(1S,2R,6S)-9,9-dimethyl-4-oxa-5-thiatricyclo[6.1.1.0^2,6]decane 5-oxide | 476431-61-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2R,6S)-9,9-dimethyl-4-oxa-5-thiatricyclo[6.1.1.0^2,6]decane 5-oxide
• 英文别名: (1S,2R,6S,8R)-9,9-dimethyl-4-oxa-5lambda4-thiatricyclo[6.1.1.02,6]decane 5-oxide；(1S,2R,6S,8R)-9,9-dimethyl-4-oxa-5λ4-thiatricyclo[6.1.1.02,6]decane 5-oxide
• CAS: 476431-61-5
• 化学式: C₁₀H₁₆O₂S
• 分子量: 200.302
• InChiKey: MKWKHAVVUPFQRS-IVNHHRSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R,6S)-9,9-dimethyl-4-oxa-5-thiatricyclo[6.1.1.0^2,6]decane 5-oxide 在 lithium aluminium tetrahydride 作用下， 以72%的产率得到10-hydroxyisopinocampheylthiol
  参考文献：
  名称：

  Enantioselective synthesis of either enantiomer of α-alkyl-α-hydroxy-α-phenylacetic acids using chiral auxiliaries

  摘要：

  The enantioselective synthesis of either enantiomer of of alpha-alkyl-alpha-hydroxy-alpha-phenylacetic acids was achieved by using 2-acyloxathianes 1a-c and the mixed acyl-S,O-acetals 7 and 8 as chiral auxiliaries, which can straightforwardly be prepared from (1R)-(-)-myrtenal. This procedure allowed the preparation of the title compounds in >95% enantiomeric excess (ee). (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.03.032
• 作为产物：
  描述：

  10-hydroxyisopinocampheylthiol 在 4-二甲氨基吡啶 、 N-氯代丁二酰亚胺 、 lithium aluminium tetrahydride 、 对甲苯磺酸 、 silver nitrate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 、 苯 为溶剂， 反应 30.5h， 生成 (1S,2R,6S)-9,9-dimethyl-4-oxa-5-thiatricyclo[6.1.1.0^2,6]decane 5-oxide
  参考文献：
  名称：

  Enantioselective synthesis of either enantiomer of α-alkyl-α-hydroxy-α-phenylacetic acids using chiral auxiliaries

  摘要：

  The enantioselective synthesis of either enantiomer of of alpha-alkyl-alpha-hydroxy-alpha-phenylacetic acids was achieved by using 2-acyloxathianes 1a-c and the mixed acyl-S,O-acetals 7 and 8 as chiral auxiliaries, which can straightforwardly be prepared from (1R)-(-)-myrtenal. This procedure allowed the preparation of the title compounds in >95% enantiomeric excess (ee). (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.03.032

文献信息

• Highly diastereoselective nucleophilic additions using a novel myrtenal-derived oxathiane as a chiral auxiliary
  作者：Federico Martı́nez-Ramos、Marı́a Elena Vargas-Dı́az、Luis Chacón-Garcı́a、Joaquı́n Tamariz、Pedro Joseph-Nathan、L.Gerardo Zepeda

  DOI：10.1016/s0957-4166(01)00545-6

  日期：2001.12

  The synthesis of novel oxathiane 3 and its acetyl derivative 12, from commercially available (-)myrtenal 4, is described. The addition of several nucleophilic reagents to 12 furnished the corresponding tertiary carbinols in highly diastereomeric excess. The hydrolysis of 11a, b yielded the expected alpha-hydroxycarbonyl compounds in excellent enantiomeric excess. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Enantioselective synthesis of either enantiomer of α-alkyl-α-hydroxy-α-phenylacetic acids using chiral auxiliaries
  作者：Salvador Pérez-Estrada、Selene Lagunas-Rivera、Marı́a Elena Vargas-Dı́az、Pedro Velázquez-Ponce、Pedro Joseph-Nathan、L. Gerardo Zepeda

  DOI：10.1016/j.tetasy.2005.03.032

  日期：2005.5

  The enantioselective synthesis of either enantiomer of of alpha-alkyl-alpha-hydroxy-alpha-phenylacetic acids was achieved by using 2-acyloxathianes 1a-c and the mixed acyl-S,O-acetals 7 and 8 as chiral auxiliaries, which can straightforwardly be prepared from (1R)-(-)-myrtenal. This procedure allowed the preparation of the title compounds in >95% enantiomeric excess (ee). (C) 2005 Published by Elsevier Ltd.