4-((phenylselanyl)methyl)chromane | 1167445-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-((phenylselanyl)methyl)chromane
• 英文别名: 4-(phenylselenylmethyl)chroman；4-(phenylselanylmethyl)-3,4-dihydro-2H-chromene
• CAS: 1167445-32-0
• 化学式: C₁₆H₁₆OSe
• 分子量: 303.262
• InChiKey: VJBAUEVUEGZRSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-phenoxy-1-butene 、 苯基溴化硒 在 silver hexafluoroantimonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 以97%的产率得到4-((phenylselanyl)methyl)chromane
  参考文献：
  名称：

  Seleniranium Ion-Triggered Reactions: New Aspects of Friedel−Crafts and N-Detosylative Cyclizations

  摘要：

  Seleniranium ions at low temperatures (-90 to -78 degrees C) will initiate effective Friedel-Crafts cyclization if a suitably placed arene is allowed to react even when the arene is unactivated. These intermediates generated from N-aryl-N-tosylamides undergo a novel, surprisingly efficient, detosylative cyclization to form 5- or 6-membered nitrogen heterocycles. A debenzylation route is preferred if both benzyl and tosyl groups are present in the substrate.

  DOI：

  10.1021/ol900961m

文献信息

• FeCl₃-Catalyzed Regio-Divergent Carbosulfenylation of Unactivated Alkenes: Construction of a Medium-Sized Ring
  作者：Leiyang Lv、Zhiping Li

  DOI：10.1021/acs.joc.8b01621

  日期：2018.9.21

  carbosulfenylation of unactivated alkenes with electrophilic N-sulfenophthalimides has been developed. This protocol provides a straightforward and efficient access to various medium-sized rings, especially strained 7- and 8-membered carborings with a sulfur atom attached. The endo/exo selectivity in the reaction depends on the atom number of the chain between arene and alkene. Broad substrate scope, high

  已经开发出具有FeCl 3的亲电性N-磺基邻苯二甲酰亚胺催化的未活化烯烃的区域发散性碳亚磺酰基化。该协议可直接有效地访问各种中型环，尤其是带有硫原子的7或8元拉紧的碳环。反应中的内/外选择性取决于芳烃和烯烃之间链的原子数。广泛的底物范围，高收率和克级合成证明了该方案的实用性和实用性。另外，该方法可以扩展到分离的烯烃的碳硒烯基化。
• Seleniranium Ion-Triggered Reactions: New Aspects of Friedel−Crafts and N-Detosylative Cyclizations
  作者：Hwan Jung Lim、T. V. RajanBabu

  DOI：10.1021/ol900961m

  日期：2009.7.2

  Seleniranium ions at low temperatures (-90 to -78 degrees C) will initiate effective Friedel-Crafts cyclization if a suitably placed arene is allowed to react even when the arene is unactivated. These intermediates generated from N-aryl-N-tosylamides undergo a novel, surprisingly efficient, detosylative cyclization to form 5- or 6-membered nitrogen heterocycles. A debenzylation route is preferred if both benzyl and tosyl groups are present in the substrate.