(Z)-1-methoxy-2-(iodomethylidene)-4-pentene | 145278-29-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (Z)-1-methoxy-2-(iodomethylidene)-4-pentene
• 英文别名: (1Z)-1-iodo-2-(methoxymethyl)penta-1,4-diene
• CAS: 145278-29-1
• 化学式: C₇H₁₁IO
• 分子量: 238.068
• InChiKey: BDQWCEDJCWTYTC-ALCCZGGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 (Z)-1-methoxy-2-(iodomethylidene)-4-pentene 在 叔丁基锂 作用下， 生成 (Z)-1-methoxy-2-<(trimethylsilyl)methylidene>-4-pentene
  参考文献：
  名称：

  Reactivity of allylic dimetallic zinc reagents. 1

  摘要：

  Allylic 1,1-dimetallic species 2, prepared in situ from the propargylic ether 1, are multicoupling reagents. They were allowed to react in a one-pot maction, with a large variety of electrophiles E1-carbonyl compounds (acyl chlorides, aldehydes, ketones, phenyl isocyanate, methyl chloroformate), alkyl bromides, and an amino ether-and then E2-acidic water, iodine, aryl or vinyl iodide in the presence of palladium(0). The isolated yields, based on 1 (5 steps), are fair to good in most cases. The first attack (E1) always occurs on the carbon atom alpha to the oxygen; the second attack (E2) is regio- and stereoselective on the carbon atom a to the TMS moiety.

  DOI：

  10.1021/jo00051a042
• 作为产物：
  描述：

  (Z)-2-(iodomethylidene)-4-penten-1-ol 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以80%的产率得到(Z)-1-methoxy-2-(iodomethylidene)-4-pentene
  参考文献：
  名称：

  Reactivity of allylic dimetallic zinc reagents. 1

  摘要：

  Allylic 1,1-dimetallic species 2, prepared in situ from the propargylic ether 1, are multicoupling reagents. They were allowed to react in a one-pot maction, with a large variety of electrophiles E1-carbonyl compounds (acyl chlorides, aldehydes, ketones, phenyl isocyanate, methyl chloroformate), alkyl bromides, and an amino ether-and then E2-acidic water, iodine, aryl or vinyl iodide in the presence of palladium(0). The isolated yields, based on 1 (5 steps), are fair to good in most cases. The first attack (E1) always occurs on the carbon atom alpha to the oxygen; the second attack (E2) is regio- and stereoselective on the carbon atom a to the TMS moiety.

  DOI：

  10.1021/jo00051a042

文献信息

• MIXAJLOV, B. M.;LAVRINOVICH, L. I., IZV. AN CCCP. CEP. XIM., 1983, N 12, 2836-2837
  作者：MIXAJLOV, B. M.、LAVRINOVICH, L. I.

  DOI：——

  日期：——