(E)-β-(3-Hydroxy-3-methylbutenyl)indole | 134051-29-9

• 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: (E)-β-(3-Hydroxy-3-methylbutenyl)indole
• 英文别名: β-(3-hydroxy-3-methylbutenyl)indole；(E)-4-(1H-indol-3-yl)-2-methylbut-3-en-2-ol
• CAS: 134051-29-9
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: NJUFMKZHZYUCKJ-BQYQJAHWSA-N

物化性质

• 沸点：
  406.4±25.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 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：

  (E)-β-(3-Hydroxy-3-methylbutenyl)indole 在 silica gel 、 三氟乙酸 作用下， 以 苯 为溶剂， 以25%的产率得到(+/-)-yuehchukene
  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
• 作为产物：
  描述：

  甲基锂 、 3-(1H-吲哚-3-基)-丙烯酸乙酯 以 四氢呋喃 为溶剂， 生成 (E)-β-(3-Hydroxy-3-methylbutenyl)indole
  参考文献：
  名称：

  有效的月桂树烯合成

  摘要：

  报导了三步合成yuehchukene 1，这是一种新型的二聚吲哚天然产物，它通过酸催化β-（3-羟基-3-甲基丁烯基）吲哚的反应具有抗植入活性。

  DOI：

  10.1016/s0040-4039(00)74483-2

文献信息

• An efficient synthesis of yuehchukene
  作者：Jyh-Horng Sheu、Yua-Kuang Chen、Yen-Long Vincent Hong

  DOI：10.1016/s0040-4039(00)74483-2

  日期：1991.2

  A three-step synthesis of yuehchukene 1, a novel dimeric indole natural product with anti-implantation activity via acid-catalyzed reaction of β-(3-hydroxy-3-methylbutenyl)indole is reported.

  报导了三步合成yuehchukene 1，这是一种新型的二聚吲哚天然产物，它通过酸催化β-（3-羟基-3-甲基丁烯基）吲哚的反应具有抗植入活性。
• Efficient syntheses of yuehchukene and .beta.-(dehydroprenyl)indole
  作者：Jyh Horng Sheu、Yua Kuang Chen、Yen Long Vincent Hong

  DOI：10.1021/jo00073a044

  日期：1993.10

  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.