9,10-dihydro-γ-oxo-2-phenanthrenebutanoic acid methyl ester | 39093-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 9,10-dihydro-γ-oxo-2-phenanthrenebutanoic acid methyl ester
• 英文别名: 4-(9,10-dihydro-[2]phenanthryl)-4-oxo-butyric acid methyl ester；4-(9,10-Dihydro-[2]phenanthryl)-4-oxo-buttersaeure-methylester；Methyl 4-(9,10-dihydrophenanthren-2-yl)-4-oxobutanoate
• CAS: 39093-16-8
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: MDPURQKPBOCIBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9,10-dihydro-γ-oxo-2-phenanthrenebutanoic acid methyl ester 在 palladium on activated charcoal 氢氧化钾 、 三氯化铝 、 PPA 、 氢气 作用下， 以 甲醇 为溶剂， 生成 3,8,9,10-Tetrahydro-2H-cyclopenta[a]chrysene-1,11-dione
  参考文献：
  名称：

  Synthesis of 2,3-dihydro-1H-cyclopenta [a]chrysene

  摘要：

  DOI：

  10.1021/jo00796a026
• 作为产物：
  描述：

  甲醇 、 4-(9,10-dihydro-[2]phenanthryl)-4-oxo-butyric acid 在 乙酰氯 作用下， 生成 9,10-dihydro-γ-oxo-2-phenanthrenebutanoic acid methyl ester
  参考文献：
  名称：

  A Method for the Synthesis of Certain 2-Substituted Phenanthrenes

  摘要：

  DOI：

  10.1021/ja01261a053

文献信息

• The Effect of 1,3-Diaryl-[1H]-pyrazole-4-acetamides on Glucose Utilization in ob/ob Mice
  作者：Gregory R. Bebernitz、Greg Argentieri、Beverly Battle、Christine Brennan、Bork Balkan、Bryan F. Burkey、Michele Eckhardt、Jiaping Gao、Prasad Kapa、Robert J. Strohschein、Herbert F. Schuster、Mary Wilson、David D. Xu

  DOI：10.1021/jm010032c

  日期：2001.8.1

  This article provides evidence of a new class of compounds, 1,3-diaryl-[1H]-pyrazole-4-acetamides, initially identified from their ability to increase glucose transport in an adipocyte and muscle cell line and ultimately demonstrating dramatic glucose lowering in ob/ob Mice, a diabetic animal model. The lead compound, 1, possessed some behavioral-like effects which were removed by structural variation during the course of this investigation. Specifically, 11 g (RI = meta-CF3, Ar2 = 4 ' biphenyl, R3 = diethylamide) illustrated the potency of this series with ED50 values for glucose lowering in ob/ob mice of 3.0 mg/kg/day. Concomitant with its effect on glucose lowering, 11g also caused a 50% reduction in insulin levels consistent with an agent that increases whole body insulin sensitivity. 11g showed favorable pharmacokinetic data with acceptable absorption, negligible metabolism, and good duration of action. 11g demonstrated no appreciable adipogenic effect through PPAR gamma agonism, a characteristic of the thiazolidinediones (TZD), and so represents a potentially new class of agents for the treatment of diabetes.
• Syntheses in the 1,2-Benzanthracene and Chrysene Series
  作者：Louis F. Fieser、William S. Johnson

  DOI：10.1021/ja01876a006

  日期：1939.7
• A Method for the Synthesis of Certain 2-Substituted Phenanthrenes
  作者：Byron Riegel、Marvin H. Gold、Michael A. Kubico

  DOI：10.1021/ja01261a053

  日期：1942.9
• Synthesis of 2,3-dihydro-1H-cyclopenta [a]chrysene
  作者：Augustine Silveira、Earl J. McWhorter

  DOI：10.1021/jo00796a026

  日期：1972.11