2-硝基-3-苯基吲哚 | 40731-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-硝基-3-苯基吲哚
• 英文名称: 2-nitro-3-phenylindole
• 英文别名: 2-nitro-3-phenyl-1H-indole
• CAS: 40731-28-0
• 化学式: C₁₄H₁₀N₂O₂
• 分子量: 238.246
• InChiKey: QTNOGDJLOZFIAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(pyridine-2-carbonyl)-3-phenylindole 在 亚硝酸特丁酯 、 copper dichloride 作用下， 以 1,4-二氧六环 为溶剂， 以81%的产率得到2-硝基-3-苯基吲哚
  参考文献：
  名称：

  一种制备2-硝基吲哚衍生物的方法

  摘要：

  本发明公开了一种制备2‑硝基吲哚衍生物的方法。本发明使用吡啶甲酰基吲哚为起始物，原料易得，种类广泛；利用本发明方法得到的产物类型多样，用途广泛，既可直接使用，又可用于合成药物；此外，本发明公开的方法步骤简单、反应条件温和、目标产物的收率高、污染小、反应操作和后处理过程简单，适合于工业化生产。

  公开号：

  CN108689907B

文献信息

• Addition, substitution and deoxygenation reactions of .alpha.-phenyl-.beta.-nitrostyrenes with the anions of thiols and diethyl phosphite: formation of indoles by reaction with ethyl phosphites
  作者：Glen A. Russell、Ching Fa Yao、Hasan I. Tashtoush、June E. Russell、Douglas F. Dedolph

  DOI：10.1021/jo00002a032

  日期：1991.1

  Reactions of excess RS- (R = Ph, t-Bu) with Ph2C = C(SPh)NO2 in Me2SO form Ph2C = CHSR via conversion of the initial Micheal-type adducts into Ph2C(SR)CH = NO2- and Ph2C = CHNO2. In a similar fashion, reaction of (EtO)2PO- with Ph2C = C(SPh)NO2 forms initially mainly PhSP(O) (OEt)2 and PH2C[P(O)(OEt)2]CH = NO2-, which upon acidic workup will yield the nitroalkane or the Nef reaction product, Ph2C[P(O)(OEt)2]CHO. The reaction of (EtO)2PO- with Ph2C = C(SPh)NO2 also produces Ph2C[P(O)(OEt)2] C = N via a perkow-type reaction of the Michael adduct to yield Ph2C[P(O)(OEt)2]CH = N(O)OP(O)(OEt)2 as an intermediate. The nitrile is also formed from Ph2C[P(O)(OEt)2]CH(NO2)2 with (EtO)2PO- in (EtO)2P(O)H or Me2SO at 30-degrees-C and in > 95% yield by the reaction of (EtO)3P with Ph2C[P(O)(OEt)2CH(NO2)2 at 150-degrees-C. Reaction of Ph2C = CHNO2 or Ph2C[P(O)(OEt)2]CH2NO2 with excess (EtO)2PO- in Me2SO or (EtO)2P(O)H forms 3-(diethoxyphosphinyl)-2,2-diphenylaziridine by a process postulated to involve Ph2C = CHN(O-)OP(O)(OEt)2, Ph2C = CHNOP(O)(OEt)2-, and 2,2-diphenyl-2H-azirine. Similarly, Ph2C = C(SBu-t)NO2 and (EtO)2PO- give 3-(tert-butylthio)-2,2-diphenyl-2H-azirine in Me2SO or 2-(tert-butylthio)-3-phenylindole in (EtO)2P(O)H solution. Deoxygenation of Ph2C = C(X)NO2 to form the 2-X-3-phenylindoles occurs in high yield at 150-degrees-C in (EtO)3P with X = H, PhS, or t-BuS while 2-nitro-3-phenylindole is formed from Ph2C = C(NO2)2 in (EtO)2P(O)H at 150-degrees-C.