Me2C(CN)SbMe2 | 872610-97-4

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: Me2C(CN)SbMe2
• 英文别名: 2-methyl-2-dimethylstibanyl-propionitrile；2-Dimethylstibanyl-2-methylpropanenitrile；2-dimethylstibanyl-2-methylpropanenitrile
• CAS: 872610-97-4
• 化学式: C₆H₁₂NSb
• 分子量: 219.918
• InChiKey: LUFZVDNYCSMIJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Me2C(CN)SbMe2 在 苯硫酚 作用下， 反应 8.0h， 生成 异丁腈
  参考文献：
  名称：

  Arylthiols as Highly Chemoselective and Environmentally Benign Radical Reducing Agents

  摘要：

  Arylthiols serve as excellent environmentally benign reducing agents for organotellurium, organostibine, and organobismuthine compounds under radical conditions. Both small molecules and macromolecules possessing these heteroatorn groups are reduced under moderate thermal conditions to give near quantitative yields in most cases. The reduction shows high chemoselectivity with respect to the heteroatorn compounds the reactivity decreases in the order alkylbismuthines, alkylstibines, and alkyltellurides, while simple alkyl iodides could not be reduced. Alkyltellurides are selectively reduced in the presence of alkyl iodides even when an excess amount of arylthiol is used. Furthermore, alkylstibines are also selectively reduced in the presence of alkyltellurides. Moreover, the reduction conditions are compatible with the presence of a variety of polar functional groups in the substrates, products, and solvents, which are not tolerant under ionic and metal-catalyzed conditions. Carbon-carbon bond formation is possible with use of the carbon-centered radicals that are generated. The results clearly reveal the synthetic utility of arylthiols in organic synthesis.

  DOI：

  10.1021/jo801200b
• 作为产物：
  描述：

  二甲基溴化锑 在 lithium isopropylamide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 3.25h， 以35%的产率得到Me2C(CN)SbMe2
  参考文献：
  名称：

  ORGANIC ANTIMONY COMPOUND, PROCESS FOR PRODUCING THE SAME, LIVING RADICAL POLYMERIZATION INITIATOR, PROCESS FOR PRODUCING POLYMER USING THE SAME, AND POLYMER

  摘要：

  公开号：

  EP1767539B1

文献信息

• ORGANIC ANTIMONY COMPOUND, PROCESS FOR PRODUCING THE SAME, LIVING RADICAL POLYMERIZATION INITIATOR, PROCESS FOR PRODUCING POLYMER USING THE SAME, AND POLYMER
  申请人：OTSUKA CHEMICAL COMPANY, LTD.

  公开号：EP1767539B1

  公开（公告）日：2011-07-27
• Arylthiols as Highly Chemoselective and Environmentally Benign Radical Reducing Agents
  作者：Shigeru Yamago、Atsushi Matsumoto

  DOI：10.1021/jo801200b

  日期：2008.9.19

  Arylthiols serve as excellent environmentally benign reducing agents for organotellurium, organostibine, and organobismuthine compounds under radical conditions. Both small molecules and macromolecules possessing these heteroatorn groups are reduced under moderate thermal conditions to give near quantitative yields in most cases. The reduction shows high chemoselectivity with respect to the heteroatorn compounds the reactivity decreases in the order alkylbismuthines, alkylstibines, and alkyltellurides, while simple alkyl iodides could not be reduced. Alkyltellurides are selectively reduced in the presence of alkyl iodides even when an excess amount of arylthiol is used. Furthermore, alkylstibines are also selectively reduced in the presence of alkyltellurides. Moreover, the reduction conditions are compatible with the presence of a variety of polar functional groups in the substrates, products, and solvents, which are not tolerant under ionic and metal-catalyzed conditions. Carbon-carbon bond formation is possible with use of the carbon-centered radicals that are generated. The results clearly reveal the synthetic utility of arylthiols in organic synthesis.