methyl 4-methylene-6-(phenylthio)hexanoate | 160189-64-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methyl 4-methylene-6-(phenylthio)hexanoate
• CAS: 160189-64-0
• 化学式: C₁₄H₁₈O₂S
• 分子量: 250.362
• InChiKey: BOGZEMKYVFTGKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 4-methylene-6-(phenylthio)hexanoate 在 4-二甲氨基吡啶 、 sodium chlorite 、 lithium aluminium tetrahydride 、 sodium amalgam 、 二苯基二硒醚 、 四丁基氟化铵 、 双氧水 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 生成 methyl O,O-isopropylidenealternarate
  参考文献：
  名称：

  Total synthesis of alternaric acid

  摘要：

  A total synthesis of alternaric acid (1) has been achieved. Key reactions include the Julia olefination of tertiary aldehyde 4 and phenylsulfone 5, and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydropyrone via Fries type rearrangement of O-enolacyl group of beta-keto-delta-valerolactone toward alpha-position of the delta-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1.

  DOI：

  10.1016/s0040-4039(00)77605-2
• 作为产物：
  描述：

  1,4-diacetoxy-2-methylenebutane 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 吡啶 、 三丁基膦 、 水 、 sodium hydride 、 对甲苯磺酸 、 1,2-双(二苯基膦)乙烷 、 sodium chloride 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 35.0h， 生成 methyl 4-methylene-6-(phenylthio)hexanoate
  参考文献：
  名称：

  Total Synthesis and Stereochemistry of Alternaric Acid

  摘要：

  Determination of the stereochemistry and the total synthesis of alternaric acid 1 has been achieved. The stereostructure of 1 has been elucidated by stereoselective synthesis of four diastereoisomers of the C(9)-C(14) fragment 6, which had been obtained as a degradation product during structural studies. Key reactions of the total synthesis of 1 include the Julia olefination of tertiary aldehyde 6 and phenylsulfone 7 and novel one-pot construction of 3-acyl-4-hydroxy-5,6-dihydro-2-pyrone via Fries-type rearrangement of the O-enol acyl group of beta-keto-delta-valerolactone toward the a-position of the delta-lactone. The absolute configuration of alternaric acid has been shown to be that illustrated in structure 1. The modified Fries-type rearrangement method has also been extended to the synthesis of some other compounds containing a tricarbonylmethane structure.

  DOI：

  10.1021/jo00096a016