6,6-dimethyl-5-phenylthio-hepta-1,4(Z)-diene

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6,6-dimethyl-5-phenylthio-hepta-1,4(Z)-diene
• 英文别名: [(3Z)-2,2-dimethylhepta-3,6-dien-3-yl]sulfanylbenzene
• 化学式: C₁₅H₂₀S
• 分子量: 232.39
• InChiKey: MFKXXNSAOPONEE-OWBHPGMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,3-二甲基-1-丁炔 、 烯丙氧基苯硫酚 在 bis(1,5-cyclooctadiene)nickel (0) 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以58%的产率得到6,6-dimethyl-5-phenylthio-hepta-1,4(Z)-diene
  参考文献：
  名称：

  Nickel-Catalyzed Thioallylation of Alkynes with Allyl Phenyl Sulfides

  摘要：

  Allylic sulfides add to alkynes in the presence of nickel complexes efficiently to afford thio-1,4-dienes regio- and stereoselectively. Functional groups such as alkoxy, siloxy, hydroxy, carboalkoxy, chloro, and cyano groups are tolerated. A mechanism that involves a pi-allyl nickel intermediate is proposed on the basis of isolation of pi-allyl complexes and distribution of products in the reactions of alpha- or gamma-methylated allyl sulfide.

  DOI：

  10.1021/ol062686r

文献信息

• Nickel-Catalyzed Thioallylation of Alkynes with Allyl Phenyl Sulfides
  作者：Ruimao Hua、Hideaki Takeda、Shun-ya Onozawa、Yoshimoto Abe、Masato Tanaka

  DOI：10.1021/ol062686r

  日期：2007.1.1

  Allylic sulfides add to alkynes in the presence of nickel complexes efficiently to afford thio-1,4-dienes regio- and stereoselectively. Functional groups such as alkoxy, siloxy, hydroxy, carboalkoxy, chloro, and cyano groups are tolerated. A mechanism that involves a pi-allyl nickel intermediate is proposed on the basis of isolation of pi-allyl complexes and distribution of products in the reactions of alpha- or gamma-methylated allyl sulfide.