N-<(p-chlorophenyl)seleno>phthalimide | 137007-97-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-<(p-chlorophenyl)seleno>phthalimide
• 英文别名: N-phenylselenophthalimide；2-(4-chlorophenyl)selanylisoindole-1,3-dione
• CAS: 137007-97-7
• 化学式: C₁₄H₈ClNO₂Se
• 分子量: 336.636
• InChiKey: RNIWNPCGSAKODV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-ethyl-N-phenylmethacrylamide 、 N-<(p-chlorophenyl)seleno>phthalimide 在 ammonium peroxydisulfate 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以64%的产率得到3-[(4-chlorophenylseleno)methyl]-1-ethyl-3-methylindolin-2-on
  参考文献：
  名称：

  通过有机硒诱导的 N-芳基丙烯酰胺自由基环化合成 3,3-二取代羟吲哚

  摘要：

  摘要 已经开发了一种通过有机硒诱导的 N-芳基丙烯酰胺自由基环化来制备羟吲哚衍生物的简单实用方法。该方法提供了在相对温和的反应条件下以良好至极好的产率获得各种含硒羟吲哚的便利途径。作为其显着特征之一，自由基过程允许直接形成 Se-C 键并在一个反应​​中构建羟吲哚环。

  DOI：

  10.1515/hc-2014-0195

文献信息

• Organocatalytic asymmetric selenofunctionalization of tryptamine for the synthesis of hexahydropyrrolo[2,3-<i>b</i>]indole derivatives
  作者：Qiang Wei、Ya-Yi Wang、Yu-Liu Du、Liu-Zhu Gong

  DOI：10.3762/bjoc.9.177

  日期：——

  A chiral phosphoric acid-catalyzed selenofunctionalization of tryptamine derivatives provides access to 3a-(phenylselenyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole derivatives in high yields and with synthetically useful levels of enantioselectivity (up to 89% ee).

  手性磷酸催化的色胺衍生物硒功能化提供了高产率和合成有用水平的 3a-(苯基硒基)-1,2,3,3a,8,8a-六氢吡咯并[2,3-b]吲哚衍生物对映选择性（高达 89% ee）。
• Preparation and isomerization of 1-phenylseleno 1,3-dienes
  作者：Michael D. Fryzuk、Gordon S. Bates、Charles Stone

  DOI：10.1021/jo00026a006

  日期：1991.12

  The preparation of a series of 1-phenylseleno 1,3-dienes is described starting from enyne derivatives via a hydrozirconation/transfer sequence. Hydrozirconation of a series of conjugated enynes having the general formula HC = CCR1 = CR2R3 (3a: R1 = R2 = R3 = H; 3b: R1 = R3 = H, R2 = OMe; 3c: R1 = R2 = H, R3 = OMe; 3d: R1 = R2 = -(CH2)4-, R3 = H) leads to the formation of zirconium dienyls of the formula (eta-5-C5H5)2Zr(Cl)-CH = CHCR1 = CR2R3, 4a-d, respectively; this reaction is both completely stereoselective and chemoselective. Use of the deuterium-substituted reagent (eta-5-C5H5)2Zr(D)Cl generates the corresponding isotopomers (eta-5-C5H5)2Zr(Cl)-CH = CDCR1 = CR2R3, 4a-d-d1. Addition of PhSeX (X = SePh, Cl, or N-phthalimido) to the zirconium dienyl derivatives 4a-d at low temperature (-20-degrees-C) and in the dark results in the formation of the 1-phenylseleno 1,3-dienes (PhSeCH = CHCR1 = CR2R3 (5a: R1 = R2 = R3 = H; 5b: R1 = R3 = H, R2 = OMe; 5c: R1 = R2 = H, R3 = OMe; 5d: R1 = R2 = -(CH2)4-, R3 = H). This transfer of the dienyl unit from zirconium to selenium proceeds with complete stereoselectivity and with retention of configuration at the 1-position as long as light is excluded and the reaction is carried out at low temperatures. In the presence of room light (fluorescent), mixtures of stereoisomers are obtained for the seleno dienes 5a-c; no apparent isomerization is observed for 5d; similar results are obtained upon thermolysis (80-degrees-C for 24-48 h). The mechanism of this isomerization process was determined to be intermolecular on the basis of crossover experiments; in addition, the use of radical traps established that the process was a radical chain mechanism, probably via addition of PhSe. to the seleno diene followed by single-bond rotation.