(3-甲基-4-苯基丁烷-2-基)乙酸酯 | 34362-37-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (3-甲基-4-苯基丁烷-2-基)乙酸酯
• 英文名称: acetic acid-(1,2-dimethyl-3-phenyl-propyl ester)
• 英文别名: Opt.-inakt. 3-Acetoxy-2-methyl-1-phenyl-butan；Essigsaeure-(1,2-dimethyl-3-phenyl-propylester)；(1.2-Dimethyl-3-phenyl-propyl)-acetat；(2-methyl-3-acetoxybutyl)benzene；1,2-Dimethyl-3-phenylpropyl acetate；(3-methyl-4-phenylbutan-2-yl) acetate
• CAS: 34362-37-3
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: XAFAINACZOLWGU-UHFFFAOYSA-N

物化性质

• 沸点：
  285.9±19.0 °C(Predicted)
• 密度：
  0.986±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2915390090

反应信息

• 作为反应物：
  描述：

  (3-甲基-4-苯基丁烷-2-基)乙酸酯 生成 4-(2-methyl-3-acetoxybutyl)phenyl methyl ketone
  参考文献：
  名称：

  MIURA, TAKATSUGU;TAKEHSIMA, KEHNDZYUN;KODAMA, TAKUYA;IMAMURA, MASASI;XONK+

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯基重氮甲烷 在 4-二甲氨基吡啶 、 sodium carbonate 作用下， 以 乙酸乙酯 为溶剂， 生成 (3-甲基-4-苯基丁烷-2-基)乙酸酯
  参考文献：
  名称：

  Enantiopreference of Lipase from Pseudomonas cepacia toward Primary Alcohols

  摘要：

  We propose an empirical rule that predicts which enantiomer of a primary alcohol reacts faster in reactions catalyzed by lipase from Pseudomonas cepacia (PCL). This rule, based on the size of the substituents at the stereocenter, shows an 89% reliability (correct for 54 of 61 examples). This rule is not reliable for primary alcohols that have an oxygen atom attached to the stereocenter; we excluded these alcohols from the tally above. Surprisingly, the sense of enantiopreference of PCL toward primary alcohols is opposite to its enantiopreference toward secondary alcohols. That is, the OH of secondary alcohols and the CH2OH of primary alcohols point in opposite directions. We suggest, however, that this opposite orientation does not imply a different position of the substituents in the active site of the lipase. Instead, PCL accommodates the extra CH2 in primary alcohols as a kink between the stereocenter and the oxygen which allows a similar position of the alcohol oxygen in both. We tried to increase the enantioselectivity of PCL toward primary alcohols by increasing the difference in the size of the substituents but did not find a consistent increase in enantioselectivity. We suggest that high enantioselectivity toward primary alcohols requires not only a significant difference in the size of the substituents, but also control of the conformation along the C(1)-C(2) bond.

  DOI：

  10.1021/jo00126a056

文献信息

• Alkanoic acid, process for its production and method of use thereof
  申请人：Toyama Chemical Company Limited

  公开号：US04092350A1

  公开（公告）日：1978-05-30

  A novel 2-[4-(3-oxo- or hydroxy-alkyl)phenyl]alkanoic acid and a non-toxic salt thereof. These compounds are useful for treating symptoms of inflammation and pain in mammals including man. This disclosure relates to such compounds, a process for producing the same, a pharmaceutical composition containing such a compound, and a method for treating symptoms of inflammation and pain.

  一种新型的2-[4-(3-氧化或羟基-烷基)苯基]脂肪酸及其无毒盐。这些化合物可用于治疗哺乳动物，包括人类的炎症和疼痛症状。本发明涉及这些化合物，其制备方法，含有这种化合物的药物组合物，以及治疗炎症和疼痛症状的方法。
• Colonge; Pichat, Bulletin de la Societe Chimique de France, 1949, p. 177,183
  作者：Colonge、Pichat

  DOI：——

  日期：——
• MIURA, TAKATSUGU;TAKEHSIMA, KEHNDZYUN;KODAMA, TAKUYA;IMAMURA, MASASI;XONK+
  作者：MIURA, TAKATSUGU、TAKEHSIMA, KEHNDZYUN、KODAMA, TAKUYA、IMAMURA, MASASI、XONK+

  DOI：——

  日期：——
• US4092350A
  申请人：——

  公开号：US4092350A

  公开（公告）日：1978-05-30
• Enantiopreference of Lipase from Pseudomonas cepacia toward Primary Alcohols
  作者：Alexandra N. E. Weissfloch、Romas J. Kazlauskas

  DOI：10.1021/jo00126a056

  日期：1995.10

  We propose an empirical rule that predicts which enantiomer of a primary alcohol reacts faster in reactions catalyzed by lipase from Pseudomonas cepacia (PCL). This rule, based on the size of the substituents at the stereocenter, shows an 89% reliability (correct for 54 of 61 examples). This rule is not reliable for primary alcohols that have an oxygen atom attached to the stereocenter; we excluded these alcohols from the tally above. Surprisingly, the sense of enantiopreference of PCL toward primary alcohols is opposite to its enantiopreference toward secondary alcohols. That is, the OH of secondary alcohols and the CH2OH of primary alcohols point in opposite directions. We suggest, however, that this opposite orientation does not imply a different position of the substituents in the active site of the lipase. Instead, PCL accommodates the extra CH2 in primary alcohols as a kink between the stereocenter and the oxygen which allows a similar position of the alcohol oxygen in both. We tried to increase the enantioselectivity of PCL toward primary alcohols by increasing the difference in the size of the substituents but did not find a consistent increase in enantioselectivity. We suggest that high enantioselectivity toward primary alcohols requires not only a significant difference in the size of the substituents, but also control of the conformation along the C(1)-C(2) bond.