S-phenyl (+/-)-1,4-dioxa-8-thiaspiro[4.5]decane-6-carbothioate | 768368-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-phenyl (+/-)-1,4-dioxa-8-thiaspiro[4.5]decane-6-carbothioate
• 英文别名: S-phenyl 1,4-dioxa-8-thiaspiro[4.5]decane-6-carbothioate
• CAS: 768368-63-4
• 化学式: C₁₄H₁₆O₃S₂
• 分子量: 296.411
• InChiKey: YLUQQRVQVRDZRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  S-phenyl (+/-)-1,4-dioxa-8-thiaspiro[4.5]decane-6-carbothioate 在 lithium aluminium tetrahydride 、 水 、 甲基锂 、 仲丁基锂 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.59h， 生成 (+/-)-(3S)-3-[(R)-(6S)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(hydroxy)methyl]tetrahydro-4H-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 、 草酰氯 作用下， 以 甲醇 、 苯 为溶剂， 反应 4.75h， 生成 S-phenyl (+/-)-1,4-dioxa-8-thiaspiro[4.5]decane-6-carbothioate
  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

文献信息

• The thiopyran route to polypropionates. Asymmetric synthesis of the building blocks by enantioselective protonation
  作者：Dale E. Ward、Olukayode T. Akinnusi、Idralyn Q. Alarcon、Vishal Jheengut、Jianheng Shen、J. Wilson Quail

  DOI：10.1016/j.tetasy.2004.06.027

  日期：2004.8

  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.