(E)-(1S,2R,3R,4S,5S,6R)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-6-phenylsulfanyl-bicyclo[6.2.1]undec-7-en-3-ol | 200859-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-(1S,2R,3R,4S,5S,6R)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-6-phenylsulfanyl-bicyclo[6.2.1]undec-7-en-3-ol
• CAS: 200859-94-5
• 化学式: C₃₈H₅₂O₇S
• 分子量: 652.893
• InChiKey: QYXVRLFBMMECIB-YMTKOGNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.43
• 重原子数：
  46.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  三氟乙酸酐 、 (E)-(1S,2R,3R,4S,5S,6R)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-6-phenylsulfanyl-bicyclo[6.2.1]undec-7-en-3-ol 生成 Trifluoro-acetic acid (Z)-(1R,4S,5S,6R,7R,8S)-4-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-7-methoxymethoxy-5,11,11-trimethyl-6-(2,2,2-trifluoro-acetoxy)-bicyclo[6.2.1]undec-2-en-1-yl ester
  参考文献：
  名称：

  Application of an S → O Allylic Transposition in the Context of a Bridgehead Olefinic System. New Opportunities for the Structural Modification of Bicyclo[6.2.1]undecanes via Transannular Ring Closure

  摘要：

  A practical route is described for the preparation of allylic sulfide 8, whose double bond resides at a bridgehead site, Following hydride reduction of the ketone carbonyl and sulfoxidation, exposure to trifluoroacetic anhydride results in the operation of an intermolecular S --> O allylic transposition, This central step leads to 14a, an intermediate useful for probing the consequences associated with epoxidation of its cis-cyclononene double bond. A total of three different transannular cyclizations are described in order to demonstrate the ease with which ring closures can operate in a medium-ring setting of this type. Represented are transformations that generate tetrahydrofuran, oxetane, and cyclopropane subunits. The kinetic biases favoring these transformations are highlighted.

  DOI：

  10.1021/jo971591n
• 作为产物：
  描述：

  (1S,2S,3R,4S)-3-(methoxymethoxy)-2-[(Z)-2-[(4S)-4-[(1R)-1-[(4-methoxyphenyl)methoxy]prop-2-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethenyl]-7,7-dimethyl-1-[(Z)-2-phenylsulfanylethenyl]bicyclo[2.2.1]heptan-2-ol 在 lithium aluminium tetrahydride 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 乙醚 为溶剂， 反应 3.25h， 生成 (E)-(1S,2R,3R,4S,5S,6R)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-6-phenylsulfanyl-bicyclo[6.2.1]undec-7-en-3-ol
  参考文献：
  名称：

  Application of an S → O Allylic Transposition in the Context of a Bridgehead Olefinic System. New Opportunities for the Structural Modification of Bicyclo[6.2.1]undecanes via Transannular Ring Closure

  摘要：

  A practical route is described for the preparation of allylic sulfide 8, whose double bond resides at a bridgehead site, Following hydride reduction of the ketone carbonyl and sulfoxidation, exposure to trifluoroacetic anhydride results in the operation of an intermolecular S --> O allylic transposition, This central step leads to 14a, an intermediate useful for probing the consequences associated with epoxidation of its cis-cyclononene double bond. A total of three different transannular cyclizations are described in order to demonstrate the ease with which ring closures can operate in a medium-ring setting of this type. Represented are transformations that generate tetrahydrofuran, oxetane, and cyclopropane subunits. The kinetic biases favoring these transformations are highlighted.

  DOI：

  10.1021/jo971591n