1-(1-Methylene-indan-2-yl)-4-phenyl-[1,2,4]triazolidine-3,5-dione | 117034-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(1-Methylene-indan-2-yl)-4-phenyl-[1,2,4]triazolidine-3,5-dione
• 英文别名: 1-(3-methylidene-1,2-dihydroinden-2-yl)-4-phenyl-1,2,4-triazolidine-3,5-dione
• CAS: 117034-22-7
• 化学式: C₁₈H₁₅N₃O₂
• 分子量: 305.336
• InChiKey: QGOBGBREGKKZRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  59.79
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-methylindan-2-one 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-(1-Methylene-indan-2-yl)-4-phenyl-[1,2,4]triazolidine-3,5-dione
  参考文献：
  名称：

  Reactions of Phenyltriazolinedione with Alkenes. Stereochemistry of Methanol Adducts to Aziridinium Imide Intermediates

  摘要：

  The addition of 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) and the stereochemistry of methanol/PTAD adduct formation with cis- and trans-2-butenes, 1-methylcyclopentene, (E)-2-methyl-2-butene-1,1,1-d(3), and substituted indenes (indene, 2-methylindene, 2,3-dimethylindene) have been investigated. There is no loss of stereochemistry in the addition of MeOH and PTAD to butenes, 1-methylcyclopentene, 2-methyl-2-butene, and indene. However, in methyl-substituted indenes 9 and 14, loss of stereochemistry at the reaction center is observed. An aziridinium imide (AI) is proposed as an intermediate in all these systems. The stability of the AI intermediate and its equilibration with an open zwitterion depend on the particular system. Only in the benzylically-stabilized tertiary indenes is the open zwitterion stable enough to cause loss of stereochemistry.

  DOI：

  10.1021/ja00132a006

文献信息

• Reaction of 4-phenyl-1,2,4-triazoline-3,5-dione with substituted indenes
  作者：Ioulia Smonou、Michael Orfanopoulos、Christopher S. Foote

  DOI：10.1016/0040-4039(88)85204-3

  日期：1988.1

  4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) reacts with 2,3-dimethyl and 2-methylindene at low temperature mainly to give 1,2-addition products. These products interconvert, then isomerise completely to the ene adducts in solution at RT. In methanol, solvent adducts are formed that also convert to the ene product.

  4-苯基-1,2,4-三唑啉-3,5-二酮（PTAD）在低温下与2,3-二甲基和2-甲基茚反应，主要生成1,2-加成产物。这些产物相互转化，然后在室温下完全异构化为溶液中的烯烃加合物。在甲醇中，形成了溶剂加合物，该加合物也转化为烯产物。