2-(3-iodo-4,5-dihydroselenophen-2-yl)propan-2-ol | 1221975-36-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3-iodo-4,5-dihydroselenophen-2-yl)propan-2-ol
• 英文别名: 2-(4-Iodo-2,3-dihydroselenophen-5-yl)propan-2-ol
• CAS: 1221975-36-5
• 化学式: C₇H₁₁IOSe
• 分子量: 317.028
• InChiKey: YYYQWJDIAJDCBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(3-iodo-4,5-dihydroselenophen-2-yl)propan-2-ol 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以70%的产率得到2-(3-iodoselenophen-2-yl)propan-2-ol
  参考文献：
  名称：

  Synthesis of 2,3-Dihydroselenophene and Selenophene Derivatives by Electrophilic Cyclization of Homopropargyl Selenides

  摘要：

  The synthesis of several highly functionalized 2,3-dihydroselenophenes from homopropargyl selenides via electrophilic cyclization is described. Electrophiles such as 12, ICI, and PhSeBr were used in a simple process employing CH2Cl2 as solvent at room temperature, which gave the cyclized products in high yields. 4-lodo-2,3-dihydroselenophenes obtained by this methodology were submitted to a dehydrogenation reaction using 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to give 3-iodoselenophenes. 4-lodo-5-phenyl-2,3-dihydroselenophene was also submitted to the thiol copper-catalyzed and Heck-type reactions giving the desired products under mild reaction conditions.

  DOI：

  10.1021/ol1003753
• 作为产物：
  描述：

  6-(butylselanyl)-2-methylhex-3-yn-2-ol 在 碘 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到2-(3-iodo-4,5-dihydroselenophen-2-yl)propan-2-ol
  参考文献：
  名称：

  Synthesis of 2,3-Dihydroselenophene and Selenophene Derivatives by Electrophilic Cyclization of Homopropargyl Selenides

  摘要：

  The synthesis of several highly functionalized 2,3-dihydroselenophenes from homopropargyl selenides via electrophilic cyclization is described. Electrophiles such as 12, ICI, and PhSeBr were used in a simple process employing CH2Cl2 as solvent at room temperature, which gave the cyclized products in high yields. 4-lodo-2,3-dihydroselenophenes obtained by this methodology were submitted to a dehydrogenation reaction using 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to give 3-iodoselenophenes. 4-lodo-5-phenyl-2,3-dihydroselenophene was also submitted to the thiol copper-catalyzed and Heck-type reactions giving the desired products under mild reaction conditions.

  DOI：

  10.1021/ol1003753

文献信息

• Synthesis and Reactivity of 3-Alkynyldihydroselenophene Derivatives
  作者：Alisson R. Rosário、Ricardo F. Schumacher、Bibiana M. Gay、Paulo H. Menezes、Gilson Zeni

  DOI：10.1002/ejoc.201000588

  日期：2010.10

  We present herein our results on the synthesis of 3-alkynyl-dihydroselenophenes by palladium-catalyzed Sonogashira cross-coupling of 3-iododihydroselenophenes with different alkynes under mild conditions in good to excellent yields. The developed protocol tolerated a wide range of functional groups in the dihydroselenophenes and alkynes. These 3-alkynyldihydroselenophenes, bearing the chalcogen group

  我们在此展示了我们在温和条件下通过钯催化的 Sonogashira 与不同炔烃的交叉偶联合成 3-炔基-二氢硒酚的结果，产率良好至极好。开发的协议可以容忍二氢硒酚和炔烃中的各种官能团。这些带有硫属元素基团的 3-炔基二氢硒酚在用 I 2 处理时经历了高度选择性的分子内环化，以提供稠合的二氢硒酚 [2,3,b]-硒酚环。此外，通过该方法获得的 3-炔基二氢硒吩还通过使用 DDQ 进行氧化反应，以中等产率得到芳香硒吩。