methyl (1-carbomethoxy-3-hydroxy-2-oxo-2,3-dihydroindol-3-yl)acetate | 885117-62-4

• 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: methyl (1-carbomethoxy-3-hydroxy-2-oxo-2,3-dihydroindol-3-yl)acetate
• 英文别名: methyl 3-hydroxy-3-(2-methoxy-2-oxoethyl)-2-oxoindoline-1-carboxylate；Methyl 3-hydroxy-3-(2-methoxy-2-oxoethyl)-2-oxoindole-1-carboxylate；methyl 3-hydroxy-3-(2-methoxy-2-oxoethyl)-2-oxoindole-1-carboxylate
• CAS: 885117-62-4
• 化学式: C₁₃H₁₃NO₆
• 分子量: 279.249
• InChiKey: IRAJRIPGJWSIRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (1-carbomethoxy-3-hydroxy-2-oxo-2,3-dihydroindol-3-yl)acetate 在 盐酸 、 silica gel 作用下， 以 甲醇 为溶剂， 反应 494.0h， 生成 methyl 4-(2-methoxy-2-oxoethyl)-2-oxo-2,4-dihydro-1H-benzo[d][1,3]oxazine-4-carboxylate
  参考文献：
  名称：

  Microwave-Assisted Synthesis of 3,1-Benzoxazin-2-ones from 3-Hydroxyoxindoles

  摘要：

  A general protocol for the synthesis of 3,1-benzoxazin-2-ones 18 from 3-hydroxyoxindoles 16 in a two steps sequence through phenylsuccinates or phenylpropionates 17 is described. Best reaction conditions for ring opening of 16 to succinates or propionates 17 were achieved using alcohol/silica gel, while cyclization of 17 to benzoxazinones 18 was easily done with HCl/alcohol. It was also found that 17 and 18 can be transesterified using HCl/alcohol. Most transformations were carried out by traditional heating and by microwave (MW) irradiation to accelerate reaction rates.

  DOI：

  10.3987/com-12-12472
• 作为产物：
  描述：

  甲基吲哚-3-乙酸盐 在 碳酸氢钠 Oxone 、 disodium ethylenediaminetetraacetic acid 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 丙酮 作用下， 以 水 为溶剂， 反应 29.0h， 生成 methyl (1-carbomethoxy-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

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.
• Microwave-Assisted Synthesis of 3,1-Benzoxazin-2-ones from 3-Hydroxyoxindoles
  作者：Oscar R. Suárez-Castillo、Claudia I. Bautista-Hernández、Maricruz Sánchez-Zavala、Myriam Meléndez-Rodríguez、Araceli Sierra-Zenteno、Martha S. Morales-Ríos、Pedro Joseph-Nathan

  DOI：10.3987/com-12-12472

  日期：——

  A general protocol for the synthesis of 3,1-benzoxazin-2-ones 18 from 3-hydroxyoxindoles 16 in a two steps sequence through phenylsuccinates or phenylpropionates 17 is described. Best reaction conditions for ring opening of 16 to succinates or propionates 17 were achieved using alcohol/silica gel, while cyclization of 17 to benzoxazinones 18 was easily done with HCl/alcohol. It was also found that 17 and 18 can be transesterified using HCl/alcohol. Most transformations were carried out by traditional heating and by microwave (MW) irradiation to accelerate reaction rates.