1-iodo-2-(3,4-methylenedioxyphenyl)acetylene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-iodo-2-(3,4-methylenedioxyphenyl)acetylene
• 英文别名: 5-(2-Iodoethynyl)-1,3-benzodioxole；5-(2-iodoethynyl)-1,3-benzodioxole
• 化学式: C₉H₅IO₂
• 分子量: 272.042
• InChiKey: JNTVTHBBFKDFAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  胡椒醇 在 四溴化碳 、 sodium hexamethyldisilazane 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 21.0h， 生成 1-iodo-2-(3,4-methylenedioxyphenyl)acetylene
  参考文献：
  名称：

  One-Pot Synthesis of 1-Iodoalkynes and Trisubstituted Alkenes from Benzylic and Allylic Bromides

  摘要：

  1-Iodoalkynes are formed in moderate to high yields from readily accessible benzylic and allylic alkyl bromides by a one-pot homologation/double elimination procedure with iodoform (CHI3). The developed conditions include facile purification and avoid the use of an excess of triphenylphosphine (PPh3), as described in classical Corey-Fuchs iodoalkynylation conditions. Replacing CHI3 with CHI2CI allows the isolation of the corresponding gem-(2)-chloro-(E)-iodoalkene in good yield and stereoselectivity. Moreover, the use of benzhydryl bromides as nucleophiles enables the synthesis of trisubstituted alkenes under similar reaction conditions.

  DOI：

  10.1021/ol302544s

文献信息

• Catalytic Hunsdiecker Reaction of α,β-Unsaturated Carboxylic Acids:  How Efficient Is the Catalyst?
  作者：Jaya Prakash Das、Sujit Roy

  DOI：10.1021/jo025868h

  日期：2002.11.1

  UV-vis spectrophotometry is utilized to measure the relative efficiency of lithium acetate, tetrabutylammonium. trifluoroacetate, and triethylamine as catalysts for the conversion of 4-methoxycinnamic acid to 4-methoxy-beta-bromostyrene. In acetonitrile-water as solvent, the efficiency order is lithium acetate > triethylamine > tetrabutylammonium trifluoroacetate. For triethylamine as catalyst, solvent-dependent order is acetonitrile-water > dichloromethane > acetonitrile. Using triethylamine as catalyst (5-20 mol %), cinnamic acids, and propiolic acids are converted to corresponding beta-bromostyrenes and 1-halo-1-alkynes in 60-98% isolated yields within 1-5 min.
• One-Pot Synthesis of 1-Iodoalkynes and Trisubstituted Alkenes from Benzylic and Allylic Bromides
  作者：Guillaume Pelletier、Sharon Lie、James J. Mousseau、André B. Charette

  DOI：10.1021/ol302544s

  日期：2012.11.2

  1-Iodoalkynes are formed in moderate to high yields from readily accessible benzylic and allylic alkyl bromides by a one-pot homologation/double elimination procedure with iodoform (CHI3). The developed conditions include facile purification and avoid the use of an excess of triphenylphosphine (PPh3), as described in classical Corey-Fuchs iodoalkynylation conditions. Replacing CHI3 with CHI2CI allows the isolation of the corresponding gem-(2)-chloro-(E)-iodoalkene in good yield and stereoselectivity. Moreover, the use of benzhydryl bromides as nucleophiles enables the synthesis of trisubstituted alkenes under similar reaction conditions.