3-[(4-甲基苯基)磺酰基]吡咯并[1,2-c]嘧啶 | 70380-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-[(4-甲基苯基)磺酰基]吡咯并[1,2-c]嘧啶
• 英文名称: 3-[(4-methylphenyl)sulfonyl]pyrrolo[1,2-c]pyrimidine
• 英文别名: 2-tosylpyrrolo<1,2-c>pyrimidine；3-tosylpyrrolo[1,2-c]pyrimidine；3-(toluene-4-sulfonyl)-pyrrolo[1,2-c]pyrimidine；3-Tosylpyrrolo<1,2-c>pyrimidin；3-(4-methylphenyl)sulfonylpyrrolo[1,2-c]pyrimidine
• CAS: 70380-76-6
• 化学式: C₁₄H₁₂N₂O₂S
• 分子量: 272.327
• InChiKey: BZKWJXSPTMRDGK-UHFFFAOYSA-N

物化性质

• 熔点：
  200-202 °C(Solv: acetonitrile (75-05-8))
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(4-甲基苯基)磺酰基]吡咯并[1,2-c]嘧啶 在 disodium hydrogenphosphate 、 sodium amalgam 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.0h， 生成 1-methylpyrrolo[1,2-c]pyrimidine
  参考文献：
  名称：

  Pyrrolodiazines. 5. Synthesis, Structure, and Chemistry of Pyrrolo[1,2-c]pyrimidine. Dipolar Cycloaddition of Pyrrolo[1,2-c]pyrimidinium Ylides

  摘要：

  An improved synthesis of pyrrolo[1,2-c]pyrimidines, including the parent system, was accomplished via sequential condensation of substituted pyrrole-2-carboxaldehydes with tosylmethyl isocyanide (TOSMIC), followed by desulfonylation of the formed tosylpyrrolo[1,2-c]pyrimidines. Based on the ab initio calculations performed on the pyrrolo[1,2-c]pyrimidine 1a, some of the basic chemistry was investigated including electrophilic substitution, addition of organolithium reagents, metalation with lithium diisopropylamide (LDA) and subsequent reaction with electrophiles, and formation of salts by quaternization of the nonbridgehead nitrogen. Azomethine ylides generated from pyrrolo[1,2-c]pyrimidinium salts undergo 1,3-dipolar cycloaddition with suitable dipolarophiles to give new dipyrrolo[1,2-a;1',2'-c]pyrimidine derivatives, with high regio- and stereoselectivity.

  DOI：

  10.1021/jo9907080
• 作为产物：
  描述：

  2-吡咯甲醛 、 4-甲苯磺酰乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以82%的产率得到3-[(4-甲基苯基)磺酰基]吡咯并[1,2-c]嘧啶
  参考文献：
  名称：

  Pyrrolodiazines. 5. Synthesis, Structure, and Chemistry of Pyrrolo[1,2-c]pyrimidine. Dipolar Cycloaddition of Pyrrolo[1,2-c]pyrimidinium Ylides

  摘要：

  An improved synthesis of pyrrolo[1,2-c]pyrimidines, including the parent system, was accomplished via sequential condensation of substituted pyrrole-2-carboxaldehydes with tosylmethyl isocyanide (TOSMIC), followed by desulfonylation of the formed tosylpyrrolo[1,2-c]pyrimidines. Based on the ab initio calculations performed on the pyrrolo[1,2-c]pyrimidine 1a, some of the basic chemistry was investigated including electrophilic substitution, addition of organolithium reagents, metalation with lithium diisopropylamide (LDA) and subsequent reaction with electrophiles, and formation of salts by quaternization of the nonbridgehead nitrogen. Azomethine ylides generated from pyrrolo[1,2-c]pyrimidinium salts undergo 1,3-dipolar cycloaddition with suitable dipolarophiles to give new dipyrrolo[1,2-a;1',2'-c]pyrimidine derivatives, with high regio- and stereoselectivity.

  DOI：

  10.1021/jo9907080

文献信息

• New CRTh2 antagonists
  申请人：Almirall, S.A.

  公开号：EP2548876A1

  公开（公告）日：2013-01-23

  The present invention relates to compounds of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.

  本发明涉及式(I)的化合物，制备这种化合物的方法以及它们在治疗病理状况或疾病中的应用，该病理状况或疾病容易通过CRTh2拮抗活性得到改善。
• [EN] NEW CRTH2 ANTAGONISTS<br/>[FR] NOUVEAUX ANTAGONISTES DE CRTH2
  申请人：ALMIRALL SA

  公开号：WO2013010880A1

  公开（公告）日：2013-01-24

  The present invention relates to compounds of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.

  本发明涉及式(I)的化合物，以及制备这种化合物的方法，以及它们在治疗病理状况或疾病中的应用，这些病理状况或疾病容易通过CRTh2拮抗活性得到改善。
• Improved synthesis of pyrrolo[1,2-c]pyrimidine and derivatives
  作者：JoséM. Minguez、Juan J. Vaquero、JoséL. García-Navio、Julio Alvarez-Builla

  DOI：10.1016/0040-4039(96)00812-x

  日期：1996.6

  An improved synthesis of pyrrolo[1,2-c]pyrimidine derivatives by cyclocondensation of pyrrole-2-carboxaldehydes with tosylmethyl isocyanide followed by desulfonylation of the resulting 2-tosylpyrrolo[1,2-c]-pyrimidines with sodium amalgam is described

  描述了一种改进的合成吡咯并[1,2- c ]嘧啶衍生物的方法，该方法是将吡咯-2-羧酸与甲苯磺酰基甲基异氰酸酯进行环缩合，然后将所得的2-甲苯磺酰基吡咯并[1,2 - c ]-嘧啶与汞齐钠进行磺酰化
• Pyrrolodiazines. 5. Synthesis, Structure, and Chemistry of Pyrrolo[1,2-<i>c</i>]pyrimidine. Dipolar Cycloaddition of Pyrrolo[1,2-<i>c</i>]pyrimidinium Ylides
  作者：José M. Minguez、Juan J. Vaquero、Julio Alvarez-Builla、Obis Castaño、José L. Andrés

  DOI：10.1021/jo9907080

  日期：1999.10.1

  An improved synthesis of pyrrolo[1,2-c]pyrimidines, including the parent system, was accomplished via sequential condensation of substituted pyrrole-2-carboxaldehydes with tosylmethyl isocyanide (TOSMIC), followed by desulfonylation of the formed tosylpyrrolo[1,2-c]pyrimidines. Based on the ab initio calculations performed on the pyrrolo[1,2-c]pyrimidine 1a, some of the basic chemistry was investigated including electrophilic substitution, addition of organolithium reagents, metalation with lithium diisopropylamide (LDA) and subsequent reaction with electrophiles, and formation of salts by quaternization of the nonbridgehead nitrogen. Azomethine ylides generated from pyrrolo[1,2-c]pyrimidinium salts undergo 1,3-dipolar cycloaddition with suitable dipolarophiles to give new dipyrrolo[1,2-a;1',2'-c]pyrimidine derivatives, with high regio- and stereoselectivity.