tert-butyl N-[2-[5-[tert-butyl(dimethyl)silyl]oxy-2-chlorophenyl]-4-methylphenyl]carbamate | 151692-24-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl N-[2-[5-[tert-butyl(dimethyl)silyl]oxy-2-chlorophenyl]-4-methylphenyl]carbamate
• CAS: 151692-24-9
• 化学式: C₂₄H₃₄ClNO₃Si
• 分子量: 448.077
• InChiKey: HCZBCTOSFBLBQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.05
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[2-[5-[tert-butyl(dimethyl)silyl]oxy-2-chlorophenyl]-4-methylphenyl]carbamate 在 potassium amide 作用下， 以 氨 为溶剂， 反应 3.0h， 以54%的产率得到3-甲基-6-羟基咔唑
  参考文献：
  名称：

  A Regiospecific Synthesis of Carbazoles via Consecutive Palladium-catalyzed Cross-coupling and Aryne-mediated Cyclization

  摘要：

  A regiospecific synthesis of carbazoles has been developed using palladium-catalyzed cross-coupling of N-(tert-butoxycarbonyl)-2-tributylstannylanilines with 2- or 3-bromochlorobenzene followed by aryne-mediated cyclization as the key reactions. The carbazole alkaloids, glycozolinine and glycozolidine, were synthesized using this procedure.

  DOI：

  10.3987/com-93-6368
• 作为产物：
  描述：

  tert-butyl(4-chlorophenoxy)dimethylsilane 在 bis-triphenylphosphine-palladium(II) chloride 、 1,1,2,2-四氟-1,2-二溴乙烷 、 三丁基氯化锡 、 叔丁基锂 、 仲丁基锂 作用下， 反应 2.0h， 生成 tert-butyl N-[2-[5-[tert-butyl(dimethyl)silyl]oxy-2-chlorophenyl]-4-methylphenyl]carbamate
  参考文献：
  名称：

  A Regiospecific Synthesis of Carbazoles via Consecutive Palladium-catalyzed Cross-coupling and Aryne-mediated Cyclization

  摘要：

  A regiospecific synthesis of carbazoles has been developed using palladium-catalyzed cross-coupling of N-(tert-butoxycarbonyl)-2-tributylstannylanilines with 2- or 3-bromochlorobenzene followed by aryne-mediated cyclization as the key reactions. The carbazole alkaloids, glycozolinine and glycozolidine, were synthesized using this procedure.

  DOI：

  10.3987/com-93-6368

文献信息

• A Regiospecific Synthesis of Carbazoles via Consecutive Palladium-catalyzed Cross-coupling and Aryne-mediated Cyclization
  作者：Masatomo Iwao、Hirokazu Takehara、Sunao Furukawa、Mitsuaki Watanabe

  DOI：10.3987/com-93-6368

  日期：——

  A regiospecific synthesis of carbazoles has been developed using palladium-catalyzed cross-coupling of N-(tert-butoxycarbonyl)-2-tributylstannylanilines with 2- or 3-bromochlorobenzene followed by aryne-mediated cyclization as the key reactions. The carbazole alkaloids, glycozolinine and glycozolidine, were synthesized using this procedure.