1-Acetoxy-9-methylcarbazole | 132376-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-Acetoxy-9-methylcarbazole
• 英文别名: (9-Methylcarbazol-1-yl) acetate
• CAS: 132376-82-0
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: AZYBSTDFURZIER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-<1-(methoxymethyl)-3-indolyl>allyl acetate 在 bis-triphenylphosphine-palladium(II) chloride 一氧化碳 、 乙酸酐 、 三乙胺 作用下， 以 苯 为溶剂， 130.0 ℃ 、6.86 MPa 条件下， 反应 1.5h， 以53%的产率得到1-Acetoxy-9-(methoxymethyl)carbazole
  参考文献：
  名称：

  Construction of polycyclic compounds by cyclocarbonylation. 6. Palladium-catalyzed cyclocarbonylation of 3-(heteroaryl)allyl acetates

  摘要：

  Acetoxybenzofurans, acetoxybenzothiophenes, acetoxyindoles, and acetoxycarbazoles were obtained in high yields by cyclocarbonylation of 3-furyl-, 3-thienyl-, 3-pyrrolyl-, and 3-indolylallyl acetates, respectively, in the presence of Ac2O, NEt3, and a catalytic amount of PdCl2(PPh3)2 at 130-170-degrees-C under 50-70 atm of CO. 3-(3-Furyl)allyl and 3-(3-thienyl)allyl acetates cyclized selectively at the 2-position of the heterocyclic nucleus to give 7-acetoxybenzofuran and 7-acetoxybenzothiophene, respectively. The synthetic utility of the reaction was demonstrated by the synthesis of cannabifuran from isothymol.

  DOI：

  10.1021/jo00005a046

文献信息

• IWASAKI, MASAKAZU;KOBAYASHI, YOSHIHIRO;LI, JI-PING;MATSUZAKA, HIROYUKI;IS+, J. ORG. CHEM., 56,(1991) N, C. 1922-1927
  作者：IWASAKI, MASAKAZU、KOBAYASHI, YOSHIHIRO、LI, JI-PING、MATSUZAKA, HIROYUKI、IS+

  DOI：——

  日期：——
• Construction of polycyclic compounds by cyclocarbonylation. 6. Palladium-catalyzed cyclocarbonylation of 3-(heteroaryl)allyl acetates
  作者：Masakazu Iwasaki、Yoshihiro Kobayashi、Ji Ping Li、Hiroyuki Matsuzaka、Youichi Ishii、Masanobu Hidai

  DOI：10.1021/jo00005a046

  日期：1991.3

  Acetoxybenzofurans, acetoxybenzothiophenes, acetoxyindoles, and acetoxycarbazoles were obtained in high yields by cyclocarbonylation of 3-furyl-, 3-thienyl-, 3-pyrrolyl-, and 3-indolylallyl acetates, respectively, in the presence of Ac2O, NEt3, and a catalytic amount of PdCl2(PPh3)2 at 130-170-degrees-C under 50-70 atm of CO. 3-(3-Furyl)allyl and 3-(3-thienyl)allyl acetates cyclized selectively at the 2-position of the heterocyclic nucleus to give 7-acetoxybenzofuran and 7-acetoxybenzothiophene, respectively. The synthetic utility of the reaction was demonstrated by the synthesis of cannabifuran from isothymol.