methyl [3-hydroxy-1-(3-methyl-2-buten-1-yl)-2-oxo-2,3-dihydroindol-3-yl]acetamide | 885117-73-7

• 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: methyl [3-hydroxy-1-(3-methyl-2-buten-1-yl)-2-oxo-2,3-dihydroindol-3-yl]acetamide
• CAS: 885117-73-7
• 化学式: C₁₆H₂₀N₂O₃
• 分子量: 288.346
• InChiKey: LKAKTHBRAIDOFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  69.64
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl [3-hydroxy-1-(3-methyl-2-buten-1-yl)-2-oxo-2,3-dihydroindol-3-yl]acetamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以55%的产率得到3a-hydroxy-1-methyl-8-(3-methyl-2-buten-1-yl)-1,2,3,3a,8a-hexahydropyrrolo[2,3-b]indole
  参考文献：
  名称：

  Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural products

  摘要：

  This work describes a general protocol for the oxidation of indole and oxindole derivatives with dimethyldioxirane to give 3-hydroxyoxindoles present in many natural products. This strategy allowed us to synthesize the natural product 1, to carry out the first total synthesis of 4, a formal total synthesis of donaxaridine (5) and to achieve the synthesis of pyrroloindoline 8, a debromo analogue of the natural product flustraminol B (7). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.036
• 作为产物：
  描述：

  甲基吲哚-3-乙酸盐 在 碳酸氢钠 Oxone 、 disodium ethylenediaminetetraacetic acid 、 sodium hydride 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 丙酮 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 49.25h， 生成 methyl [3-hydroxy-1-(3-methyl-2-buten-1-yl)-2-oxo-2,3-dihydroindol-3-yl]acetamide
  参考文献：
  名称：

  Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural products

  摘要：

  This work describes a general protocol for the oxidation of indole and oxindole derivatives with dimethyldioxirane to give 3-hydroxyoxindoles present in many natural products. This strategy allowed us to synthesize the natural product 1, to carry out the first total synthesis of 4, a formal total synthesis of donaxaridine (5) and to achieve the synthesis of pyrroloindoline 8, a debromo analogue of the natural product flustraminol B (7). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.036

文献信息

• Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural products
  作者：Oscar R. Suárez-Castillo、Maricruz Sánchez-Zavala、Myriam Meléndez-Rodríguez、Luis E. Castelán-Duarte、Martha S. Morales-Ríos、Pedro Joseph-Nathan

  DOI：10.1016/j.tet.2006.01.036

  日期：2006.3

  This work describes a general protocol for the oxidation of indole and oxindole derivatives with dimethyldioxirane to give 3-hydroxyoxindoles present in many natural products. This strategy allowed us to synthesize the natural product 1, to carry out the first total synthesis of 4, a formal total synthesis of donaxaridine (5) and to achieve the synthesis of pyrroloindoline 8, a debromo analogue of the natural product flustraminol B (7). (c) 2006 Elsevier Ltd. All rights reserved.