(Z)-(1S,2R,4S,5S,8R)-2,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one | 200860-11-3

• 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: (Z)-(1S,2R,4S,5S,8R)-2,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one
• 英文别名: (1S,2R,4S,5S,6Z,8R)-2,8-dihydroxy-5-[(4S)-4-[(1R)-1-[(4-methoxyphenyl)methoxy]prop-2-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4,11,11-trimethylbicyclo[6.2.1]undec-6-en-3-one
• CAS: 200860-11-3
• 化学式: C₃₀H₄₂O₇
• 分子量: 514.659
• InChiKey: CAGHKDROIIZUMR-DRZMJQEMSA-N

物化性质

• 沸点：
  629.169±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.146±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z)-(1S,2R,4S,5S,8R)-2,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以77%的产率得到(1S,2S,4S,5R,6S,8R,9S)-1,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-6,12,12-trimethyl-3-oxa-tricyclo[7.2.1.0^2,4]dodecan-7-one
  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：

  (Z)-(1S,2R,4S,5S,8R)-8-Hydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one 在 4-甲基苯磺酸吡啶 作用下， 以 叔丁醇 为溶剂， 反应 48.0h， 以70%的产率得到(Z)-(1S,2R,4S,5S,8R)-2,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one
  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