[(2S,3S,4R)-5-iodo-2,4-dimethyl-3-(2-methylprop-1-enoxy)pentoxy]methylbenzene | 683278-53-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2S,3S,4R)-5-iodo-2,4-dimethyl-3-(2-methylprop-1-enoxy)pentoxy]methylbenzene
• CAS: 683278-53-7
• 化学式: C₁₈H₂₇IO₂
• 分子量: 402.316
• InChiKey: OIZATFFYGOXRPK-XYJFISCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4R)-5-iodo-2,4-dimethyl-3-(2-methylprop-1-enoxy)pentoxy]methylbenzene 在 三乙基硼 、 三(三甲基硅基)硅烷 、 氧气 作用下， 以 苯 为溶剂， 以47%的产率得到(2R,3S,5S)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-5-isopropyl-3-methyl-tetrahydro-furan
  参考文献：
  名称：

  Stereoselection at the Steady State in Radical Cyclizations of Acyclic Systems Containing One Radical Acceptor and Two Precursors in a 1,5- Relationship under Pseudo-First-Order Conditions

  摘要：

  The first example of a successive kinetic resolution of acyclic diastereomeric radical intermediates in a 1,5-relationship under pseudo-first-order conditions is reported. A mechanistic model involves nonselective generation of the radical intermediates followed by different partitioning of these between two different chemical pathways. The "2,5-cis" selectivity in the radical cyclization step arises from transition geometries with the substituents aligned in pseudoequatorial positions.

  DOI：

  10.1021/jo035310p
• 作为产物：
  描述：

  (2S,3S,4S)-3,5-isopropylidenedioxy-2,4-dimethyl-1-pentanol 在 吡啶 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 对甲苯磺酸 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 114.0h， 生成 [(2S,3S,4R)-5-iodo-2,4-dimethyl-3-(2-methylprop-1-enoxy)pentoxy]methylbenzene
  参考文献：
  名称：

  Stereoselection at the Steady State in Radical Cyclizations of Acyclic Systems Containing One Radical Acceptor and Two Precursors in a 1,5- Relationship under Pseudo-First-Order Conditions

  摘要：

  The first example of a successive kinetic resolution of acyclic diastereomeric radical intermediates in a 1,5-relationship under pseudo-first-order conditions is reported. A mechanistic model involves nonselective generation of the radical intermediates followed by different partitioning of these between two different chemical pathways. The "2,5-cis" selectivity in the radical cyclization step arises from transition geometries with the substituents aligned in pseudoequatorial positions.

  DOI：

  10.1021/jo035310p