(2Z)-3-(3,4,4a,5,6,7-hexahydro-4a,8-dimethyl-2-naphthalenyl)-3-methyl-2-propenal | 123523-83-1

• 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: (2Z)-3-(3,4,4a,5,6,7-hexahydro-4a,8-dimethyl-2-naphthalenyl)-3-methyl-2-propenal
• 英文别名: rac-(Z)-3-(4a,8-dimethyl-3,4,4a,5,6,7-hexahydronaphthalen-2-yl)but-2-enal；(Z)-3-(4a,8-dimethyl-4,5,6,7-tetrahydro-3H-naphthalen-2-yl)but-2-enal
• CAS: 123523-83-1
• 化学式: C₁₆H₂₂O
• 分子量: 230.35
• InChiKey: WYJJZYLDWUPFDY-GHXNOFRVSA-N

物化性质

• 沸点：
  370.1±11.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2Z)-3-(3,4,4a,5,6,7-hexahydro-4a,8-dimethyl-2-naphthalenyl)-3-methyl-2-propenal 在 碘 作用下， 以 正己烷 为溶剂， 反应 4.0h， 生成 (2E)-3-(3,4,4a,5,6,7-hexahydro-4a,8-dimethyl-2-naphthalenyl)-3-methyl-2-propenal
  参考文献：
  名称：

  Stereocontrolled Synthesis of 6-s-cis- and 6-s-trans-Locked 9Z-Retinoids by Hydroxyl-Accelerated Stille Coupling of (Z)-Tri-n-Butylstannylbut-2-en-1-ol and Bicyclic Dienyl Triflates

  摘要：

  Analogues of 9-cis-retinoic acid with locked 6-s-cis and 6-s-trans conformations have been stereoselectively synthesized using a Stille coupling reaction between bicyclic dienyl triflates (5 and 6, respectively) and (Z)-tributylstannylbut-2-en-1-ol (7) to stablish the Z geometry of the polyenic side chain. The mild conditions (25 degrees C, 30 min) of this coupling stand in contrast to the reluctance of the isomeric (E)-tributylstannylbut-2-en-1-ol (18) to react with triflates 5/6. The significant rate differences experimentally observed in Stille reactions between isomeric (Z)- and (E)-tri-n-butylstannylalkenols in favor of the former isomer, even with highly hindered alkenyl triflates, is ascribed to internal coordination of palladium to the heteroatom in the presumably rate-limiting transmetalation step. Dienals and trienals with an E geometry, which are not efficiently available by direct coupling of the corresponding triflates and E-stannanes, can in turn be obtained by isomerization of their Z-isomers.

  DOI：

  10.1021/jo9917588
• 作为产物：
  描述：

  4,4a,5,6,7,8-六氢-4a,8-二甲基萘-2(3H)-酮 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 2,6-二叔丁基-4-甲基吡啶 、 三苯胂 、 戴斯-马丁氧化剂 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 13.58h， 生成 (2Z)-3-(3,4,4a,5,6,7-hexahydro-4a,8-dimethyl-2-naphthalenyl)-3-methyl-2-propenal
  参考文献：
  名称：

  Stereocontrolled Synthesis of 6-s-cis- and 6-s-trans-Locked 9Z-Retinoids by Hydroxyl-Accelerated Stille Coupling of (Z)-Tri-n-Butylstannylbut-2-en-1-ol and Bicyclic Dienyl Triflates

  摘要：

  Analogues of 9-cis-retinoic acid with locked 6-s-cis and 6-s-trans conformations have been stereoselectively synthesized using a Stille coupling reaction between bicyclic dienyl triflates (5 and 6, respectively) and (Z)-tributylstannylbut-2-en-1-ol (7) to stablish the Z geometry of the polyenic side chain. The mild conditions (25 degrees C, 30 min) of this coupling stand in contrast to the reluctance of the isomeric (E)-tributylstannylbut-2-en-1-ol (18) to react with triflates 5/6. The significant rate differences experimentally observed in Stille reactions between isomeric (Z)- and (E)-tri-n-butylstannylalkenols in favor of the former isomer, even with highly hindered alkenyl triflates, is ascribed to internal coordination of palladium to the heteroatom in the presumably rate-limiting transmetalation step. Dienals and trienals with an E geometry, which are not efficiently available by direct coupling of the corresponding triflates and E-stannanes, can in turn be obtained by isomerization of their Z-isomers.

  DOI：

  10.1021/jo9917588

文献信息

• Steen, R. van der; Biesheuvel, P. L.; Erkelens, C., Recueil des Travaux Chimiques des Pays-Bas, 1989, vol. 108, # 3, p. 83 - 93
  作者：Steen, R. van der、Biesheuvel, P. L.、Erkelens, C.、Mathies, R. A.、Lugtenburg, J.

  DOI：——

  日期：——