The enantioselective total syntheses and the stereochemistry of all four stereoisomers of yingzhaosu C, an antimalarial peroxy-containing sesquiterpene isolated from yingzhao [Artabotrys uncinatus (L.) Merr.], are described. The key to the syntheses was the combination of Sharpless asymmetric epoxidation and the intramolecular nucleophilic epoxy-opening with a benzylic peroxy group to construct the 1,2-dioxane skeleton. The configurations of the 1,2-dioxanes in four stereoisomers were assigned by spectroscopy and chemical transformation.
• Concise synthesis of yingzhaosu C and epi-yingzhaosu C by peroxyl radical cyclization. Assignment of relative configuration
  作者：John Boukouvalas、Roxane Pouliot、Yvon Fréchette

  DOI：10.1016/0040-4039(95)00714-n

  日期：1995.6

  The antimalarial peroxide yingzhaosu C and its diastereoisomer (epi-yingzhaosu C) have been synthesized by means of tandem peroxyl radical cyclization-oxygen entrapment. The relative configuration of yingzhaosu C is assigned as cis (3) on account of NMR data for both diastereoisomers, (2) and (3), and their precursors (8) and (9).