3-[2-(Benzotriazol-1-ylmethyl)-4-tert-butylpyrrol-1-yl]propan-1-ol | 188829-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 3-[2-(Benzotriazol-1-ylmethyl)-4-tert-butylpyrrol-1-yl]propan-1-ol
• CAS: 188829-83-6
• 化学式: C₁₈H₂₄N₄O
• 分子量: 312.415
• InChiKey: IODZKHMCOANHRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[2-(Benzotriazol-1-ylmethyl)-4-tert-butylpyrrol-1-yl]propan-1-ol 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 3-[8-(benzotriazol-1-yl)-2-tert-butyl-6,7-dihydro-5H-indolizin-8-yl]-1,3-diphenylpropan-1-one
  参考文献：
  名称：

  General and Efficient Approaches to Fused [1,2-a]Pyrroles and [1,2-a]Indoles

  摘要：

  2-[(Benzotriazol-1-yl)methyl]pyrroles 4a-c, and 15a,b and -indoles 23, prepared as previously reported,(1,2) were converted into the corresponding fused [1,2-a]pyrroles 8a-c, and 18a,b and fused [1,2-a]indoles 25, 27 by intramolecular cyclizations; the formations of 25 and 27 involve [3 + 2] and [3 + 3] annulations. The benzotriazoly-CH-ring moieties of intermediates 8a,b, 18a,b, 25, and 27 were further elaborated: (i) acylation of 8a and subsequent reduction and elimination promoted by LiAlH4 to give product 6; (ii) nucleophilic displacements of the benzotriazolyl moiety with NaCN, NaSPh, and Grignard reagents to afford compounds 9, 11, 12, 20, 29, and 32, respectively; (iii) base-assisted eliminations of benzotriazole from 8b and 18a to form the unsaturated fused [1,2-a]pyrroles 10 and 17; (iv) reactions of 18b and 25 with alpha,beta-unsaturated ketone and aldehyde followed by acid-assisted elimination of the benzotriazolyl group to yield tricyclic compound 21 and product 31; and (v) Lewis acid promoted dimerization of 27 to form the fused indolo[3,2-b]carbazole 33.

  DOI：

  10.1021/jo9623191
• 作为产物：
  描述：

  1-(2-炔丙基 在 正丁基锂 作用下， 以 异丙醇 为溶剂， 反应 44.5h， 生成 3-[2-(Benzotriazol-1-ylmethyl)-4-tert-butylpyrrol-1-yl]propan-1-ol
  参考文献：
  名称：

  General and Efficient Approaches to Fused [1,2-a]Pyrroles and [1,2-a]Indoles

  摘要：

  2-[(Benzotriazol-1-yl)methyl]pyrroles 4a-c, and 15a,b and -indoles 23, prepared as previously reported,(1,2) were converted into the corresponding fused [1,2-a]pyrroles 8a-c, and 18a,b and fused [1,2-a]indoles 25, 27 by intramolecular cyclizations; the formations of 25 and 27 involve [3 + 2] and [3 + 3] annulations. The benzotriazoly-CH-ring moieties of intermediates 8a,b, 18a,b, 25, and 27 were further elaborated: (i) acylation of 8a and subsequent reduction and elimination promoted by LiAlH4 to give product 6; (ii) nucleophilic displacements of the benzotriazolyl moiety with NaCN, NaSPh, and Grignard reagents to afford compounds 9, 11, 12, 20, 29, and 32, respectively; (iii) base-assisted eliminations of benzotriazole from 8b and 18a to form the unsaturated fused [1,2-a]pyrroles 10 and 17; (iv) reactions of 18b and 25 with alpha,beta-unsaturated ketone and aldehyde followed by acid-assisted elimination of the benzotriazolyl group to yield tricyclic compound 21 and product 31; and (v) Lewis acid promoted dimerization of 27 to form the fused indolo[3,2-b]carbazole 33.

  DOI：

  10.1021/jo9623191

文献信息

• General and Efficient Approaches to Fused [1,2-<i>a</i>]Pyrroles and [1,2-<i>a</i>]Indoles
  作者：Alan R. Katritzky、Clara N. Fali、Jianqing Li

  DOI：10.1021/jo9623191

  日期：1997.6.13

  2-[(Benzotriazol-1-yl)methyl]pyrroles 4a-c, and 15a,b and -indoles 23, prepared as previously reported,(1,2) were converted into the corresponding fused [1,2-a]pyrroles 8a-c, and 18a,b and fused [1,2-a]indoles 25, 27 by intramolecular cyclizations; the formations of 25 and 27 involve [3 + 2] and [3 + 3] annulations. The benzotriazoly-CH-ring moieties of intermediates 8a,b, 18a,b, 25, and 27 were further elaborated: (i) acylation of 8a and subsequent reduction and elimination promoted by LiAlH4 to give product 6; (ii) nucleophilic displacements of the benzotriazolyl moiety with NaCN, NaSPh, and Grignard reagents to afford compounds 9, 11, 12, 20, 29, and 32, respectively; (iii) base-assisted eliminations of benzotriazole from 8b and 18a to form the unsaturated fused [1,2-a]pyrroles 10 and 17; (iv) reactions of 18b and 25 with alpha,beta-unsaturated ketone and aldehyde followed by acid-assisted elimination of the benzotriazolyl group to yield tricyclic compound 21 and product 31; and (v) Lewis acid promoted dimerization of 27 to form the fused indolo[3,2-b]carbazole 33.