methyl (1-acetyl-2-oxo-2,3-dihydroindol-3-yl)acetate | 61936-94-5

• 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 (1-acetyl-2-oxo-2,3-dihydroindol-3-yl)acetate
• 英文别名: (1-acetyl-2-oxo-2,3-dihydro-indol-3-yl)-acetic acid methyl ester；methyl 2-(1-acetyl-2-oxo-3H-indol-3-yl)acetate
• CAS: 61936-94-5
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: HOZOHLKCOWOWRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (1-acetyl-2-oxo-2,3-dihydroindol-3-yl)acetate 在 碳酸氢钠 Oxone 、 disodium ethylenediaminetetraacetic acid 、 丙酮 作用下， 以 水 为溶剂， 反应 0.75h， 以69%的产率得到methyl (1-acetyl-3-hydroxy-2-oxo-2,3-dihydroindol-3-yl)acetate
  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：

  (2-氧代-2,3-二氢-1H-吲哚-3-基)-乙酸 在 吡啶 、 对甲苯磺酸 作用下， 反应 16.0h， 生成 methyl (1-acetyl-2-oxo-2,3-dihydroindol-3-yl)acetate
  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.