dimethyl 2-(tert-butyldimethylsilyloxy)methylcyclopropane-1,1-dicarboxylate | 426820-61-3

• 英文名称: dimethyl 2-(tert-butyldimethylsilyloxy)methylcyclopropane-1,1-dicarboxylate
• CAS: 426820-61-3
• 化学式: C₁₄H₂₆O₅Si
• 分子量: 302.443
• InChiKey: ODLCUGIFCNKYTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(tert-butyldimethylsilyloxy)methylcyclopropane-1,1-dicarboxylate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Synthesis of Labeled 1-Amino-2-methylenecyclopropane- 1-carboxylic Acid, an Inactivator of 1-Aminocyclopropane-1-carboxylate Deaminase

  摘要：

  1-Amino-2-methylenecyclopropane-1-carboxylic acid (2-methylene-ACC) is an irreversible inhibitor for a bacterial enzyme, 1-aminocyclopropane-1-carboxylate (ACC) deaminase, which catalyzes the conversion of ACC to alpha-ketobutyrate and ammonia. The inactivation has been proposed to proceed with the ring scission induced by an addition of an enzyme nucleophile, resulting in the formation of a reactive turnover product that then traps an active-site residue. To gain further insight into this unique enzymatic reaction, the tritiated 2-methylene-ACC was prepared and incubated with ACC deaminase to locate and identify the entrapped amino acid residue. The synthesis of this radiolabeled compound and the results of its incubation with ACC deaminase are reported in this paper.

  DOI：

  10.1021/jo010994r
• 作为产物：
  描述：

  2-叠氮丙二酸二甲酯 、 叔丁基二甲基烯丙基硅醚 在 dirhodium tetraacetate 作用下， 反应 2.0h， 以78%的产率得到dimethyl 2-(tert-butyldimethylsilyloxy)methylcyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  Synthesis of Labeled 1-Amino-2-methylenecyclopropane- 1-carboxylic Acid, an Inactivator of 1-Aminocyclopropane-1-carboxylate Deaminase

  摘要：

  1-Amino-2-methylenecyclopropane-1-carboxylic acid (2-methylene-ACC) is an irreversible inhibitor for a bacterial enzyme, 1-aminocyclopropane-1-carboxylate (ACC) deaminase, which catalyzes the conversion of ACC to alpha-ketobutyrate and ammonia. The inactivation has been proposed to proceed with the ring scission induced by an addition of an enzyme nucleophile, resulting in the formation of a reactive turnover product that then traps an active-site residue. To gain further insight into this unique enzymatic reaction, the tritiated 2-methylene-ACC was prepared and incubated with ACC deaminase to locate and identify the entrapped amino acid residue. The synthesis of this radiolabeled compound and the results of its incubation with ACC deaminase are reported in this paper.

  DOI：

  10.1021/jo010994r