(1S,2'S,3'S)-1-{3-[2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl]oxiran-2-yl}propanol | 177190-87-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2'S,3'S)-1-{3-[2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl]oxiran-2-yl}propanol
• CAS: 177190-87-3
• 化学式: C₁₄H₂₆O₄
• 分子量: 258.358
• InChiKey: GOCOMACNHAHAKD-SRVKXCTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.22
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2'S,3'S)-1-{3-[2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl]oxiran-2-yl}propanol 在 氢氧化钾 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.5h， 生成 (1R,2'S,3'S)-1-{3-[2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl]oxiran-2-yl}propanol
  参考文献：
  名称：

  Identification and synthesis of new bicyclic acetals from the mountain pine beetle, Dendroctonus ponderosae hopkins (Col.: Scol.)

  摘要：

  Head-space volatiles obtained from male mountain pine beetles, Dendroctonus ponderosae, were analyzed by coupled CC-MS and chiral gas chromatography. 5-Ethyl-7-methyl-6,8-dioxabicyclo[3.2.1] (6) was found as a new naturally occurring isomer of brevicomin (1). In addition, several stereoisomers of 7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1] (11) and 1-(5-methyl-6,8-dioxabicyclo[3.2.1]octyl)ethanol (12) could be identified. Relative and absolute configurations of the compounds were determined by unambiguous syntheses, which are described. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00013-2
• 作为产物：
  描述：

  (4E)-7-(2,5,5-trimethyl-1,3-dioxan-2-yl)-4-hepten-3-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-diisopropyl tartrate 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以88%的产率得到(1S,2'S,3'S)-1-{3-[2-(2,5,5-trimethyl-1,3-dioxan-2-yl)ethyl]oxiran-2-yl}propanol
  参考文献：
  名称：

  Identification and synthesis of new bicyclic acetals from the mountain pine beetle, Dendroctonus ponderosae hopkins (Col.: Scol.)

  摘要：

  Head-space volatiles obtained from male mountain pine beetles, Dendroctonus ponderosae, were analyzed by coupled CC-MS and chiral gas chromatography. 5-Ethyl-7-methyl-6,8-dioxabicyclo[3.2.1] (6) was found as a new naturally occurring isomer of brevicomin (1). In addition, several stereoisomers of 7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1] (11) and 1-(5-methyl-6,8-dioxabicyclo[3.2.1]octyl)ethanol (12) could be identified. Relative and absolute configurations of the compounds were determined by unambiguous syntheses, which are described. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00013-2