1,1-dioxo-tetrahydro-1λ⁶-thiophene-2-carboxylic acid ethyl ester | 18342-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: 1,1-dioxo-tetrahydro-1λ⁶-thiophene-2-carboxylic acid ethyl ester
• 英文别名: 2-Carbethoxy-tetrahydro-thiophen-1-dioxid；Ethyl 1,1-dioxothiolane-2-carboxylate
• CAS: 18342-43-3
• 化学式: C₇H₁₂O₄S
• 分子量: 192.236
• InChiKey: QWHXVLGXBYWSGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-dioxo-tetrahydro-1λ⁶-thiophene-2-carboxylic acid ethyl ester 在 三正丁胺 、 间氯过氧苯甲酸 作用下， 反应 4.0h， 生成 ethyl 10-<(tetrahydropyran-2'-yl)oxy>-(2E,4E)-decadienoate
  参考文献：
  名称：

  Saigo, Kazuhiko; Kudo, Kazuaki; Hashimoto, Yukihiko, Chemistry Letters, 1989, p. 1203 - 1206

  摘要：

  DOI：

文献信息

• Potent Inhibitors of LpxC for the Treatment of Gram-Negative Infections
  作者：Matthew F. Brown、Usa Reilly、Joseph A. Abramite、Joel T. Arcari、Robert Oliver、Rose A. Barham、Ye Che、Jinshan Michael Chen、Elizabeth M. Collantes、Seung Won Chung、Charlene Desbonnet、Jonathan Doty、Matthew Doroski、Juntyma J. Engtrakul、Thomas M. Harris、Michael Huband、John D. Knafels、Karen L. Leach、Shenping Liu、Anthony Marfat、Andrea Marra、Eric McElroy、Michael Melnick、Carol A. Menard、Justin I. Montgomery、Lisa Mullins、Mark. C. Noe、John O’Donnell、Joseph Penzien、Mark S. Plummer、Loren M. Price、Veerabahu Shanmugasundaram、Christy Thoma、Daniel P. Uccello、Joseph S. Warmus、Donn G. Wishka

  DOI：10.1021/jm2014748

  日期：2012.1.26

  In this paper, we present the synthesis and SAR as well as selectivity, pharmacokinetic, and infection model data for representative analogues of a novel series of potent antibacterial LpxC inhibitors represented by hydroxamic acid 1a.
• CARBOCYCLIC AND HETEROCYCLIC HIV PROTEASE INHIBITORS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0641306A1

  公开（公告）日：1995-03-08
• [EN] CARBOCYCLIC AND HETEROCYCLIC HIV PROTEASE INHIBITORS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：WO1992021647A1

  公开（公告）日：1992-12-10

  (EN) Compounds of formula (I) wherein R1 and R4 are OH, (CHR5)mCOR6, (CHR5)mCH(OH)R5 or R5; R2 and R3 are H, C1-8alkyl, Het, C3-10cycloalkyl, Het-C1-8alkyl, C2-8alkenyl, Het-C2-8alkenyl, C3-10cycloalkyl-C1-8alkyl or C3-10cycloalkyl-C2-8alkenyl; R5 is R2 or R2 mono- or di-substituted by G; R6 is H, OH, OR', R2, N(R')2, AA or NHC(=NR7)NHR''; R7 is H, CN, COR' or SO2R'; R' is H, C1-6alkyl, C3-10cycloalkyl or C1-8alkyl-C3-10cycloalkyl; R'' is R', COR', C(O)OR' or CON(R')2; G is OR', OC(O)R', OC(O)N(R')2, halogen, COR6, NR'-AA, NHCOR', SO2N(R')2, NHSO2N(R')2, NHC(=NR7)NHR'', CF3 or N(R')2; AA is one or two amino acids; Z is CH2, CHOH, CHN(R')2, CHNHCOOR, S, SO, SO2, SONH, O, CHCH2OH, CHCO2H, C=O, NR'', N(O)R' or C=NHOR'; Q is CHOH, S, SO or SO2; m is 0, 1 or 2; n is 0 or 1; and pharmaceutically acceptable salts thereof, inhibit the HIV-1 protease and are useful in the treatment of AIDS.(FR) Composés de formule (I) dans laquelle R1 et R4 représentent OH, (CHR5)mCOR6, (CHR5)mCH(OH)R5 ou R5; R2 et R3 représentent H, C1-8alkyle, Het, C3-10cycloalkyle, Het-C1-8alkyle, C2-8alkényle, Het-C2-8alkényle, C3-10cycloalkyle-C1-8alkyle ou C3-10cycloalkyle-C2-8alkényle; R5 représente R2 ou R2 mono ou bisubstitué par G; R6 représente H, OH, OR', R2, N(R')2, AA ou NHC(=NR7)NHR''; R7 représente H, CN, COR' ou SO2R'; R' représente H, C1-6alkyle, C3-10cycloalkyle ou C1-8alkyleC3-10cycloalkyle; R'' représente R', COR', C(O)OR' ou CON(R')2; G représente OR', OC(O)R', OC(O)N(R')2, halogène, COR6, NR'-AA, NHCOR', SO2N(R')2, NHSO2N(R')2, NHC(=NR7)NHR'', CF3 ou N(R')2; AA représente un ou deux amino acides; Z représente CH2, CHOH, CHN(R')2, CHNHCOOR, S, SO, SO2, SONH, O, CHCH2OH, CHCO2H, C=O, NR'', N(O)R' ou C=NHOR'; Q représente CHOH, S, SO ou SO2; m vaut 0, 1 ou 2; n vaut 0 ou 1; et leurs sels pharmaceutiquement acceptables, inhibent la protéase du HIV-1 et sont utiles dans le traitement du SIDA.