(S)-5,5-dimethyl-7-(prop-1-en-2-yl)-4,6-dioxaspiro[2.5]octane | 1609178-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-5,5-dimethyl-7-(prop-1-en-2-yl)-4,6-dioxaspiro[2.5]octane
• 英文别名: (7S)-5,5-dimethyl-7-prop-1-en-2-yl-4,6-dioxaspiro[2.5]octane
• CAS: 1609178-39-3
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: CGWNHVDQINBGAG-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (S)-5,5-dimethyl-7-(prop-1-en-2-yl)-4,6-dioxaspiro[2.5]octane 在 9-硼双环[3.3.1]壬烷 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 6.0h， 以75%的产率得到
  参考文献：
  名称：

  A cyclopropanol-based approach to synthesis of Unit A of the cryptophycins

  摘要：

  A new asymmetric synthesis of Unit A of the cryptophycins has been carried out yielding 13% of the target product over 14 steps. The key steps of the synthesis were diastereoselective hydroboration-oxidation reactions performed on the alkenyl moiety of a 1,3-dioxane derivative 8, which can be easily prepared via the Kulinkovich cyclopropanation of protected diethyl (S)-(-)-malate followed by transformation of the resulting small rings of the product 6 into the functional groups necessary for the synthesis of the target compound. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.03.011
• 作为产物：
  描述：

  (7S)-7-(3-bromoprop-1-en-2-yl)-5,5-dimethyl-4,6-dioxaspiro[2.5]octane 在 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以91%的产率得到(S)-5,5-dimethyl-7-(prop-1-en-2-yl)-4,6-dioxaspiro[2.5]octane
  参考文献：
  名称：

  A cyclopropanol-based approach to synthesis of Unit A of the cryptophycins

  摘要：

  A new asymmetric synthesis of Unit A of the cryptophycins has been carried out yielding 13% of the target product over 14 steps. The key steps of the synthesis were diastereoselective hydroboration-oxidation reactions performed on the alkenyl moiety of a 1,3-dioxane derivative 8, which can be easily prepared via the Kulinkovich cyclopropanation of protected diethyl (S)-(-)-malate followed by transformation of the resulting small rings of the product 6 into the functional groups necessary for the synthesis of the target compound. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.03.011