5-Iodo-2-methyl-2-pentenylethoxymethoxy methyl ether | 85764-97-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Iodo-2-methyl-2-pentenylethoxymethoxy methyl ether
• 英文别名: (Z)-5-iodo-1-(2-methoxyethoxymethoxy)-2-methylpent-2-ene
• CAS: 85764-97-2
• 化学式: C₁₀H₁₉IO₃
• 分子量: 314.164
• InChiKey: PNWHLOLSQSAYHK-WMZJFQQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Iodo-2-methyl-2-pentenylethoxymethoxy methyl ether 在 lithium aluminium tetrahydride 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 六甲基磷酰三胺 、 乙醚 、 正己烷 为溶剂， 反应 6.33h， 生成 (+/-)-2-exo-(5-Methoxyethoxymethoxy-4-methylpent-3-enyl)-2-methyl-3-methylene-7-oxabicyclo<2.2.1>heptane
  参考文献：
  名称：

  Buchbauer, Gerhard; Lebada, Philippine; Spreitzer, Helmut, Liebigs Annalen, 1995, # 9, p. 1693 - 1696

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-1-Iodo-3-(2-methoxy-ethoxymethoxy)-2-methyl-propene 在 正丁基锂 作用下， 生成 5-Iodo-2-methyl-2-pentenylethoxymethoxy methyl ether
  参考文献：
  名称：

  合成立体选择性DU（±）-β-檀香醇

  摘要：

  我们在这里描述了（±）-β-檀香醇的一种新的收敛和立体选择性合成。该合成在最后一步涉及使用甲苯磺酸吡啶鎓对甲氧基乙氧基甲基醚的原始脱保护方法。

  DOI：

  10.1016/s0040-4039(00)85888-8

文献信息

• Synthesis and olfactoric activity of keto-β-santalol and methoxy-β-santalol
  作者：Gerhard Buchbauer、Helmut Spreitzer、Friederike Zechmeister-Machhart、Alexander Klinsky、Petra Weiβ-Greiler、Peter Wolschann

  DOI：10.1016/s0223-5234(98)80047-0

  日期：1998.6

  In extension of structure-activity relationship investigations on beta-santalol, where the shape of the molecular surface was found to be of high importance, the influence of the electrostatic properties cf the molecules was investigated. Two derivatives of beta-santalol with similar molecular shape but with an oxygen atom instead of carbon atoms were synthesized: keto-beta-santalol and methoxy-beta-santalol. These two oxygen-containing santalol analogues were synthesized by total syntheses starting from apocamphenilone. A common intermediate for both target molecules, an appropriate bicyclic ketoaldehyde, proved to be inapplicable. Therefore methoxy-beta-santalol was prepared by insertion of an ethyldioxolane sidechain into apocamphenilone and completing the synthesis by five additional steps. Keto-beta-santalol was prepared on a convergent route by insertion of the already prefabricated sidechain into the starting ketone, followed by one additional step. The presence of the second oxygen atom leads to the complete loss of the odour, which is the evidence that apart from the molecular shape, the electrostatic potential has to be taken into account in molecular similarity studies of this class of compounds. (C) Elsevier, Paris.