4-(4-Hydroxymethyl-3,3-dimethyl-2-oxo-pyrrolidin-1-yl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester | 910790-00-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(4-Hydroxymethyl-3,3-dimethyl-2-oxo-pyrrolidin-1-yl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester
• CAS: 910790-00-0
• 化学式: C₁₇H₂₇NO₄
• 分子量: 309.406
• InChiKey: SQRLHVPEEAZYJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.73
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(4-Hydroxymethyl-3,3-dimethyl-2-oxo-pyrrolidin-1-yl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester 在 N,N-二甲基丙烯基脲 、 potassium trimethylsilonate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 4-[4-(5-Cyano-pyridin-2-yloxymethyl)-3,3-dimethyl-2-oxo-pyrrolidin-1-yl]-bicyclo[2.2.2]octane-1-carboxylic acid amide
  参考文献：
  名称：

  Discovery of orally active butyrolactam 11β-HSD1 inhibitors

  摘要：

  A series of metabolically stable butyrolactam 11 beta-HSD1 inhibitors have been synthesized and biologically evaluated. These compounds exhibit excellent HSD1 potency and HSD2 selectivity, pharmacokinetic, and pharmacodynamic profiles. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.034
• 作为产物：
  描述：

  4-(tert-butyl-diphenyl-silanyloxy)-3-formyl-2,2-dimethyl-butyric acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 4-(4-Hydroxymethyl-3,3-dimethyl-2-oxo-pyrrolidin-1-yl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Discovery of orally active butyrolactam 11β-HSD1 inhibitors

  摘要：

  A series of metabolically stable butyrolactam 11 beta-HSD1 inhibitors have been synthesized and biologically evaluated. These compounds exhibit excellent HSD1 potency and HSD2 selectivity, pharmacokinetic, and pharmacodynamic profiles. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.034

文献信息

• A Highly Efficient Synthesis of Potent and Selective Butyrolactam Inhibitors of 11β-Hsd1
  作者：Vince S. C. Yeh、Ravi Kurukulasuriya、Francis A. Kerdesky

  DOI：10.1021/ol061429j

  日期：2006.8.1

  A convergent synthesis of structurally novel butyrolactam 11 beta-HSD1 inhibitors is described. The approach features an efficient Ireland-Claisen reaction to construct a highly substituted aldehyde building block which is converted to a lactam via a tandem reductive amination/cyclization sequence. The generality of the synthetic sequence is demonstrated during the preparation of two additional potent 11 beta-HSD1 inhibitors.