(Z)-7-Iodo-1,8,8-trimethoxy-oct-1-ene | 221072-22-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-7-Iodo-1,8,8-trimethoxy-oct-1-ene
• CAS: 221072-22-6
• 化学式: C₁₁H₂₁IO₃
• 分子量: 328.19
• InChiKey: FGQBHAFUVDDPQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  15.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-7-Iodo-1,8,8-trimethoxy-oct-1-ene 在 三氟甲磺酸三甲基硅酯 、 二氯乙基铝 、 一氯化碘 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Stereoselective transformation of 1-alkeny ether (R1CH=CHOMe) into alkene (R1CH=CHR2) based on stereospecific elimination of the vicinal iodo(methoxy)alkane

  摘要：

  Treatment of alkenyl methyl ether with ICl rapidly gave 1-chloro-2-iodo-1-methoxyalkane quantitatively. Without isolation, this dihalide was treated with Et3Al to afford anti-iodo(methoxy)alkane in good yield with high stereoselectivity. The stereochemistry of the starting alkenyl ether did not affect the stereochemical outcome of the product. The use of alkynylaluminum ((RC=C)(2)AlEt) resulted in alkynylation of the alpha-chloro-beta-iodoether. Anti-iodo(methoxy)alkane was converted into (Z)-alkene upon treatment with n-BuLi in hexane-ether at -78 degrees C. On the other hand, the reaction of the same anti-iodo(methoxy)alkane with allylsilane-TiCl4 provided (E)-alkene. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01066-7
• 作为产物：
  描述：

  甲醇 、 1,8-dimethoxy-(E,Z)-1,7-octadiene 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以60%的产率得到(Z)-7-Iodo-1,8,8-trimethoxy-oct-1-ene
  参考文献：
  名称：

  Stereoselective transformation of 1-alkeny ether (R1CH=CHOMe) into alkene (R1CH=CHR2) based on stereospecific elimination of the vicinal iodo(methoxy)alkane

  摘要：

  Treatment of alkenyl methyl ether with ICl rapidly gave 1-chloro-2-iodo-1-methoxyalkane quantitatively. Without isolation, this dihalide was treated with Et3Al to afford anti-iodo(methoxy)alkane in good yield with high stereoselectivity. The stereochemistry of the starting alkenyl ether did not affect the stereochemical outcome of the product. The use of alkynylaluminum ((RC=C)(2)AlEt) resulted in alkynylation of the alpha-chloro-beta-iodoether. Anti-iodo(methoxy)alkane was converted into (Z)-alkene upon treatment with n-BuLi in hexane-ether at -78 degrees C. On the other hand, the reaction of the same anti-iodo(methoxy)alkane with allylsilane-TiCl4 provided (E)-alkene. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01066-7