(1R,1α,3α)-6,6-Dimethyl-4-<2-tert-butoxy-2-oxo-1-(tert-butylsulfonyl)ethyl>-3-oxabicyclo<3.1.0>hexan-2-one | 130051-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,1α,3α)-6,6-Dimethyl-4-<2-tert-butoxy-2-oxo-1-(tert-butylsulfonyl)ethyl>-3-oxabicyclo<3.1.0>hexan-2-one
• 英文别名: tert-butyl 2-tert-butylsulfonyl-2-[(1S,5R)-6,6-dimethyl-4-oxo-3-oxabicyclo[3.1.0]hexan-2-yl]acetate
• CAS: 130051-19-3
• 化学式: C₁₇H₂₈O₆S
• 分子量: 360.472
• InChiKey: BTLIAWKVWOCCJL-QKEWWQLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  86.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R,1α,3α)-6,6-Dimethyl-4-<2-tert-butoxy-2-oxo-1-(tert-butylsulfonyl)ethyl>-3-oxabicyclo<3.1.0>hexan-2-one 在 4-二甲氨基吡啶 、 sodium dithionite 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 (1R,3S)-3-[(1R,2R)-2-tert-Butoxycarbonyl-1-((R)-methoxysulfinyl)-2-(2-methyl-propane-2-sulfonyl)-ethyl]-2,2-dimethyl-cyclopropanecarboxylic acid 3-phenoxy-benzyl ester
  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 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 生成 (1R,1α,3α)-6,6-Dimethyl-4-<2-tert-butoxy-2-oxo-1-(tert-butylsulfonyl)ethyl>-3-oxabicyclo<3.1.0>hexan-2-one
  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：——