2-(5-溴-6-甲氧基萘-2-基)丙酸乙酯 | 866365-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-(5-溴-6-甲氧基萘-2-基)丙酸乙酯
• 英文名称: ethyl 2-(5-bromo-6-methoxynaphthalen-2-yl)propanoate
• 英文别名: 2-(5-Bromo-6-methoxy-naphthalen-2-yl)-propionic acid ethyl ester
• CAS: 866365-36-8
• 化学式: C₁₆H₁₇BrO₃
• 分子量: 337.213
• InChiKey: CGUNBWNUEDUGSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(5-溴-6-甲氧基萘-2-基)丙酸乙酯 在 Candida cylindraceae lipase 作用下， 以 phosphate buffer 为溶剂， 反应 105.0h， 生成 (S)-2-(5-Bromo-6-methoxy-naphthalen-2-yl)-propionic acid ethyl ester 、 (R)-2-(5-Bromo-6-methoxy-naphthalen-2-yl)-propionic acid ethyl ester 、 5-溴萘普生 、 (R)-5-溴萘普生
  参考文献：
  名称：

  Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates

  摘要：

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.009
• 作为产物：
  描述：

  rac-5-溴萘普生 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 2-(5-溴-6-甲氧基萘-2-基)丙酸乙酯
  参考文献：
  名称：

  Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates

  摘要：

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.009

文献信息

• Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates
  作者：Surrinder Koul、Jawahir Lal Koul、Budh Singh、Munish Kapoor、Rajinder Parshad、Kuldeep S. Manhas、Subhash C. Taneja、Ghulam N. Qazi

  DOI：10.1016/j.tetasy.2005.07.009

  日期：2005.8

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.