(Z)-6-(1-methyl-1H-indol-3-yl)hex-3-en-1-ol | 1424137-73-4

• 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: (Z)-6-(1-methyl-1H-indol-3-yl)hex-3-en-1-ol
• 英文别名: (Z)-6-(1-methylindol-3-yl)hex-3-en-1-ol
• CAS: 1424137-73-4
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: LZBRYKUTVRXSDW-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-6-(1-methyl-1H-indol-3-yl)hex-3-en-1-ol 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 4-(4-bromophenyl)-11-methyl-1,2,4,4α,5,6,11,11b-octahydrothiopyran[4,3-α]carbazole
  参考文献：
  名称：

  Novel protocol for the synthesis of octahydropyrano- and thiopyrano[4,3-a]carbazole derivatives via Prins/Friedel–Crafts cyclization

  摘要：

  A novel Prins/Friedel-Crafts cyclization of (Z)-6-(1-methyl-1H-indol-3-yl)hex-3-en-1-ol with aldehydes has been achieved using a catalytic amount of BF3 center dot OEt2 under mild reaction conditions to produce the corresponding octahydropyrano[4,3-a]carbazole derivatives in good yields with high diastereoselectivity. The cross-coupling of (Z)-6-(1-methyl-1H-indo1-3-y1)hex-3-ene-1-thiol with aldehydes affords the corresponding octahydrothiopyrano[4,3-a]carbazole derivatives under similar conditions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.113
• 作为产物：
  描述：

  (Z)-3-(6-(benzyloxy)hex-3-en-1-yl)-1-methyl-1H-indole 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以80%的产率得到(Z)-6-(1-methyl-1H-indol-3-yl)hex-3-en-1-ol
  参考文献：
  名称：

  Novel protocol for the synthesis of octahydropyrano- and thiopyrano[4,3-a]carbazole derivatives via Prins/Friedel–Crafts cyclization

  摘要：

  A novel Prins/Friedel-Crafts cyclization of (Z)-6-(1-methyl-1H-indol-3-yl)hex-3-en-1-ol with aldehydes has been achieved using a catalytic amount of BF3 center dot OEt2 under mild reaction conditions to produce the corresponding octahydropyrano[4,3-a]carbazole derivatives in good yields with high diastereoselectivity. The cross-coupling of (Z)-6-(1-methyl-1H-indo1-3-y1)hex-3-ene-1-thiol with aldehydes affords the corresponding octahydrothiopyrano[4,3-a]carbazole derivatives under similar conditions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.113

文献信息

• Novel protocol for the synthesis of octahydropyrano- and thiopyrano[4,3-a]carbazole derivatives via Prins/Friedel–Crafts cyclization
  作者：B.V. Subba Reddy、P. Sivaramakrishna Reddy、J.S. Yadav、B. Sridhar

  DOI：10.1016/j.tetlet.2012.12.113

  日期：2013.3

  A novel Prins/Friedel-Crafts cyclization of (Z)-6-(1-methyl-1H-indol-3-yl)hex-3-en-1-ol with aldehydes has been achieved using a catalytic amount of BF3 center dot OEt2 under mild reaction conditions to produce the corresponding octahydropyrano[4,3-a]carbazole derivatives in good yields with high diastereoselectivity. The cross-coupling of (Z)-6-(1-methyl-1H-indo1-3-y1)hex-3-ene-1-thiol with aldehydes affords the corresponding octahydrothiopyrano[4,3-a]carbazole derivatives under similar conditions. (C) 2013 Elsevier Ltd. All rights reserved.