(7S)-7-(3-bromoprop-1-en-2-yl)-5,5-dimethyl-4,6-dioxaspiro[2.5]octane | 868158-77-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (7S)-7-(3-bromoprop-1-en-2-yl)-5,5-dimethyl-4,6-dioxaspiro[2.5]octane
• CAS: 868158-77-4
• 化学式: C₁₁H₁₇BrO₂
• 分子量: 261.159
• InChiKey: QYBMZEJLYSBUTF-VIFPVBQESA-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：
  2
• 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：

  (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

文献信息

• New synthesis of syn-stereodiad building block for polyketides. Formal synthesis of arenamides A and C
  作者：D. G. Shklyaruck

  DOI：10.1134/s107042801504020x

  日期：2015.4

  6-dioxaspiro[2.5]octane [available from diethyl (S)-malate] into methyl 2-[(4S)-2,2-dimethyl-5-methylidene-1,3-dioxan-4-yl]acetate, and conditions for diastereoselective reduction of the double C=C bond in the latter have been optimized. The reduction product has been converted into (3S,4S)-3-[tert-butyl(dimethyl)siloxy]-4-methyldecanoic acid which is a building block for the synthesis of arenamides

  已经开发了一种有效的方法来转化（7 S）-7-（3-溴丙-1-烯-2-基）-5,5-二甲基-4,6-二氧杂螺[2.5]辛烷[可从二乙基中获得（S）-苹果酸]成2-[（（4 S）-2,2-二甲基-5-亚甲基-1,3-二氧六环-4-基]乙酸甲酯]和非对映选择性还原双C = C键的条件在后者中已进行了优化。还原产物已转化为（3 S，4 S）-3- [叔丁基（二甲基）甲硅烷氧基] -4-甲基癸酸，这是合成芳酰胺A和C的基础材料，具有明显的抗肿瘤作用的天然化合物活性并有效抑制二氧化氮和前列腺素E 2（PGE2）。
• A cyclopropanol-based approach to synthesis of Unit A of the cryptophycins
  作者：Denis G. Shklyaruck

  DOI：10.1016/j.tetasy.2014.03.011

  日期：2014.4

  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.