methyl thioallophanate | 51863-38-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl thioallophanate
• 英文别名: methyl carbamothioylcarbamate；N-Methoxycarbonylthioharnstoff；3-thio-allophanic acid methyl ester；3-Thio-allophansaeure-methylester；β-Thioallophansaeure-methylester；N-Carbomethoxy-thioharnstoff；Carbamic acid, N-(aminohioxomethyl)-, methyl ester；methyl N-carbamothioylcarbamate
• CAS: 51863-38-8
• 化学式: C₃H₆N₂O₂S
• mdl: MFCD19203986
• 分子量: 134.159
• InChiKey: MKFSHVVOAIQUGS-UHFFFAOYSA-N

物化性质

• 密度：
  1.172 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  96.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl thioallophanate 生成 N-氨基甲酰氨基甲酸甲酯
  参考文献：
  名称：

  Studies on Organic Sulfur Compounds. XIII. The Oxidation Reaction of Alkoxycarbonylthioureas with Bromine

  摘要：

  N-烷氧基羰基硫脲（A）与溴在氯仿中反应，生成硫、烷氧基羰基脲（B）、3, 5-双（烷氧基羰基亚氨基）-1, 2, 4-二硫杂戊烷（C）、3, 5-双（烷氧基羰基氨基）-1, 2, 4-噻二唑（D）、2-烷氧基羰基-5-烷氧基羰基氨基-3-亚氨基-1, 2, 4-噻二唑啉（E）和3-氨基-5-烷氧基羰基氨基-1, 2, 4-噻二唑（F）。本文详细描述了这些反应产物结构的确认。

  DOI：

  10.1248/cpb.21.2396
• 作为产物：
  描述：

  异硫氰酰甲酸甲酯 在 ammonium hydroxide 作用下， 以 乙酸乙酯 为溶剂， 反应 0.25h， 生成 methyl thioallophanate
  参考文献：
  名称：

  Ayyangar, N. R.; Lahoti, R. J.; Daniel, Thomas, Organic Preparations and Procedures International, 1991, vol. 23, # 5, p. 627 - 632

  摘要：

  DOI：

文献信息

• Thiourea participation in [3+2] cycloaddition with donor–acceptor cyclopropanes: a domino process to 2-amino-dihydrothiophenes
  作者：Ming-Sheng Xie、Guo-Feng Zhao、Tao Qin、Yong-Bo Suo、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1039/c8cc09595g

  日期：——

  The Yb(OTf)3-catalyzed [3+2] cycloaddition of donor–acceptor cyclopropanes with thiourea offers an efficient route to diverse 2-amino-4,5-dihydrothiophenes (up to 92% yield), in which optically active 2-amino-dihydrothiophenes can be produced from enantiomerically pure cyclopropanes. Thiourea, which is an odorless and cheap reagent, provides a CS double bond, serves as an amino source, and functions

  Yb（OTf）3催化的供体-受体环丙烷与硫脲的[3 + 2]环加成反应提供了一种有效的途径来制备各种2-氨基-4,5-二氢噻吩（产率高达92％），其中旋光性2-氨基-二氢噻吩可由对映体纯的环丙烷产生。硫脲是一种无味且廉价的试剂，具有C S双键，可作为氨基源，并在该反应中用作脱碳烷氧基化试剂。初步的机理研究表明，该反应经历了依次的[3 + 2]环加成/脱氨基/脱羧过程。
• Chiusoli, Gian Paolo; Costa, Mirco; Pergreffi, Paola, Gazzetta Chimica Italiana, 1985, vol. 115, # 12, p. 691 - 696
  作者：Chiusoli, Gian Paolo、Costa, Mirco、Pergreffi, Paola、Reverberi, Sara、Salerno, Giuseppe

  DOI：——

  日期：——
• Dixon; Kennedy, Journal of the Chemical Society, 1920, vol. 117, p. 76
  作者：Dixon、Kennedy

  DOI：——

  日期：——
• Discovery of a Potent and Selective Noncovalent Linear Inhibitor of the Hepatitis C Virus NS3 Protease (BI 201335)
  作者：Montse Llinàs-Brunet、Murray D. Bailey、Nathalie Goudreau、Punit K. Bhardwaj、Josée Bordeleau、Michael Bös、Yves Bousquet、Michael G. Cordingley、Jiamin Duan、Pat Forgione、Michel Garneau、Elise Ghiro、Vida Gorys、Sylvie Goulet、Ted Halmos、Stephen H. Kawai、Julie Naud、Marc-André Poupart、Peter W. White

  DOI：10.1021/jm100690x

  日期：2010.9.9

  C-Terminal carboxylic acid containing inhibitors of the NS3 protease are reported. A novel series of linear tripeptide inhibitors that are very potent and selective against the NS3 protease are described. A substantial contribution to the potency of these linear inhibitors arises from the introduction of a C8 substituent on the B-ring of the quinoline moiety found on the P2 of these inhibitors. The introduction of a CS methyl group results not only in a modest increase in the cell-based potency of these inhibitors but more importantly in a much better pharmacokinetic profile in rats as well. Exploration of C8-substitutions led to the identification of the bromo derivative as the best group at this position, resulting in a significant increase in the cell-based potency of this class of inhibitors. Structure activity studies on the C8-bromo derivatives ultimately led to the discovery of clinical candidate 29 (BI 201335), a very potent and selective inhibitor of genotypel NS3 protease with a promising PK profile in rats.
• Doran, Journal of the Chemical Society, 1901, vol. 79, p. 910
  作者：Doran

  DOI：——

  日期：——