(-)-(S)-2-(E)-4-(Z)-3-methyl-5-phenyl-4-(p-tolylsulfinyl)penta-2,4-dien-1-ol | 1211944-97-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (-)-(S)-2-(E)-4-(Z)-3-methyl-5-phenyl-4-(p-tolylsulfinyl)penta-2,4-dien-1-ol
• 英文别名: (2E,4Z)-3-methyl-4-[(S)-(4-methylphenyl)sulfinyl]-5-phenylpenta-2,4-dien-1-ol
• CAS: 1211944-97-6
• 化学式: C₁₉H₂₀O₂S
• 分子量: 312.433
• InChiKey: YSFBFCKYSRLEIN-JCAKZVABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(S)-2-(E)-4-(Z)-3-methyl-5-phenyl-4-(p-tolylsulfinyl)penta-2,4-dien-1-ol 、 3-溴丙炔 在 苄基三甲基氢氧化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 以53%的产率得到(-)-(S)-7-methyl-4-oxa-9-phenyl-8-(p-tolylsulfinyl)-6-(E)-8-(Z)-nonadien-1-yne
  参考文献：
  名称：

  Sulfoxide-Directed Intramolecular [4 + 2] Cycloadditions between 2-Sulfinyl Butadienes and Unactivated Alkynes

  摘要：

  Sulfinyl dienynes undergo thermal and catalyzed IMDA cycloadditions, often at room temperature, to produce cyclohexa-1,4-dienes with good yields and high selectivities. Additionally, the products preserve a synthetically useful vinyl sulfoxide functionality. The selective manipulation of the double bonds in the cycloadducts has also been examined in this work.

  DOI：

  10.1021/jo9024489
• 作为产物：
  描述：

  (2E)-3-methyl-3-tributylstannylprop-2-en-1-ol 、 (-)-(S)-(E)-2-phenyl-1-(p-tolylsulfinyl)-1-iodoethane 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯胂 、 2,6-二叔丁基-4-甲基苯酚 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以100%的产率得到(-)-(S)-2-(E)-4-(Z)-3-methyl-5-phenyl-4-(p-tolylsulfinyl)penta-2,4-dien-1-ol
  参考文献：
  名称：

  Sulfoxide-Directed Intramolecular [4 + 2] Cycloadditions between 2-Sulfinyl Butadienes and Unactivated Alkynes

  摘要：

  Sulfinyl dienynes undergo thermal and catalyzed IMDA cycloadditions, often at room temperature, to produce cyclohexa-1,4-dienes with good yields and high selectivities. Additionally, the products preserve a synthetically useful vinyl sulfoxide functionality. The selective manipulation of the double bonds in the cycloadducts has also been examined in this work.

  DOI：

  10.1021/jo9024489

文献信息

• Sulfoxide-Directed Intramolecular [4 + 2] Cycloadditions between 2-Sulfinyl Butadienes and Unactivated Alkynes
  作者：Roberto Fernández de la Pradilla、Mariola Tortosa、Esther Castellanos、Alma Viso、Raquel Baile

  DOI：10.1021/jo9024489

  日期：2010.3.5

  Sulfinyl dienynes undergo thermal and catalyzed IMDA cycloadditions, often at room temperature, to produce cyclohexa-1,4-dienes with good yields and high selectivities. Additionally, the products preserve a synthetically useful vinyl sulfoxide functionality. The selective manipulation of the double bonds in the cycloadducts has also been examined in this work.