(R)-1,4-dioxa-8-thiaspiro[4.5]decane-6-carboxylic acid | 768368-58-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1,4-dioxa-8-thiaspiro[4.5]decane-6-carboxylic acid
• 英文别名: (6R)-1,4-dioxa-8-thiaspiro[4.5]decane-6-carboxylic acid
• CAS: 768368-58-7
• 化学式: C₈H₁₂O₄S
• 分子量: 204.247
• InChiKey: OCBDUACINCGEHB-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.57
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-1,4-dioxa-8-thiaspiro[4.5]decane-6-carboxylic acid 在 lithium aluminium tetrahydride 、 水 、 戴斯-马丁氧化剂 、 magnesium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.92h， 生成 (S)-3-((S)-(S)-1,4-Dioxa-8-thia-spiro[4.5]dec-6-yl-hydroxy-methyl)-tetrahydro-thiopyran-4-one
  参考文献：
  名称：

  The thiopyran route to polypropionates. Asymmetric synthesis of the building blocks by enantioselective protonation

  摘要：

  Enantioselective protonation of the s-BuLi derived lithium enolate of (S)-phenyl 1,4-dioxa-8-thia-spiro[4.5]decane-6-carbothioate 14 with N-isopropylephedrine 15 gives 14 as a 10:1 mixture of enantiomers. Recrystallization of nonracemic 14 gives a highly enantioenriched material (>90% ee), which can be converted into 1,4-dioxa-8-thia-spiro[4.5]decane-6-carboxaldehyde 2 without racemization. Diastereoselective aldol reactions of tetrahydro-4H-thiopyran-4-one with nonracemic 2 proceed with negligible racemization to give adducts that are useful building blocks for polypropionate synthesis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.027
• 作为产物：
  描述：

  methyl 1,4-dioxa-8-thiaspiro[4.5]decane-6-carboxylate 在 sodium hydroxide 、 (S)-(-)- α-甲基苄胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.5h， 生成 (R)-1,4-dioxa-8-thiaspiro[4.5]decane-6-carboxylic acid
  参考文献：
  名称：

  The thiopyran route to polypropionates. Asymmetric synthesis of the building blocks by enantioselective protonation

  摘要：

  Enantioselective protonation of the s-BuLi derived lithium enolate of (S)-phenyl 1,4-dioxa-8-thia-spiro[4.5]decane-6-carbothioate 14 with N-isopropylephedrine 15 gives 14 as a 10:1 mixture of enantiomers. Recrystallization of nonracemic 14 gives a highly enantioenriched material (>90% ee), which can be converted into 1,4-dioxa-8-thia-spiro[4.5]decane-6-carboxaldehyde 2 without racemization. Diastereoselective aldol reactions of tetrahydro-4H-thiopyran-4-one with nonracemic 2 proceed with negligible racemization to give adducts that are useful building blocks for polypropionate synthesis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.027