[(Z)-2-ethoxyethenyl]sulfanylbenzene | 59377-29-6

• 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)-2-ethoxyethenyl]sulfanylbenzene
• CAS: 59377-29-6
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: ADNDITFFQYRIMW-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(Z)-2-ethoxyethenyl]sulfanylbenzene 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 ((Z)-1-Diethoxymethyl-3,3-dimethyl-but-1-enylsulfanyl)-benzene
  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

文献信息

• The OSM (oxidation state modification) concept: Application to a new and rapid synthesis of retinoids
  作者：Lucette Duhamel、Pierre Duhamel、Jean-Erick Ancel

  DOI：10.1016/0040-4039(94)88025-5

  日期：1994.2

  The OSM (oxidation state modification) concept for the elaboration of new synthetic pathways is demonstrated for the synthesis of β-ionylidene acetaldehyde 11 and retinal 13. According to this new scheme, electrophilic addition to ω-heterosubstituted enol ethers 5 of the cationic species 9, generated from β-ionol led to aldehydic intermediates 10 which undergo easy elimination to β-ionylidene acetaldehyde

  OSM（氧化态修饰）概念用于阐述新的合成途径，已被证明可用于合成β-亚砜基乙醛11和视网膜13。根据该新方案，由β-紫罗兰醇向阳离子物种9的ω-杂取代的烯醇醚5中的亲电子加成导致醛中间体10，其易于被消除为β-紫罗兰乙醛11。类似地，经由醛16从乙烯基-β-紫罗兰醇14和二烯醇醚12获得视网膜13。
• 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.