3-heptyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole | 403597-68-2

• 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: 3-heptyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole
• 英文别名: 4-(Benzenesulfonyl)-3-heptylfuro[3,4-b]indole
• CAS: 403597-68-2
• 化学式: C₂₃H₂₅NO₃S
• 分子量: 395.522
• InChiKey: WSQBBHPUNLZWIL-UHFFFAOYSA-N

物化性质

• 沸点：
  567.8±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-heptyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole 、 碘甲烷 在 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 4.0h， 以164 mg的产率得到1-methyl-3-heptyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole
  参考文献：
  名称：

  An Efficient Synthesis of 4-(Phenylsulfonyl)-4H-furo[3,4-b]indoles

  摘要：

  The fused heterocycle 4-(phenylsulfonyl)-4H-furo-[3,4-b]indole, which is an indole-2,3-quinodimethane synthetic analogue, is prepared in five steps from indole in 46% yield. A similar sequence is used to synthesize C-3 derivatives (3-methyl, 3-phenyl, and 3-heptyl). Thus, indole-3-carbaldehyde (1) is protected as the N-phenylsulfonyl derivative 2 and converted to the ethylene acetal 6. Lithiation at C-2 followed by treatment with an aldehyde affords the expected hydroxy acetals 7 and S. Exposure to acid effects cyclization to the furoindoles 5 and 9. Furthermore, C-1 lithiation of furo[3,4-b]indole 9c followed by treatment with methyl iodide affords disubstituted furo[3,4-b]indole 10.

  DOI：

  10.1021/jo010938q
• 作为产物：
  描述：

  1-(phenylsulfonyl)-3-formaldehyde ethylene glycol acetal 在 仲丁基锂 、 对苯二酚 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 22.0h， 生成 3-heptyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole
  参考文献：
  名称：

  An Efficient Synthesis of 4-(Phenylsulfonyl)-4H-furo[3,4-b]indoles

  摘要：

  The fused heterocycle 4-(phenylsulfonyl)-4H-furo-[3,4-b]indole, which is an indole-2,3-quinodimethane synthetic analogue, is prepared in five steps from indole in 46% yield. A similar sequence is used to synthesize C-3 derivatives (3-methyl, 3-phenyl, and 3-heptyl). Thus, indole-3-carbaldehyde (1) is protected as the N-phenylsulfonyl derivative 2 and converted to the ethylene acetal 6. Lithiation at C-2 followed by treatment with an aldehyde affords the expected hydroxy acetals 7 and S. Exposure to acid effects cyclization to the furoindoles 5 and 9. Furthermore, C-1 lithiation of furo[3,4-b]indole 9c followed by treatment with methyl iodide affords disubstituted furo[3,4-b]indole 10.

  DOI：

  10.1021/jo010938q

文献信息

• An Efficient Synthesis of 4-(Phenylsulfonyl)-4<i>H</i>-furo[3,4-<i>b</i>]indoles
  作者：Gordon W. Gribble、Jun Jiang、Yanbing Liu

  DOI：10.1021/jo010938q

  日期：2002.2.1

  The fused heterocycle 4-(phenylsulfonyl)-4H-furo-[3,4-b]indole, which is an indole-2,3-quinodimethane synthetic analogue, is prepared in five steps from indole in 46% yield. A similar sequence is used to synthesize C-3 derivatives (3-methyl, 3-phenyl, and 3-heptyl). Thus, indole-3-carbaldehyde (1) is protected as the N-phenylsulfonyl derivative 2 and converted to the ethylene acetal 6. Lithiation at C-2 followed by treatment with an aldehyde affords the expected hydroxy acetals 7 and S. Exposure to acid effects cyclization to the furoindoles 5 and 9. Furthermore, C-1 lithiation of furo[3,4-b]indole 9c followed by treatment with methyl iodide affords disubstituted furo[3,4-b]indole 10.