Tropinone

Tropinone 속성

Tropinone MSDS

Tropinone

Tropinone C화학적 특성, 용도, 생산

개요

Tropinone (8-methyl-8-azabicyclo[3.2.1]octane-3-one)(7) is the simplest plant tropane and is the first intermediate in the biosynthesis of tropane alkaloids.  Studies have called 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoic acid as an intermediate metabolite in tropinone biosynthesis[1]. It is an intermediate of atropine sulfate and is used in the synthesis of atropine. Atropine is an anticholinergic drug. It acts as an M-blocker and is indicated for the relief of visceral colic.

화학적 성질

Tropinone is a white to light yellow crystal powder, It is an alkaloid and a precursor to a number of additional plant alkaloids. Tropinone is the first intermediate in the biosynthesis of the pharmacologically important tropane alkaloids that possesses the 8-azabicyclo[3.2.1]octane core bicyclic structure that defines this alkaloid class. Chemical synthesis of tropinone was achieved in 1901 but the mechanism of tropinone biosynthesis has remained elusive.

용도

Tropinone is an oxidative product of Tropane, used to synthesize Morphine and Tropane alkaloids.

제조 방법

The first synthesis of tropinone was by Richard Willstätter in 1901. It started from the seemingly related cycloheptanone, but required many steps and had an overall yield of only 0.75%.Willstätter had previously synthesized cocaine from tropinone, in what was the first synthesis and elucidation of the structure of cocaine.
The 1917 synthesis by Robinson is considered a legend in total synthesis due to its simplicity and biomimetic approach. Tropinone is a bicyclic molecule, but the reactants used in its preparation are fairly simple: succinaldehyde, methyl amine and acetone dicarboxylic acid (or even acetone). The synthesis is a good example of a biomimetic reaction or biogenetic-type synthesis because biosynthesis makes use of the same building blocks. It also demonstrates a tandem reaction in a one-pot synthesis. Furthermore the yield of the synthesis was 17% and with subsequent improvements exceeded 90%.

참고 문헌

1. Arthur J. Birch. Investigating a Scientific Legend: The Tropinone Synthesis of Sir Robert Robinson, F.R.S. Notes and Records of the Royal Society of London, 1993, 47, 277-296. DOI:10.1098/rsnr.1993.0034
2. Andrew J. Humphrey and David O'Hagan. Tropane alkaloid biosynthesis. A century old problem unresolved. Natural Products Reports 2001, 18, 494-502. DOI:10.1039/b001713m
3. Tropinone synthesis via an atypical polyketide synthase and P450-mediated cyclization DOI:10.1038/s41467-018-07671-3
4. R. Robinson (1917). "A synthesis of tropinone". Journal of the Chemical Society, Transaction 111: 762 - 768. doi:10.1039/CT9171100762

Tropinone 준비 용품 및 원자재

원자재

준비 용품

Tropinone 공급 업체

공급자	전화	이메일	국가	제품 수	이점
Hebei Yanxi Chemical Co., Ltd.	+8617531190177	peter@yan-xi.com	China	5993	58
Zhejiang ZETian Fine Chemicals Co. LTD	18957127338	stella@zetchem.com	China	2141	58
Anhui Yiao New Material Technology Co., Ltd	+86-199-55145978 +8619955145978	sales8@anhuiyiao.com	China	253	58
Beijing Mediking Biopharm Co., Ltd	+undefined15901403431	sales01@mediking.cn	China	150	58
Dorne Chemical Technology co. LTD	+86-13583358881 +86-18560316533	Ethan@dornechem.com	China	294	58
Hong Kong Excellence Biotechnology Co., Ltd.	+86-86-18838029171 +8618126314766	ada@sh-teruiop.com	China	893	58
Xiamen Wonderful Bio Technology Co., Ltd.	+8613043004613	Sara@xmwonderfulbio.com	China	305	58
Shaanxi Haibo Biotechnology Co., Ltd	+undefined18602966907	qinhe02@xaltbio.com	China	1000	58
Shandong Hanjiang Chemical Co., Ltd	+86-0533-2066820 +8618369939125	hanson@sdhanjiang.com	China	1527	58
Shaanxi Franta Biotechnology Co., Ltd	+86-13082019107 +86-13082019107	admin@flanderff.com	China	229	58

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