2-[5-methyl-5-(oxiran-2-yl)oxolan-2-yl]propan-2-ol | 93780-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: 2-[5-methyl-5-(oxiran-2-yl)oxolan-2-yl]propan-2-ol
• CAS: 93780-28-0
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: QZRANJWXTXXQQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.99
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-[5-methyl-5-(oxiran-2-yl)oxolan-2-yl]propan-2-ol 在 copper(l) iodide 、 二异丙胺 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 32.0h， 生成 (R)-1-((2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)penta-3,4-dien-1-ol
  参考文献：
  名称：

  Total syntheses of the squalene-derived halogenated polyethers ent -dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades

  摘要：

  Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise the proposed biogeneses. Other common features found in the routes include convergent fragment coupling strategies to assemble the natural products' backbones and the use of epoxide-opening cascades for rapid constructions of the fused polyether subunits. Through de novo synthesis of armatol A, we elucidate the absolute and relative configuration of this natural product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.041
• 作为产物：
  描述：

  5,6-epoxy-6-methyl-2-heptanone 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-[5-methyl-5-(oxiran-2-yl)oxolan-2-yl]propan-2-ol
  参考文献：
  名称：

  从1,5-二烯到取代的双四氢呋喃的高度立体选择性的路线。

  摘要：

  在四个步骤（包括两个立体选择性环化）中，从香叶基氯和神经烷基氯获得具有四个手性中心的双-四氢呋喃1a和1b，其纯度为90％。

  DOI：

  10.1016/s0040-4039(01)92904-1

文献信息

• Total syntheses of the squalene-derived halogenated polyethers ent -dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades
  作者：Brian S. Underwood、Jessica Tanuwidjaja、Sze-Sze Ng、Timothy F. Jamison

  DOI：10.1016/j.tet.2013.04.041

  日期：2013.6

  Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise the proposed biogeneses. Other common features found in the routes include convergent fragment coupling strategies to assemble the natural products' backbones and the use of epoxide-opening cascades for rapid constructions of the fused polyether subunits. Through de novo synthesis of armatol A, we elucidate the absolute and relative configuration of this natural product. (C) 2013 Elsevier Ltd. All rights reserved.
• A highly stereoselective route to substituted bis-tetrahydrofurans from 1,5-dienes.
  作者：Roger Amouroux、Gabriel Folefoc、Francine Chastrette、Maurice Chastrette

  DOI：10.1016/s0040-4039(01)92904-1

  日期：——

  Bis-tetrahydrofurans 1a and 1b, containing four chiral centers, are obtained with a 90 % isomeric purity from geranyl and neryl chlorides in four steps including two stereoselective cyclizations.

  在四个步骤（包括两个立体选择性环化）中，从香叶基氯和神经烷基氯获得具有四个手性中心的双-四氢呋喃1a和1b，其纯度为90％。