methyl 2,3-dihydro-3-hydroxy-2-oxo-α-(phenylmethyl)-1H-indole-3-acetate | 113996-90-0

• 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 2,3-dihydro-3-hydroxy-2-oxo-α-(phenylmethyl)-1H-indole-3-acetate
• 英文别名: methyl 2,3-dihydro-3-hydroxy-α-(phenylmethyl)-2-oxo-1H-indole-3-acetate；Methyl 2,3-Dihydro-3-hydroxy-alpha-(phenylmethyl)-2-oxo-1H-indole-3-acetate；methyl 2-(3-hydroxy-2-oxo-1H-indol-3-yl)-3-phenylpropanoate
• CAS: 113996-90-0
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: YKWNCCMQOKQPHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,3-dihydro-3-hydroxy-2-oxo-α-(phenylmethyl)-1H-indole-3-acetate 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.5h， 生成 cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano<3,4-b>indole-1-acetic acid methyl ester
  参考文献：
  名称：

  Synthesis and analgesic activity of pemedolac [cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]indole-1-acetic acid]

  摘要：

  The synthesis of cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]indole -1-acetic acid, pemedolac (USAN), is described. This compound has been found to be a potent analgesic agent in primary screening. Pemedolac has been resolved and the active (+)-enantiomer assigned a 1S,4R absolute configuration on the basis of a crystallographic analysis of its (S)-(-)-borneol ester.

  DOI：

  10.1021/jm00401a029
• 作为产物：
  描述：

  3-苯丙酸甲酯 、 靛红 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 以21 g的产率得到methyl 2,3-dihydro-3-hydroxy-2-oxo-α-(phenylmethyl)-1H-indole-3-acetate
  参考文献：
  名称：

  Synthesis and analgesic activity of pemedolac [cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]indole-1-acetic acid]

  摘要：

  The synthesis of cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]indole -1-acetic acid, pemedolac (USAN), is described. This compound has been found to be a potent analgesic agent in primary screening. Pemedolac has been resolved and the active (+)-enantiomer assigned a 1S,4R absolute configuration on the basis of a crystallographic analysis of its (S)-(-)-borneol ester.

  DOI：

  10.1021/jm00401a029

文献信息

• Production of substituted 1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic
  申请人：American Home Products Corporation

  公开号：US04824961A1

  公开（公告）日：1989-04-25

  Process for the production of substituted 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acids having useful analgesic and anti-inflammatory activity.

  生产具有有用的镇痛和抗炎活性的取代1,3,4,9-四氢吡喃[3,4-b]吲哚-1-乙酸的过程。
• Production of substituted 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic
  申请人：American Home Products Corporation

  公开号：US04897493A1

  公开（公告）日：1990-01-30

  Process for the production of substituted 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acids having useful analgesic and anti-inflammatory activity.

  生产具有有用的镇痛和抗炎活性的取代1,3,4,9-四氢吡喃[3,4-b]吲哚-1-乙酸的过程。
• Substituted 1,3,4,9-tetrahydropyrano [3,4-b]indole-1-acetic acids
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0306149A2

  公开（公告）日：1989-03-08

  A novel process is described for the production of substituted 1,3,4,9-tetrahydropyrano[3,4-b-]­indole-1-acetic acids having useful analgesic and anti-inflammatory activity and having the formula (I) wherein R¹ is lower alkyl, R⁴ and R⁵ are hydrogen, lower alkyl or halogen and R² is hydrogen, 4-halogen 2,4-dihalo, 3-trifluoromethyl or 4-methoxy via the intermediate of formula

  本发明描述了一种生产取代的 1,3,4,9-四氢吡喃并[3,4-b-]吲哚-1-乙酸的新工艺，该工艺具有有用的镇痛和消炎活性，具有式 (I) 其中 R¹ 为低级烷基，R⁴ 和 R⁵ 为氢、低级烷基或卤素，R² 为氢、4-卤素 2,4-二卤素、3-三氟甲基或 4-甲氧基。
• Substituted 1,3,4,9-tetrahydropyrano[3,4-b]indole-l-acetic acids
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0337585A1

  公开（公告）日：1989-10-18

  A novel process is described for the production of substituted 1,3,4,9-tetrahydropyrano[3,4-b]­indole-1-acetic acids having useful analgesic and anti-inflammatory activity and having the formula (I) wherein R¹ is lower alkyl, R⁴ and R⁵ are hydrogen, lower alkyl or halogen and R² is hydrogen, 4-halogen 2,4 dihalo, 3-trifluoromethyl or 4-methoxy via the intermediate of formula which is prepared from an isatin derivative.

  本发明描述了一种生产取代的 1,3,4,9-四氢吡喃并[3,4-b]吲哚-1-乙酸的新工艺，该工艺具有有用的镇痛和消炎活性，具有式 (I) 其中 R¹ 为低级烷基，R⁴ 和 R⁵ 为氢、低级烷基或卤素，R² 为氢、4-卤素、2,4-二卤素、3-三氟甲基或 4-甲氧基。 由异atin 衍生物制备而成。
• J. Med. Chem. 1988, 31, 1244-1250
  作者：

  DOI：——

  日期：——