2-Bromo-1-butyl-2-(toluene-4-sulfinyl)-spiro[2.14]heptadecane-1-carbonitrile | 882696-39-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Bromo-1-butyl-2-(toluene-4-sulfinyl)-spiro[2.14]heptadecane-1-carbonitrile
• 英文别名: 2-Bromo-1-butyl-2-(4-methylphenyl)sulfinylspiro[2.14]heptadecane-1-carbonitrile；2-bromo-1-butyl-2-(4-methylphenyl)sulfinylspiro[2.14]heptadecane-1-carbonitrile
• CAS: 882696-39-1
• 化学式: C₂₉H₄₄BrNOS
• 分子量: 534.644
• InChiKey: JIIROAZWZZMJEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  60.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Bromo-1-butyl-2-(toluene-4-sulfinyl)-spiro[2.14]heptadecane-1-carbonitrile 在 异丁腈 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到2-Cyclopentadecylidenemethylene-hexanenitrile
  参考文献：
  名称：

  A novel route to fully substituted cyanoallenes from three components, ketones, chloromethyl p-tolyl sulfoxide, and nitriles, via α-bromocyclopropyl p-tolyl sulfoxides

  摘要：

  Treatment of 1-chlorovinyl p-tolyl sulfoxides. which were derived front ketones and chloromethyl p-tolyl sulfoxide in high yields, with lithium alpha-carbanion of nitriles gave the adducts in quantitative yields. The adducts were converted to alpha-bromocyclopropyl p-tolyl sulfoxides in two steps in good yields. Finally, the sulfoxides were treated with excess lithium carbanion of isobutyronitrile to afford fully Substituted cyanoallenes in high to quantitative yields via sulfoxide-lithium exchange reaction. This procedure offers a novel synthetic method for fully substituted cyanoallenes with coupling of three components (ketones, chloromethyl p-tolyl sulfoxide, and nitriles) in good overall yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.01.161
• 作为产物：
  描述：

  在 四溴化碳 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 2-Bromo-1-butyl-2-(toluene-4-sulfinyl)-spiro[2.14]heptadecane-1-carbonitrile
  参考文献：
  名称：

  A novel route to fully substituted cyanoallenes from three components, ketones, chloromethyl p-tolyl sulfoxide, and nitriles, via α-bromocyclopropyl p-tolyl sulfoxides

  摘要：

  Treatment of 1-chlorovinyl p-tolyl sulfoxides. which were derived front ketones and chloromethyl p-tolyl sulfoxide in high yields, with lithium alpha-carbanion of nitriles gave the adducts in quantitative yields. The adducts were converted to alpha-bromocyclopropyl p-tolyl sulfoxides in two steps in good yields. Finally, the sulfoxides were treated with excess lithium carbanion of isobutyronitrile to afford fully Substituted cyanoallenes in high to quantitative yields via sulfoxide-lithium exchange reaction. This procedure offers a novel synthetic method for fully substituted cyanoallenes with coupling of three components (ketones, chloromethyl p-tolyl sulfoxide, and nitriles) in good overall yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.01.161

文献信息

• The first example of 2,2-dilithiocyanocyclopropanes: generation from 2-bromo-2-sulfinylcyanocyclopropanes with tert-butyllithium, property, and a synthesis of fully substituted cyanocyclopropanes
  作者：Iori Fukushima、Youhei Gouda、Tsuyoshi Satoh

  DOI：10.1016/j.tetlet.2006.12.148

  日期：2007.3

  through concomitant sulfoxide–lithium and bromine–lithium exchange reactions. The gem-dianions were found to be stable at −78 °C for at least 30 min. Reaction of the gem-dianions with electrophiles gave fully substituted cyanocyclopropanes in moderate yields.

  通过-亚砜-锂和溴-锂的交换反应，在-78°C下，2-溴-2-（对甲苯磺酰基）氰基环丙烷与叔丁基锂在甲苯中很容易生成2，2-二硫代氰基环丙烷。所述宝石-dianions被发现在-78℃是稳定至少30分钟。宝石-阴离子与亲电试剂的反应以中等收率得到了完全取代的氰基环丙烷。