1-acetyl-2,3-dihydro-2,2'-bisindole | 172950-81-1

• 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-acetyl-2,3-dihydro-2,2'-bisindole
• 英文别名: 1-acetyl-2,3-dihydro-2,2'biindolyl；1-[2-(1H-indol-2-yl)-2,3-dihydroindol-1-yl]ethanone
• CAS: 172950-81-1
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: XHSHMZMGZSHOON-UHFFFAOYSA-N

物化性质

• 沸点：
  544.8±45.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-acetyl-2,3-dihydro-2,2'-bisindole 在 sodium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(2,3-Dihydro-1'H-[2,2']biindolyl-1-yl)-propionitrile
  参考文献：
  名称：

  Short Step Syntheses of Indolo[2,3-a]carbazoles Carrying an Alkyl, Allyl, or a Glycosyl Group at the 11-Position and a Novel 6,7-Dihydro-13H-cyclopentano[mn]indolo[3,2-c]acridine Derivative

  摘要：

  Novel 1-alkyl-, 1-allyl-, and 1-beta-glycosyl-2,2'-biindolyls are prepared. Their Diels-Alder reaction produced 11-alkyl-, 11-allyl-, and 11-beta-glycosylindolo[2,3-a]carbazoles. Formation of a novel 6,7-dihydro-13H-cyclopentano[mn]indolo[3,2-c]acridine derivative is also reported.

  DOI：

  10.3987/com-01-s(k)40
• 作为产物：
  描述：

  1H,1H'-2,2'-Biindolylidene-3,3'-dione 在 乙酸酐 、 锌 作用下， 以 溶剂黄146 为溶剂， 反应 8.0h， 以18%的产率得到3-acetoxy-2,2′-bisindole
  参考文献：
  名称：

  Reduction of Indigo: Simple Syntheses of 3-Acetoxy-, 1-Acetyl-2,3-dihydro-, 3-Acetoxy-3'-acetyl-, 3-Acetoxy-1,3'-diacetyl-2,2'-bisindoles, and 2,2'-Bisindole

  摘要：

  Indigo was converted to 2,2'-bisindole by the direct reduction with zinc in acetic acid and acetic anhydride under argon or hydrogen atmosphere. Reduction with tin and iron afforded 3-acetoxy-2,2'-bisindole predominantly. Useful building blocks such as 1-acetyl-2,3-dihydro-, 3-acetoxy-3'-acetyl-, and 3-acetoxy-1,3'-diacetyl-2,2'-bisindoles were also produced depending on metal and reaction conditions.

  DOI：

  10.3987/com-95-s4

文献信息

• Simple Synthesis of 2,2'-Bisindole from Indigo and Its Application for the Syntheses of Indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)dione and -5-(6H)one Derivatives
  作者：Masanori Somei、Hiroyuki Hayashi、Tohru Izumi、Shinobu Ohmoto

  DOI：10.3987/com-95-7192

  日期：——

  Indigo was converted to 2,2'-bisindole, from which 6-substituted indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)dione and -5-(6H)one derivatives were prepared in short steps. Bromination of 6-methylindolo[2,3-a]pyrrolo[3,4-c]carbazole5,7-(6H)dione is also reported.
• Short Step Syntheses of Indolo[2,3-a]carbazoles Carrying an Alkyl, Allyl, or a Glycosyl Group at the 11-Position and a Novel 6,7-Dihydro-13H-cyclopentano[mn]indolo[3,2-c]acridine Derivative
  作者：Masanori Somei、Fumio Yamada、Jun Kato、Yoshiaki Suzuki、Yoshinori Ueda

  DOI：10.3987/com-01-s(k)40

  日期：——

  Novel 1-alkyl-, 1-allyl-, and 1-beta-glycosyl-2,2'-biindolyls are prepared. Their Diels-Alder reaction produced 11-alkyl-, 11-allyl-, and 11-beta-glycosylindolo[2,3-a]carbazoles. Formation of a novel 6,7-dihydro-13H-cyclopentano[mn]indolo[3,2-c]acridine derivative is also reported.
• Reduction of Indigo: Simple Syntheses of 3-Acetoxy-, 1-Acetyl-2,3-dihydro-, 3-Acetoxy-3'-acetyl-, 3-Acetoxy-1,3'-diacetyl-2,2'-bisindoles, and 2,2'-Bisindole
  作者：Masanori Somei、Hiroyuki Hayashi、Shinobu Ohmoto

  DOI：10.3987/com-95-s4

  日期：——

  Indigo was converted to 2,2'-bisindole by the direct reduction with zinc in acetic acid and acetic anhydride under argon or hydrogen atmosphere. Reduction with tin and iron afforded 3-acetoxy-2,2'-bisindole predominantly. Useful building blocks such as 1-acetyl-2,3-dihydro-, 3-acetoxy-3'-acetyl-, and 3-acetoxy-1,3'-diacetyl-2,2'-bisindoles were also produced depending on metal and reaction conditions.