(Z)-1-Ethoxy-4,4-dimethyl-2-phenylsulfanyl-pent-1-en-3-ol | 210416-70-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (Z)-1-Ethoxy-4,4-dimethyl-2-phenylsulfanyl-pent-1-en-3-ol
• 英文别名: (Z)-1-ethoxy-4,4-dimethyl-2-phenylsulfanylpent-1-en-3-ol
• CAS: 210416-70-9
• 化学式: C₁₅H₂₂O₂S
• 分子量: 266.404
• InChiKey: HIOVYWGVNOAGFQ-QBFSEMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-1-Ethoxy-4,4-dimethyl-2-phenylsulfanyl-pent-1-en-3-ol 在 正丁基锂 、 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 (2Z,4Z)-6,6-dimethyl-2,4-bis(phenylthio)hepta-2,4-dienal diethyl acetal
  参考文献：
  名称：

  A New 1-Alkoxy-2-(chalcogeno)allylic or 1-Alkoxy-2,4-bis(chalcogeno)penta-2,4-dienyl Cation:  Highly-Regioselective Allylating or Penta-2,4-dienylating Electrophiles and Their Reactions

  摘要：

  2-(Chalcogeno)-1-ethoxyallylic cations 4A are easily generated from the reactions of 2-(chalcogeno)-1-ethoxyprop-1-en-3-ols 2a-e or 2-(chalcogeno)prop-2-enal acetals 3a-c and TMSOTf and reacted with various nucleophiles to give the adducts 5a-8a, 5b-11b, and 5c-e regio and stereoselectively. 2,4-Bis(chalcogeno)penta-2,4-dienal acetals 16a,c and the 2,4,6-tris(phenylthio)hepta-2,4,6-trienal acetal 20c also gave the dienones 17a,c and 21c in good yields. Furthermore, the intramolecular cyclization of the alkenyl alcohols 25a,b and the 2,4-dienal 2,4-dinitrophenyl hydrazones 29a-c afforded the tetrahydrofurans 26a,b and 3,5-bis(chalcogeno)pyridines 30a-c, respectively.

  DOI：

  10.1021/jo9807767
• 作为产物：
  描述：

  [(E)-2-ethoxyethenyl]sulfanylbenzene 、 特戊醛 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到(Z)-1-Ethoxy-4,4-dimethyl-2-phenylsulfanyl-pent-1-en-3-ol
  参考文献：
  名称：

  The First Example of the 1-Chalcogene-Substituted Formylolefination of the Ketones and Aldehydes Using 1-Lithio-2-ethoxyvinyl Chalcogenides

  摘要：

  The alpha-chalcogene-substituted formylolefinations of ketones and aldehydes proceeded using 1-lithio-2-ethoxyvinyl chalcogenides/PPSE or TMSOTf produce the alpha-chalcogenoformylolefinated products 4a-1 in high yields. Tandem-formylolefination provided the (2Z,4Z)-2,4-bis(chalcogeno)pent-2,4-dienals 5d,h,i and (2Z,4Z,6Z)-2,4,6-tris(phenylthio)hept-2, derivatives 7d and 8d, respectively.

  DOI：

  10.1021/jo980487i

文献信息

• The First Example of the 1-Chalcogene-Substituted Formylolefination of the Ketones and Aldehydes Using 1-Lithio-2-ethoxyvinyl Chalcogenides
  作者：Mitsuhiro Yoshimatsu、Kiyomi Oguri、Kazunari Ikeda、Satoshi Gotoh

  DOI：10.1021/jo980487i

  日期：1998.6.1

  The alpha-chalcogene-substituted formylolefinations of ketones and aldehydes proceeded using 1-lithio-2-ethoxyvinyl chalcogenides/PPSE or TMSOTf produce the alpha-chalcogenoformylolefinated products 4a-1 in high yields. Tandem-formylolefination provided the (2Z,4Z)-2,4-bis(chalcogeno)pent-2,4-dienals 5d,h,i and (2Z,4Z,6Z)-2,4,6-tris(phenylthio)hept-2, derivatives 7d and 8d, respectively.
• A New 1-Alkoxy-2-(chalcogeno)allylic or 1-Alkoxy-2,4-bis(chalcogeno)penta-2,4-dienyl Cation:  Highly-Regioselective Allylating or Penta-2,4-dienylating Electrophiles and Their Reactions
  作者：Mitsuhiro Yoshimatsu、Satoshi Gotoh、Kazunari Ikeda、Motonori Komori

  DOI：10.1021/jo9807767

  日期：1998.9.1

  2-(Chalcogeno)-1-ethoxyallylic cations 4A are easily generated from the reactions of 2-(chalcogeno)-1-ethoxyprop-1-en-3-ols 2a-e or 2-(chalcogeno)prop-2-enal acetals 3a-c and TMSOTf and reacted with various nucleophiles to give the adducts 5a-8a, 5b-11b, and 5c-e regio and stereoselectively. 2,4-Bis(chalcogeno)penta-2,4-dienal acetals 16a,c and the 2,4,6-tris(phenylthio)hepta-2,4,6-trienal acetal 20c also gave the dienones 17a,c and 21c in good yields. Furthermore, the intramolecular cyclization of the alkenyl alcohols 25a,b and the 2,4-dienal 2,4-dinitrophenyl hydrazones 29a-c afforded the tetrahydrofurans 26a,b and 3,5-bis(chalcogeno)pyridines 30a-c, respectively.