4-(tert-butyl-diphenyl-silanyloxy)-3-formyl-2,2-dimethyl-butyric acid methyl ester | 910789-89-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-(tert-butyl-diphenyl-silanyloxy)-3-formyl-2,2-dimethyl-butyric acid methyl ester
• 英文别名: 4-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-3-formyl-2,2-dimethylbutanoic acid methyl ester；methyl 3-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-4-oxobutanoate
• CAS: 910789-89-8
• 化学式: C₂₄H₃₂O₄Si
• 分子量: 412.601
• InChiKey: BFEYSRQQUDBOEC-UHFFFAOYSA-N

物化性质

• 沸点：
  473.7±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(tert-butyl-diphenyl-silanyloxy)-3-formyl-2,2-dimethyl-butyric acid methyl ester 在 N,N-二甲基丙烯基脲 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,3S,5R,9S)-9-[4-(5-Cyano-pyridin-2-yloxymethyl)-3,3-dimethyl-2-oxo-pyrrolidin-1-yl]-bicyclo[3.3.1]nonane-3-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
• 作为产物：
  描述：

  (Z)-4-((tert-butyldiphenylsilyl)oxy)but-2-en-1-ol 在 4-二甲氨基吡啶 、 双(三甲基硅烷基)氨基钾 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 22.0h， 生成 4-(tert-butyl-diphenyl-silanyloxy)-3-formyl-2,2-dimethyl-butyric acid methyl ester
  参考文献：
  名称：

  A Highly Efficient Synthesis of Potent and Selective Butyrolactam Inhibitors of 11β-Hsd1

  摘要：

  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.

  DOI：

  10.1021/ol061429j

文献信息

• WO2007/118185
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• Discovery of orally active butyrolactam 11β-HSD1 inhibitors
  作者：Vince S.C. Yeh、Ravi Kurukulasuriya、Steven Fung、Katina Monzon、William Chiou、Jiahong Wang、Deanne Stolarik、Hovis Imade、Robin Shapiro、Victoria Knourek-Segel、Eugene Bush、Denise Wilcox、Phong T. Nguyen、Michael Brune、Peer Jacobson、J.T. Link

  DOI：10.1016/j.bmcl.2006.08.034

  日期：2006.11

  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.