4-(甲硫代)丁酸甲酯 | 133130-02-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 4-(甲硫代)丁酸甲酯
• 英文名称: METHYL 4-(METHYLTHIO)BUTYRATE
• CAS: 133130-02-6
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: OGTPRMMHEOKFSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  218.1±9.0 °C(Predicted)
• 密度：
  0.862±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-(甲硫代)丁酸甲酯 在 偶氮二异丁腈 三正丁基氢锡 、 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 4.5h， 生成 7-methyl-5-(2-propenyl)-3-oxabicyclo<3.3.0>octane-2-thione
  参考文献：
  名称：

  Tandem radical cyclization of acyclic homoallylic xanthates: cyclopentannulated .gamma.-thionolactone and .gamma.-lactones

  摘要：

  The first tandem radical cyclization of linear homoallylic xanthates was explored. Homoallylic xanthates prepared from alpha,beta-unsaturated esters were easily cyclized by tin hydride with an radical initiator to give the corresponding thionolactone annulated cyclopentane skeleton in a high yield. The stereochemistry of cyclized products was also discussed. Thionolactones obtained were oxidized chemoselectivity with m-CPBA under neutral condition to afford gamma-lactones in a high yield.

  DOI：

  10.1021/jo00008a048
• 作为产物：
  描述：

  2-vinyl-4-pentenoate 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 反应 0.58h， 生成 4-(甲硫代)丁酸甲酯
  参考文献：
  名称：

  Tandem radical cyclization of acyclic homoallylic xanthates: cyclopentannulated .gamma.-thionolactone and .gamma.-lactones

  摘要：

  The first tandem radical cyclization of linear homoallylic xanthates was explored. Homoallylic xanthates prepared from alpha,beta-unsaturated esters were easily cyclized by tin hydride with an radical initiator to give the corresponding thionolactone annulated cyclopentane skeleton in a high yield. The stereochemistry of cyclized products was also discussed. Thionolactones obtained were oxidized chemoselectivity with m-CPBA under neutral condition to afford gamma-lactones in a high yield.

  DOI：

  10.1021/jo00008a048

文献信息

• New radical reactions of S-alkoxycarbonyl xanthates. Total synthesis of (±)-cinnamolide and (±)-methylenolactocin
  作者：Judith E Forbes、Radomir N Saicic、Samir Z Zard

  DOI：10.1016/s0040-4020(98)01184-3

  日期：1999.3

  with visible light of S-alkoxycarbonyl xanthates derived from various alcohols gives rise to alkoxycarbonyl radicals with bifurcate reactivity: loss of carbon dioxide leads to deoxygenated derivatives (i.e. alkyl xanthates) whereas intramolecular addition to a suitably located double bond produces lactones; these new reactions were applied to the total synthesis of (±)-cinnamolide and (±)-methylenolactocin

  用可见光照射衍生自各种醇的S-烷氧羰基黄药生成具有分叉反应性的烷氧羰基基团：二氧化碳的损失导致脱氧衍生物（即烷基黄药），而分子内加成至适当位置的双键则产生内酯；这些新的反应被应用于（±）-肉桂酸酯和（±）-甲基烯醇内酯的全合成。