tetramethyl (6Z)-14,17-dioxotricyclo[10.3.3.01,12]octadec-6-ene-13,15,16,18-tetracarboxylate | 141119-98-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tetramethyl (6Z)-14,17-dioxotricyclo[10.3.3.01,12]octadec-6-ene-13,15,16,18-tetracarboxylate
• CAS: 141119-98-4
• 化学式: C₂₆H₃₄O₁₀
• 分子量: 506.55
• InChiKey: BYXGTOLZSAQYLZ-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tetramethyl (6Z)-14,17-dioxotricyclo[10.3.3.01,12]octadec-6-ene-13,15,16,18-tetracarboxylate 在 盐酸 、 四氧化锇 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 叔丁醇 为溶剂， 反应 258.0h， 生成 meso-decahydro-2,2-dimethyl-7a,10a-propano-8H-cyclopenta<7,8>cyclododeca<1,2-d>-1,3-dioxole-9,16(10H)-dione
  参考文献：
  名称：

  Weiss-Cook Condensations Involving Unsaturated and Transannularly Alkylated Cyclododecane-1,2-diones

  摘要：

  (Z)-Cyclododec-7-ene-1,2-dione (4), its alkyne equivalent 7, and the structurally related propellane 14 have been subjected to condensation with dimethyl 1,3-acetonedicarboxylate. The alpha-diketones 4 and 7 undergo the Weiss-Cook condensation normally to deliver diquinane products in high yield. The sterically congested 14 showed no tendency to react. The underlying cause of the parallelism between eight- and twelve-membered rings and the contrasting behavior of cyclodecyl analogs is evaluated in terms of thermodynamic versus kinetic control.

  DOI：

  10.1021/jo00107a013
• 作为产物：
  描述：

  Tetramethyl 14,17-dioxotricyclo[10.3.3.01,12]octadec-6-yne-13,15,16,18-tetracarboxylate 在 Pd-BaSO₄ 喹啉 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 tetramethyl (6Z)-14,17-dioxotricyclo[10.3.3.01,12]octadec-6-ene-13,15,16,18-tetracarboxylate
  参考文献：
  名称：

  Weiss-Cook Condensations Involving Unsaturated and Transannularly Alkylated Cyclododecane-1,2-diones

  摘要：

  (Z)-Cyclododec-7-ene-1,2-dione (4), its alkyne equivalent 7, and the structurally related propellane 14 have been subjected to condensation with dimethyl 1,3-acetonedicarboxylate. The alpha-diketones 4 and 7 undergo the Weiss-Cook condensation normally to deliver diquinane products in high yield. The sterically congested 14 showed no tendency to react. The underlying cause of the parallelism between eight- and twelve-membered rings and the contrasting behavior of cyclodecyl analogs is evaluated in terms of thermodynamic versus kinetic control.

  DOI：

  10.1021/jo00107a013

文献信息

• Abnormal Weiss-Cook condensation of cis-6-cyclodecene-1,2-dione with dimethyl 1,3-acetonedicarboxylate. The consequences of ring strain release
  作者：Leo A. Paquette、Gail E. Underiner、Judith C. Gallucci

  DOI：10.1021/jo00038a054

  日期：1992.6