tert-Butyl 2-(tert-Butylsulfonyl)acetate | 130051-20-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: tert-Butyl 2-(tert-Butylsulfonyl)acetate
• 英文别名: tert-butyl (tert-butylsulfonyl) acetate；tert-butyl 2-tert-butylsulfonylacetate
• CAS: 130051-20-6
• 化学式: C₁₀H₂₀O₄S
• 分子量: 236.332
• InChiKey: INBXUMXGTOQONV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-Butyl 2-(tert-Butylsulfonyl)acetate 在 4-二甲氨基吡啶 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 <1R,1α,3α(E)>-(3-Phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate
  参考文献：
  名称：

  A new way toward Z.alpha.,.beta. unsaturated esters: a pyrethroid application

  摘要：

  Use of the stereospecific condensation of beta-carbalkoxysulfones with aldehydes, followed by the stereospecific reduction of the afforded sulfonyl acrylate with sodium dithionite allows us to propose this method as a new way to prepare Z alpha,beta unsaturated esters. Steric hindrance seems to be the reason for the selectivity of the reduction and the mechanism was proved, by X-ray of an intermediate, to be a cis Michael addition of HSO2-, followed by an anti elimination of SO2 and the sulfinate group. This method discovered in the pyrethroid series for the synthesis of acrinathrin 1 could have general application.

  DOI：

  10.1021/jo00028a034
• 作为产物：
  描述：

  溴乙酸叔丁酯 在 Oxone 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 生成 tert-Butyl 2-(tert-Butylsulfonyl)acetate
  参考文献：
  名称：

  A new way toward Z.alpha.,.beta. unsaturated esters: a pyrethroid application

  摘要：

  Use of the stereospecific condensation of beta-carbalkoxysulfones with aldehydes, followed by the stereospecific reduction of the afforded sulfonyl acrylate with sodium dithionite allows us to propose this method as a new way to prepare Z alpha,beta unsaturated esters. Steric hindrance seems to be the reason for the selectivity of the reduction and the mechanism was proved, by X-ray of an intermediate, to be a cis Michael addition of HSO2-, followed by an anti elimination of SO2 and the sulfinate group. This method discovered in the pyrethroid series for the synthesis of acrinathrin 1 could have general application.

  DOI：

  10.1021/jo00028a034

文献信息

• BABIN, D.;DEMONTE, J. -P;TESSIER, J.
  作者：BABIN, D.、DEMONTE, J. -P、TESSIER, J.

  DOI：——

  日期：——