Synthesis of (3aS,6aR)-1,3-Dibenzyl-tetrahydro-1H- thieno[3,4-d]-imidazole-2(3H)-one-4-ylidenepentanoic Acid and Characterization of Its Crystal

被引：0
|
作者：
YUAN Jian-Li a WANG Jing-Mei b CHEN Fen-Er a② a (Department of Chemistry
机构：
来源：
结构化学 | 2004年 / 06期
关键词：
Grignard reaction; synthesis; X-ray crystal structure;
D O I：
10.14102/j.cnki.0254-5861.2004.06.003
中图分类号：
O621 [有机化学一般性问题];
学科分类号：
摘要：
The intermediate of d-biotin, (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4- d]-imidazole-2(3H)-one-4-ylidenepentanoil acid was synthesized from (3aS,6aR)-1,3-dibenzylte- trahyro-4H-thieno[3,4-d]-imidazole-2,4(1H)-dione by using the Grignard reaction. The structure of 3 was characterized by IR, 1H NMR and MS, and the absolute configuration was further confirmed by X-ray crystal structure analysis. Compound 3 crystallizes in monoclinic, space group P21 with a = 11.030(2), b = 7.783(2), c = 12.797(2) , b = 93.44(1)o, Z = 2, Mr = 422.53 (C24H26N2O3S), V = 1096.3(6) 3, = 0.177 mm-1, Dc = 1.280 g/cm3, F(000) = 448 and T = 293(2) K. The final R = 0.0737 and Rw = 0.1974 for 1009 observed reflections with I >2s(I).
引用
收藏
页码：507 / 510 +496
页数：5
相关论文
共 50 条
  • [31] NEW ORGANIC NITRATES .2. SYNTHESIS OF 2H-PYRIDO[2,3-E]-1,3-OXAZINE-2,4(3H)-DIONES, 2H-PYRIDO[4,3-E]-1,3-OXAZINE-2,4(3H)-DIONES, 2H-PYRIDO[4,3-E]-1,3-OXAZIN-4(3H)-ONES, 2H-THIENO[2,3-E]-1,3-OXAZIN-4(3H)-ONES AND 2H-THIENO[3,4-E]-1,3-OXAZIN-2,4(3H)-DIONES
    BENEDINI, F
    BERTOLINI, G
    FERRARIO, F
    MOTTI, A
    SALA, A
    SOMENZI, F
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (01) : 103 - 107
  • [32] 1,3-Bis(naphthalen-2-ylmethyl)-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione
    Afrakssou, Zahra
    Rodi, Youssef Kandri
    Capet, Frederic
    Essassi, El Mokhtar
    Ng, Seik Weng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2138 - U1444
  • [33] STRUCTURE OF 2-SELENOXOPERHYDRO-2H-THIENO[3,4-D][1,3]DITHIOLE 5,5-DIOXIDE
    MOLINS, E
    VECIANA, J
    MIRAVITLLES, C
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1993, 49 : 1129 - 1130
  • [34] The crystal structure of 1,5-dibenzyl-1H-pyrazolo[3,4-d]pyrimidine-4(5H)-thione
    El Fal, Mohammed
    Ramli, Youssef
    Essassi, El Mokhtar
    Saadi, Mohamed
    El Ammari, Lahcen
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : O95 - U406
  • [35] Tetrahydro-6-methyl-1H,3H-thieno[3,4-b]-pyrrol-2-one, an analogue of biotin
    Mackay, MF
    Henderson, SA
    Savage, GP
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1995, 51 (pt 12) : 2673 - 2674
  • [36] STRUCTURE OF A GLYCOURIL DERIVATIVE - TETRAHYDRO-1,6-3,4-DI(METHANOXYMETHANO)-3A,6A-DIMETHYLIMIDAZO[4,5-D]IMIDAZOLE-2,5(1H,3H)-DIONE
    SCHOUTEN, A
    KANTERS, JA
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1990, 46 : 2484 - 2486
  • [37] (3aS,6aR)-1,3-双(4-甲氧苄基)-四氢-1H-噻吩并[3,4-d]咪唑-2,4-二酮的不对称合成
    李丹
    熊方均
    熊非
    陈芬儿
    中国医药工业杂志, 2014, 45 (10) : 919 - 923
  • [38] Spiro[carbazole-1(2H),2′-[1,3]dithiolan]-4(3H)-one
    Hokelek, T
    Gunduz, H
    Patir, S
    Uludag, N
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1998, 54 : 1297 - 1299
  • [39] Synthesis, structure, Hirshfeld surface, crystal voids, energy framework and DFT analysis of 1H-benzo[d]imidazole-2(3H)-thione
    Singh, M.
    Anthal, S.
    Kamal
    Deshmukh, M. B.
    Kant, Rajni
    INDIAN JOURNAL OF CHEMISTRY, 2022, 61 (05): : 528 - 536
  • [40] HIGHLY EFFECTIVE RESOLUTION OF 1,3-DIBENZYL-6-HYDROXY-3,3A,6,6A-TETRAHYDRO-1H-FURO[3,4-D]IMIDAZOLE-2,4-DIONE, AN INTERMEDIATE FOR BIOTIN, WITH OPTICALLY-ACTIVE AMINES AND REUTILIZATION OF THE UNWANTED EPIMER
    SENUMA, M
    FUJII, T
    SETO, M
    OKAMURA, K
    DATE, T
    KINUMAKI, A
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (04) : 882 - 887
12345