1,2,3,4-tetrahydronaphthalen-2-yl butyrate

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2,3,4-tetrahydronaphthalen-2-yl butyrate
• 英文别名: butyric acid-(1,2,3,4-tetrahydro-[2]naphthyl ester)；Buttersaeure-(1,2,3,4-tetrahydro-[2]naphthylester)；(+/-)-2-Butyryloxy-tetralin；(+/-)-(1.2.3.4-Tetrahydro-naphthyl-(2))-butyrat；(+/-)-2-Butyryloxy-1.2.3.4-tetrahydro-naphthalin；1,2,3,4-Tetrahydronaphthalen-2-yl butanoate
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: SKWRQMBTIMSKGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydronaphthalen-2-yl butyrate 在 水 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 (R)-(+)-1,2,3,4-tetrahydro-2-naphthol
  参考文献：
  名称：

  Enzymatic resolution of 5-hydroxy- and 8-hydroxy-2-tetralols using immobilized lipases

  摘要：

  (R)-2-Tetralol (R)-2a, (R)-5-hydroxy-2-tetralol (R)-2b and (R)-8-hydroxy-2-tetralol (R)-2c, which are key intermediates in the synthesis of pharmacologically active 2-aminotetralins 3, were prepared in moderate to very high enantiomeric excess (up to 99% ee) by enzymatic resolution of the corresponding racemic butyrates rac-1a, rac-1b and rac-1c, respectively, using lipases immobilized on octyl agarose. This methodology is an alternative to the microbial reduction of 2-tetralones. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.011
• 作为产物：
  描述：

  溴甲苯 在 palladium diacetate 、 Selectfluor 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.0h， 生成 1,2,3,4-tetrahydronaphthalen-2-yl butyrate
  参考文献：
  名称：

  Monocarboxylation and Intramolecular Coupling of Butenylated Arenes via Palladium-Catalyzed C–H Activation Process

  摘要：

  A novel and practical reaction for the direct intramolecular oxidative coupling of butenylated arenes is reported. With the catalysis of Pd(OAc)(2), reactions of various butenylated arenes and carboxylic acids with Selectfluor reagent in CH3CN solution afforded the corresponding monocarboxylation/cyclization products in good yields under mild conditions. This research demonstrated an economic method with the synthesis of 2-tetralyl carboxylic esters, a valuable class of bioactive compounds.

  DOI：

  10.1021/acs.orglett.5b00376

文献信息

• Monocarboxylation and Intramolecular Coupling of Butenylated Arenes via Palladium-Catalyzed C–H Activation Process
  作者：Rui Liu、Ze-Hai Lu、Xiao-Hui Hu、Jun-Li Li、Xian-Jin Yang

  DOI：10.1021/acs.orglett.5b00376

  日期：2015.3.20

  A novel and practical reaction for the direct intramolecular oxidative coupling of butenylated arenes is reported. With the catalysis of Pd(OAc)(2), reactions of various butenylated arenes and carboxylic acids with Selectfluor reagent in CH3CN solution afforded the corresponding monocarboxylation/cyclization products in good yields under mild conditions. This research demonstrated an economic method with the synthesis of 2-tetralyl carboxylic esters, a valuable class of bioactive compounds.
• Enzymatic resolution of 5-hydroxy- and 8-hydroxy-2-tetralols using immobilized lipases
  作者：Paolo Bonomi、Paola Cairoli、Daniela Ubiali、Carlo F. Morelli、Marco Filice、Ines Nieto、Massimo Pregnolato、Paolo Manitto、Marco Terreni、Giovanna Speranza

  DOI：10.1016/j.tetasy.2009.02.011

  日期：2009.3

  (R)-2-Tetralol (R)-2a, (R)-5-hydroxy-2-tetralol (R)-2b and (R)-8-hydroxy-2-tetralol (R)-2c, which are key intermediates in the synthesis of pharmacologically active 2-aminotetralins 3, were prepared in moderate to very high enantiomeric excess (up to 99% ee) by enzymatic resolution of the corresponding racemic butyrates rac-1a, rac-1b and rac-1c, respectively, using lipases immobilized on octyl agarose. This methodology is an alternative to the microbial reduction of 2-tetralones. (c) 2009 Elsevier Ltd. All rights reserved.