3,5-dimethyl-4-methoxymethoxy-5-[(E)-3-oxooct-1-enyl]-5H-thiophen-2-one | 890933-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢噻吩类
• 英文名称: 3,5-dimethyl-4-methoxymethoxy-5-[(E)-3-oxooct-1-enyl]-5H-thiophen-2-one
• 英文别名: 4-(methoxymethoxy)-3,5-dimethyl-5-[(E)-3-oxooct-1-enyl]thiophen-2-one
• CAS: 890933-80-9
• 化学式: C₁₆H₂₄O₄S
• 分子量: 312.43
• InChiKey: SJOQYZSEFCUMDL-MDZDMXLPSA-N

物化性质

• 沸点：
  455.9±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-dimethyl-4-methoxymethoxy-5-[(E)-3-oxooct-1-enyl]-5H-thiophen-2-one 在 polymer-bound TsOH 、 silica gel 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 3,5-dimethyl-5-(3-pentylbuta-1,3-dienyl)-5H-thiophene-2-one
  参考文献：
  名称：

  Novel route to 5-position vinyl derivatives of thiolactomycin: olefination versus deformylation

  摘要：

  Vinyl and diene derivatives of thiolactomycin have been prepared via Horner-Wadsworth-Emmons olefination from protected 5-formyl-3,5-dimethylthiotetronic acid. Several 4-position protecting groups and a variety of phosphonates were evaluated, with MOM protection and beta-ketophosphonates yielding the highest ratio of the desired product to deformylated product. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.058
• 作为产物：
  描述：

  3,5-dimethyl-4-(methoxymethoxy)-5H-thiophen-2-one 在 戴斯-马丁氧化剂 、 N,N-二异丙基乙胺 、 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.5h， 生成 3,5-dimethyl-4-methoxymethoxy-5-[(E)-3-oxooct-1-enyl]-5H-thiophen-2-one
  参考文献：
  名称：

  Novel route to 5-position vinyl derivatives of thiolactomycin: olefination versus deformylation

  摘要：

  Vinyl and diene derivatives of thiolactomycin have been prepared via Horner-Wadsworth-Emmons olefination from protected 5-formyl-3,5-dimethylthiotetronic acid. Several 4-position protecting groups and a variety of phosphonates were evaluated, with MOM protection and beta-ketophosphonates yielding the highest ratio of the desired product to deformylated product. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.058

文献信息

• Novel route to 5-position vinyl derivatives of thiolactomycin: olefination versus deformylation
  作者：Pilho Kim、Clifton E. Barry、Cynthia S. Dowd

  DOI：10.1016/j.tetlet.2006.03.058

  日期：2006.5

  Vinyl and diene derivatives of thiolactomycin have been prepared via Horner-Wadsworth-Emmons olefination from protected 5-formyl-3,5-dimethylthiotetronic acid. Several 4-position protecting groups and a variety of phosphonates were evaluated, with MOM protection and beta-ketophosphonates yielding the highest ratio of the desired product to deformylated product. (c) 2006 Elsevier Ltd. All rights reserved.