β-(1-Hydroxy-3-methylbut-3-enyl)indole | 122284-51-9

• 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: β-(1-Hydroxy-3-methylbut-3-enyl)indole
• 英文别名: 1-(1H-indol-3-yl)-3-methylbut-3-en-1-ol
• CAS: 122284-51-9
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: WCJQJCKIAWGUHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  β-(1-Hydroxy-3-methylbut-3-enyl)indole 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以62%的产率得到3-Isoprenylindole
  参考文献：
  名称：

  Sheu, Jyh-Horng; Chen, Yua-Kuang; Chung, Huey-Fen, Journal of the Chemical Society. Perkin transactions I, 1998, # 12, p. 1959 - 1965

  摘要：

  DOI：
• 作为产物：
  描述：

  3-吲哚甲醛 、 3-氯-2-甲基丙烯 在 碘 magnesium 作用下， 生成 β-(1-Hydroxy-3-methylbut-3-enyl)indole
  参考文献：
  名称：

  Efficient syntheses of yuehchukene and .beta.-(dehydroprenyl)indole

  摘要：

  Yuehchukene (1) has been synthesized by one-step transformations of both alcohols (E)-beta-(3-hydroxy-3-methylbutenyl)indole (3) and beta-(1-hydroxy-3-methylbut-3-enyl)indole (4) under various reaction conditions. Alcohol 3 can be prepared efficiently from indole-3-carboxaldehyde (8) via a two-step reaction sequence. Alcohol 4, an isomer of 3, can be obtained from the same starting materials 8 in only one step. Alcohol 4 can be converted directly into beta-(dehydroprenyl)indole (2) in high yield under mild conditions via a base-induced dehydration. However, alcohol 3 does not give diene 2 under the same reaction conditions. Since diene 2 has been used as the key intermediate for the syntheses of yuehchukene (1), analogues of 1, and a cytotoxic compound, murrapanine (7), our present work also completes formal total syntheses of these bioactive compounds.

  DOI：

  10.1021/jo00073a044

文献信息

• Synthesis of Yuehchukene Analogues, Murrapanine and Normurrapanine Utylizing Thermal Reaction of b-(1-Hydroxybutenyl)indoles under Neutral Reaction Conditions
  作者：Jyh-Horng Sheu、Yua-Kuang Chen、Huey-Fen Chung、Ping-Jyun Sung、Song-Fong Lin

  DOI：10.3987/com-96-7507

  日期：——

  beta-(1-Hydroxybutenyl)indoles, which were prepared in high yields from indole-3-carboxaldehyde, could be converted into yuehchukene analogues(8a, b) murrapanine (9a) and normurrapanine (9b) in one step under thermal-induced reaction conditions in neutral solution of ethylene glycol and water. beta-(1-Hydroxybutenyl)indoles are supposed to be dehydrated to 1-(beta-indolyl)-1,3-butadienes which react further to yuehchukene analogues via a Diels-Alder pathway. Murrapanine and normurrapanine showed a cytotoxicity toward KB cells.