meso-decahydro-2,2-dimethyl-7a,10a-propano-8H-cyclopenta<7,8>cyclododeca<1,2-d>-1,3-dioxole-9,16(10H)-dione | 162251-46-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: meso-decahydro-2,2-dimethyl-7a,10a-propano-8H-cyclopenta<7,8>cyclododeca<1,2-d>-1,3-dioxole-9,16(10H)-dione
• 英文别名: (6R,10S)-8,8-dimethyl-7,9-dioxatetracyclo[13.3.3.01,15.06,10]henicosane-17,20-dione
• CAS: 162251-46-9
• 化学式: C₂₁H₃₂O₄
• 分子量: 348.483
• InChiKey: YUHKTNPBYNZTCG-FWGXRIOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  meso-decahydro-2,2-dimethyl-7a,10a-propano-8H-cyclopenta<7,8>cyclododeca<1,2-d>-1,3-dioxole-9,16(10H)-dione 在 lithium aluminium tetrahydride 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 生成 cis-4,5,6,7,8,9,10,11,12,13-decahydro-3a,13a-propeno-1H-cyclopentacyclodecene-8,9-diol
  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 (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

文献信息

• Weiss-Cook Condensations Involving Unsaturated and Transannularly Alkylated Cyclododecane-1,2-diones
  作者：Heiner Detert、James C. Lanter、Leo A. Paquette

  DOI：10.1021/jo00107a013

  日期：1995.1

  (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.