(1S,2R,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane | 682352-10-9

• 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-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane
• 英文别名: (2S)-2-[[(1S,2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6,6-dimethyl-3-bicyclo[3.1.1]heptanyl]sulfanyl]-2-ethoxy-1-phenylethanone
• CAS: 682352-10-9
• 化学式: C₂₆H₄₂O₃SSi
• 分子量: 462.769
• InChiKey: JQPNFSBCIDTIKH-BBUKYQEGSA-N

物化性质

• 沸点：
  504.0±45.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.04
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 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-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 在 N-氯代丁二酰亚胺 、 silver nitrate 、 silver(l) oxide 作用下， 以 四氢呋喃 、 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 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,3S,5R,2'S)-6,6-dimethyl-3-(2'-ethoxy-1'-phenyl-1'-oxo-2'-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-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

• Diastereoselective Preparation of (<i>R</i>)- and (<i>S</i>)-2-Methoxy-2-phenylpent-3-ynoic Acids and Their Use as Reliable Chiral Derivatizing Agents
  作者：Salvador Pérez-Estrada、Pedro Joseph-Nathan、Hugo A. Jiménez-Vázquez、Manuel E. Medina-López、Francisco Ayala-Mata、L. Gerardo Zepeda

  DOI：10.1021/jo2016554

  日期：2012.2.17

  O-acetals 1a and 1b were used as chiral auxiliaries to achieve the diastereoselective preparation of both enantiomers of 2-methoxy-2-phenylpent-3-ynoic acids (MPPAs). The latter were condensed with several chiral secondary alcohols and some primary amines to evaluate their potential as chiral derivatizing agents (CDAs). The 1H NMR spectra of the corresponding esters and amides showed strong consistency with

  苯甲酰基-S，O-乙缩醛1a和1b用作手性助剂，以实现非对映选择性制备2-甲氧基-2-苯基戊-3-炔酸（MPPAs）的两种对映体。后者与几种手性仲醇和一些伯胺缩合，以评估其作为手性衍生剂（CDA）的潜力。的1个对应的酯和酰胺的1 H NMR光谱显示出很强的一致性与甲醇和胺部分，其观察到的ΔδL的绝对构型1和ΔδL 2个值分别为在0.1-0.4和0.02-0.12 ppm的范围。
• 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.