2-ethoxy-2-(2-naphthyl)ethanenitrile | 33224-80-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-ethoxy-2-(2-naphthyl)ethanenitrile
• 英文别名: 2-Ethoxy-2-(2-naphthyl)acetonitrile；2-ethoxy-2-naphthalen-2-ylacetonitrile
• CAS: 33224-80-5
• 化学式: C₁₄H₁₃NO
• 分子量: 211.263
• InChiKey: SERAXWXRCADJHK-UHFFFAOYSA-N

物化性质

• 熔点：
  53-54 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  339.6±30.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三甲基氰硅烷 、 2-Diethoxymethyl-naphthalene 在 三氟化硼乙醚 作用下， 生成 2-ethoxy-2-(2-naphthyl)ethanenitrile
  参考文献：
  名称：

  Design, synthesis and evaluation of novel P450 fluorescent probes bearing α-cyanoether

  摘要：

  Four chi-cyano-containing ethers based on 2-alkoxy-2-naphtyhlacetonitriles have been designed as a novel Structural class of cytochrome P450 fluorescent probes. Their syntheses, fluorescence properties and evaluation in the fluorogenic assay of cytochrome P450 monooxygenase are reported. After P450 enzymatic O-dealkylation, the cyanohydrin metabolite of the four new substrates rearranges to a fluorescent aromatic aldehyde with a larger Stokes shift. and tile new substrates exhibit higher specific activities than that of the commercial substrate 7-ethoxyresorufin (ER). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00953-5

文献信息

• Cyanohydrin ethers and esters as high-sensitivity enzyme substrates
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20030207344A1

  公开（公告）日：2003-11-06

  Ethers and esters of cyanohydrins that contain optically detectable moieties are highly effective for detecting, monitoring, and measuring the activity of enzymes that cause the cleavage of certain types of substrates. The cyanohydrins function as proaldehydes and proketones, spontaneously converting to aldehydes and ketones, respectively, which provide a large increase in optical detectability relative to both the starting esters and ethers and the cyanohydrins.
• US6528675B1
  申请人：——

  公开号：US6528675B1

  公开（公告）日：2003-03-04
• US6710200B2
  申请人：——

  公开号：US6710200B2

  公开（公告）日：2004-03-23
• [EN] CYANOHYDRIN ETHERS AND ESTERS AS HIGH-SENSITIVITY ENZYME SUBSTRATES<br/>[FR] ETHERS ET ESTERS DE CYANHYDRINE UTILISES COMME SUBSTRATS ENZYMATIQUES A FORTE SENSIBILITE
  申请人：UNIV CALIFORNIA

  公开号：WO2003104167A2

  公开（公告）日：2003-12-18

  Ethers and esters of cyanohydrins that contain optically detectable moieties are highly effective for detecting, monitoring, and measuring the activity of enzymes that cause the cleavage of certain types of substrates. The cyanohydrins function as proaldehydes and proketones, spontaneously converting to aldehydes and ketones, respectively, which provide a large increase in optical detectability relative to both the starting esters and ethers and the cyanohydrins.
• Design, synthesis and evaluation of novel P450 fluorescent probes bearing α-cyanoether
  作者：Rong Zhang、Kyung-Don Kang、Guomin Shan、Bruce D. Hammock

  DOI：10.1016/s0040-4039(03)00953-5

  日期：2003.6

  Four chi-cyano-containing ethers based on 2-alkoxy-2-naphtyhlacetonitriles have been designed as a novel Structural class of cytochrome P450 fluorescent probes. Their syntheses, fluorescence properties and evaluation in the fluorogenic assay of cytochrome P450 monooxygenase are reported. After P450 enzymatic O-dealkylation, the cyanohydrin metabolite of the four new substrates rearranges to a fluorescent aromatic aldehyde with a larger Stokes shift. and tile new substrates exhibit higher specific activities than that of the commercial substrate 7-ethoxyresorufin (ER). (C) 2003 Elsevier Science Ltd. All rights reserved.