methyl α-(phenylmethyl)indole-3-acetate | 113975-70-5

• 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 α-(phenylmethyl)indole-3-acetate
• 英文别名: α-(phenylmethyl)-1H-indole-3-acetic acid, methyl ester；methyl α-benzylindole-3-acetate；Methyl alpha-Benzylindole-3-acetate；methyl 2-(1H-indol-3-yl)-3-phenylpropanoate
• CAS: 113975-70-5
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: CVTCKJXXNZBWAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl α-(phenylmethyl)indole-3-acetate 在 甲醇 、 sodium hydroxide 、 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 2.0h， 生成 右培美酸
  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-吲哚乙酸 在 硫酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 22.0h， 生成 methyl α-(phenylmethyl)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

• Substituted 1,3,4,9-tetrahydropyrano(3,4-B)indole-1-acetic acids
  申请人：American Home Products Corporation

  公开号：US04670462A1

  公开（公告）日：1987-06-02

  Indole derivatives characterized by having a 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid nucleus bearing a substituent in position 1 and 4. The nucleus may be optionally substituted at positions 5, 6, 7 and 8. The derivatives are useful anti-inflammatory and analgesic agents and methods for their preparation and use are also disclosed.

  具有1,3,4,9-四氢吡喃并[3,4-b]吲哚-1-乙酸核的吲哚衍生物，其在位置1和4带有取代基。该核在位置5、6、7和8处可选择性地被取代。这些衍生物是有用的抗炎和镇痛剂，并且还公开了它们的制备和使用方法。
• 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.

  用于生产具有有用的镇痛和抗炎活性的取代的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。
• KATZ, ALAN H.;DEMERSON, CHRISTOPHER A.;HUMBER, LESLIE G.
  作者：KATZ, ALAN H.、DEMERSON, CHRISTOPHER A.、HUMBER, LESLIE G.

  DOI：——

  日期：——
• SHAW, CHIA-CHENG;PELZ, KAREL
  作者：SHAW, CHIA-CHENG、PELZ, KAREL

  DOI：——

  日期：——