Optical Resolution and Determination of Absolute Configurations of α-Isopropyl-4-substituted Phenylacetic Acids and Insecticidal Activities of Their 5-Benzyl-3-furylmethyl Esters
Optical Resolution and Determination of Absolute Configurations of α-Isopropyl-4-substituted Phenylacetic Acids and Insecticidal Activities of Their 5-Benzyl-3-furylmethyl Esters
复制标题
α-异丙基-4-取代苯乙酸的光学拆分和绝对构型测定及其 5-苄基-3-呋喃基甲酯的杀虫活性
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发表时间：
1975
期刊：
影响因子：
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通讯作者：
H. Yoshioka
中科院分区：
文献类型：
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作者：
M. Miyakado;N. Ohno;Y. Okuno;M. Hirano;K. Fujimoto;H. Yoshioka
结合一类新杀虫剂--改性苯乙酸酯的公开，提出了六种新的光学活性α-异丙基-4-取代苯乙酸，其取代基分别为4-甲基、4-甲氧基、4-氟、4-氯、4-溴和3，用光学拆分法制备了4-亚甲二氧基，并与α-亚甲基二氧基进行了比较，确定了它们的绝对构型。异丙基苯乙酸衍生物，其绝对构型已知为（S）-（2）。（S）-（2）-酸与5-苄基-3-呋喃甲醇的酯对家蝇的毒性几乎是外消旋酯的两倍。通过GLC和NMR（用Eu-FOD）确定拆分的酸的光学纯度为（-）-甲酯。
In connection with disclosure of a new class of insecticides, the modified phenylacetates, six new optically active α-isopropy-4-substituted phenylacetic acids whose substituents are respectively 4-methyl,4-methoxy, 4-fluoro, 4-chloro, 4-bromo and 3,4-methylenedioxy group were prepared by optical resolution and their absolute configurations were determined by comparative ORD with α-isopropylphenylacetic acid derivatives whose absolute configuration is known as (S)-(²). Esters of the (S)-(²)-acids with 5-benzyl-3-furylmethanol were nearly twice toxic to Musca domestica than those of the racemic esters. Optical purities of the resolved acids were determined by GLC and NMR (with Eu-FOD) as (−)-methyl esters.