Theoretical Study of the Fragmentation of the β-Lactam Ring: Ozonolysis of 3-Methoxy-4-methyl-N-(ethylideneamino)-2-azetidinone

Diego Ardura; Tomas L. Sordo

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Theoretical Study of the Fragmentation of the β-Lactam Ring: Ozonolysis of 3-Methoxy-4-methyl-N-(ethylideneamino)-2-azetidinone

机译：β-内酰胺环断裂的理论研究：3-甲氧基-4-甲基-N-（亚乙基氨基）-2-氮杂环丁酮的臭氧分解

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A theoretical B3LYP/6-31+G~* study of the ozonolysis of 3-methoxy-4-methyl-N-(ethylideneamino)-2-azetidinone in dichloromethane at 195.15 K, and of the reduction of the corresponding ozonide with BH_4~- in EtOH/H_2O 1:1 at 273.15 K to yield methyl 1-propenyl ether, renders three reaction paths proceeding under the energy level corresponding to reactnats in accordance with the exceptionally mild reaction conditions experimentally found. Two of these paths lead to Z-methyl 1-propenyl ether with retention of stereochemistry whereas the other one gives E-methyl 1-propenyl ether. These theoretical results predict a high level of stereoselectivity in agreement with the experimental values obtained for the synthesis of vinyl ethers from the reaction of N-[(arylidene or alkylidene)amino]-2-azetidinones with ozone.

机译：B3LYP / 6-31 + G〜*的理论研究是在195.15 K下将3-甲氧基-4-甲基-N-（亚乙基氨基）-2-氮杂环丁酮在二氯甲烷中进行臭氧分解，以及用BH_4〜还原相应的臭氧化物。 -在273.15 K的EtOH / H_2O 1：1中生成甲基1-丙烯基醚，根据实验发现的异常温和的反应条件，在对应于反应物的能级下进行了三个反应路径的反应。这些路径中的两个导致形成立体化学保留的Z-甲基1-丙烯基醚，而另一个路径生成E-甲基1-丙烯基醚。这些理论结果预示了高水平的立体选择性，这与从N-[（亚芳基或亚烷基）氨基] -2-氮杂环丁酮与臭氧反应合成乙烯基醚获得的实验值一致。

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《The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory》 |2003年第47期|共6页
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Diego Ardura; Tomas L. Sordo;
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中图分类物理化学（理论化学）、化学物理学;
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1. Theoretical Study of the Fragmentation of the β-Lactam Ring: Ozonolysis of 3-Methoxy-4-methyl-N-(ethylideneamino)-2-azetidinone [J] . Diego Ardura, Tomas L. Sordo The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory . 2003,第47期

机译：β-内酰胺环断裂的理论研究：3-甲氧基-4-甲基-N-（亚乙基氨基）-2-氮杂环丁酮的臭氧分解
2. Ring Expansion of Alkylidenecarbenes Derived from Lactams, Lactones, and Thiolactones into Strained Heterocyclic Alkynes: A Theoretical Study [J] . Nguyen Nhat Thu Le, Just Josefine, Pankauski Jonathan M., Molecules . 2019,第3期

机译：源自内酰胺，内酰胺和硫灭菌剂的烷基砷烯酮的环形膨胀，进入应变杂环炔烃：理论研究
3. Synthesis of new β-carboline derivatives fused with β-lactam rings: An experimental and theoretical study [J] . Milen M., ábrányi-Balogh P., Mucsi Z., Current organic chemistry . 2013,第17期

机译：新型β-咔啉衍生物与β-内酰胺环稠合的合成：实验和理论研究
4. Cp~*Rh Complex-Catalyzed Synthesis of Five-,Six-,and Seven-Membered Ring Lactams from Amino Alcohols [C] . Ken-ichi Fuiila, Yoshinori Takahashi, Maki Owaki, Symposium on Organometallic Chemistry . 2004

机译：CP〜* rh复合催化合成氨基醇的五，六个和七元环内酰胺的合成
5. Structural studies of the beta-lactam ring-forming enzymes beta-lactam synthetase and carbapenam synthetase. [D] . Miller, Matthew Thomas. 2003

机译：β-内酰胺成环酶β-内酰胺合成酶和碳青霉烯合成酶的结构研究。
6. Ring Expansion of Alkylidenecarbenes Derived from Lactams Lactones and Thiolactones into Strained Heterocyclic Alkynes: A Theoretical Study [O] . Nguyen Nhat Thu Le, Josefine Just, Jonathan M. Pankauski, 2019

机译：内酰胺内酯和硫内酯衍生的亚烷基卡宾环扩链成杂环杂环炔烃的理论研究
7. Large ring 1,3-bridged 2-azetidinones: experimental and theoretical studies [O] . Urbach, Allan, Dive, Georges, Tinant, Bernard, 2009

机译：大环1,3-桥联的2-氮杂环丁酮：实验和理论研究

Theoretical Study of the Fragmentation of the β-Lactam Ring: Ozonolysis of 3-Methoxy-4-methyl-N-(ethylideneamino)-2-azetidinone

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