2-(2-(p-tolylsulfinyl)ethyl)naphthalene | 1512844-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-(p-tolylsulfinyl)ethyl)naphthalene
• 英文别名: 2-[2-(4-Methylphenyl)sulfinylethyl]naphthalene
• CAS: 1512844-29-9
• 化学式: C₁₉H₁₈OS
• 分子量: 294.417
• InChiKey: MXZWQBKSPCRYLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(2-(p-tolylsulfinyl)ethyl)naphthalene 在 碘苯 、 silver(I) acetate 、 溶剂黄146 、 palladium dichloride 作用下， 以 1,1,2,2-四氯乙烷 为溶剂， 反应 60.0h， 以51%的产率得到2-methyl-6,7-dihydrobenzo[b]naphtho[2,3-d]thiepine 5-oxide
  参考文献：
  名称：

  Synthesis of Sulfur-Bridged Polycycles via Pd-Catalyzed Dehydrogenative Cyclization

  摘要：

  A general approach to sulfur-bridged polycycles by palladium-catalyzed double C(sp(2))-H bond oxidative cyclization is presented. This protocol afforded diverse sulfur-bridged five-, six-, and seven-membered polycycles in moderate to good yields with a tolerance for a wide variety of functional groups. A sulfide-bridged six-membered pyrene-thienoacene compound was synthesized readily using this method, and excellent performance for photoluminescence quantum yield was observed.

  DOI：

  10.1021/ol502127j
• 作为产物：
  描述：

  4-甲苯硫酚 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 2-(2-(p-tolylsulfinyl)ethyl)naphthalene
  参考文献：
  名称：

  Synthesis of Sulfur-Bridged Polycycles via Pd-Catalyzed Dehydrogenative Cyclization

  摘要：

  A general approach to sulfur-bridged polycycles by palladium-catalyzed double C(sp(2))-H bond oxidative cyclization is presented. This protocol afforded diverse sulfur-bridged five-, six-, and seven-membered polycycles in moderate to good yields with a tolerance for a wide variety of functional groups. A sulfide-bridged six-membered pyrene-thienoacene compound was synthesized readily using this method, and excellent performance for photoluminescence quantum yield was observed.

  DOI：

  10.1021/ol502127j

文献信息

• Thiol–ene/oxidation tandem reaction under visible light photocatalysis: synthesis of alkyl sulfoxides
  作者：Andrea Guerrero-Corella、Ana María Martinez-Gualda、Fereshteh Ahmadi、Enrique Ming、Alberto Fraile、José Alemán

  DOI：10.1039/c7cc05672a

  日期：——

  The photocatalyzed synthesis of sulfoxides from alkenes and thiols has been carried out using Eosin Y.

  烯烃和硫醇的光催化合成已经使用Eosin Y进行。
• Palladium(II)-Catalyzed <i>ortho</i>-Olefination of Arenes Applying Sulfoxides as Remote Directing Groups
  作者：Binjie Wang、Chuang Shen、Jinzhong Yao、Hong Yin、Yuhong Zhang

  DOI：10.1021/ol402921w

  日期：2014.1.3

  A novel palladium-catalyzed ortho-C(sp(2))-H olefination protocol has been developed by the use of sulfoxide as the directing group. Importantly, relatively remote coordination can be accessed to achieve the ortho olefination of benzyl, 2-arylethyl, and 3-arylpropenyl sulfoxide substrates, and the olefinated sulfoxide can be easily transformed to other functionalities.