(1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-hydroxymethyl-bicyclo[3.1.1]heptane | 682352-08-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-hydroxymethyl-bicyclo[3.1.1]heptane
• 英文别名: (2S)-2-ethoxy-2-[[(1S,2R,3S,5R)-2-(hydroxymethyl)-6,6-dimethyl-3-bicyclo[3.1.1]heptanyl]sulfanyl]-1-phenylethanone
• CAS: 682352-08-5
• 化学式: C₂₀H₂₈O₃S
• 分子量: 348.507
• InChiKey: SSWUMGKDIQNSGR-QSUVVDIXSA-N

物化性质

• 沸点：
  476.8±40.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-hydroxymethyl-bicyclo[3.1.1]heptane 在 4-二甲氨基吡啶 、 N-氯代丁二酰亚胺 、 silver nitrate 、 三乙胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.25h， 生成 (R)-2-羟基-2-苯基丁酸
  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 N-氯代丁二酰亚胺 、 lithium aluminium tetrahydride 、 对甲苯磺酸 、 silver nitrate 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,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-hydroxymethyl-bicyclo[3.1.1]heptane
  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

• New S,O-acetals from (1R)-(−)-myrtenal as chiral auxiliaries in nucleophilic additions
  作者：Luis Chacón-Garcı́a、Selene Lagunas-Rivera、Salvador Pérez-Estrada、M. Elena Vargas-Dı́az、Pedro Joseph-Nathan、Joaquı́n Tamariz、L.Gerardo Zepeda

  DOI：10.1016/j.tetlet.2004.01.046

  日期：2004.3

  Treatment of hydroxythiol 4 with alpha,alpha-diethoxyacetophenone at room temperature yielded a mixture of epimeric S,O-acetals 6 and 7 (1:4. 92%, yield), which were efficiently separated by flash chromatography. The OTBS derivatives 8 and 9 were treated with several Grignard reagents to afford carbinols 10 and 13 respectively (85-99%, yield, >95% dr). After successive hydrolysis and reduction of 10 and 13 it is possible to obtain either enantiomer of diols 16 in high optical purity (>95% er). (C) 2004 Elsevier 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.