乙基2-(1-羟基乙基)-1,3-噻唑-4-羧酸酯 | 161891-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 乙基2-(1-羟基乙基)-1,3-噻唑-4-羧酸酯
• 英文名称: (+/-)-4-ethoxycarbonyl-2-(1-hydroxyethyl)thiazole
• 英文别名: ethyl 2-(1-hydroxyethyl)-4-thiazolecarboxylate；Ethyl 2-(1-hydroxyethyl)thiazole-4-carboxylate；ethyl 2-(1-hydroxyethyl)-1,3-thiazole-4-carboxylate
• CAS: 161891-80-1
• 化学式: C₈H₁₁NO₃S
• 分子量: 201.246
• InChiKey: YGMYQJINQIYLLW-UHFFFAOYSA-N

物化性质

• 沸点：
  297.1±20.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙基2-(1-羟基乙基)-1,3-噻唑-4-羧酸酯 在 戴斯-马丁氧化剂 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 2-乙酰基噻唑-4-羧酸
  参考文献：
  名称：

  Easy Access to 2-Alkyl and 2-Arylthiazolines Using a Modified Heteropolyacid Catalysis: Application to the Synthesis of Bacillamide A

  摘要：

  A straightforward access to 2-alkyl and 2-arylthiazolines by condensation of beta-aminothiols on nitriles, catalyzed by phosphotungstic acid (2%) under microwave irradiation, is described. This method has been directly applied to a short and efficient synthesis of bacillamide A (16).

  DOI：

  10.1080/00397911.2011.552834
• 作为产物：
  描述：

  3-(二乙氧基甲基)异噻唑 在 盐酸 作用下， 以 四氢呋喃 、 水 、 丙酮 、 甲苯 为溶剂， 反应 13.0h， 生成 乙基2-(1-羟基乙基)-1,3-噻唑-4-羧酸酯
  参考文献：
  名称：

  Easy Access to 2-Alkyl and 2-Arylthiazolines Using a Modified Heteropolyacid Catalysis: Application to the Synthesis of Bacillamide A

  摘要：

  A straightforward access to 2-alkyl and 2-arylthiazolines by condensation of beta-aminothiols on nitriles, catalyzed by phosphotungstic acid (2%) under microwave irradiation, is described. This method has been directly applied to a short and efficient synthesis of bacillamide A (16).

  DOI：

  10.1080/00397911.2011.552834

文献信息

• A Convenient Synthesis of Methyl 2-[2-(1-Amino)ethenyl-bithiazolyl] thiazoline-4-carboxylate, an Important Skeleton of Cyclothiazomycin
  作者：Chung-gi Shin、Akio Ito、Kazuo Okumura、Yutaka Nakamura

  DOI：10.1246/cl.1995.45

  日期：1995.1

  The convenient syntheses of a few methyl 2-(1-amino)alkenyl thiazoline-4-carboxylates and methyl 2-[2-(1-amino)ethenyl-bithiazolyl] thiazoline-4-carboxylate have been accomplished. The latter is an important partial skeleton of macrobicyclic peptide antibiotic cyclothiazomycin.

  一些2-(1-氨基)烯基噻唑啉-4-羧酸甲酯和2-[2-(1-氨基)乙烯基-联噻唑基]噻唑啉-4-羧酸甲酯的简便合成已经完成。后者是大双环肽类抗生素环噻霉素的重要部分骨架。
• Synthesis of Ozonolysis Products of Myxothiazol.
  作者：Hiroyuki AKITA、Masako NOZAWA、Shinji NAGUMO

  DOI：10.1248/cpb.42.1208

  日期：——

  By applying the Hantzsch thiazole procedure, the synthesis of bithiazole derivatives (2 and (±)-3) corresponding to degradation products of myxothiazol was achieved. Optically active (S)-3 (87-88% ee) and its analog (S)-16(91% ee) were obtained through enantioselective hydrolysis of the corresponding acetates ((±)-18, (±)-20 and (±)-21) using lipase in water-saturated organic solvent.

  通过应用 Hantzsch 噻唑程序，合成了与 myxothiazol 降解产物相对应的双噻唑衍生物（2 和 (±)-3）。利用脂肪酶在水饱和有机溶剂中对相应的醋酸盐（(±)-18、(±)-20 和 (±)-21）进行对映选择性水解，得到了具有光学活性的 (S)-3 (87-88% ee) 及其类似物 (S)-16 (91% ee)。
• ANTIIFLAMMATORY AND ANTITUMOR 2-OXOTHIAZOLES ABD 2-OXOTHIOPHENES COMPOUNDS
  申请人：AVEXXIN AS

  公开号：US20150376161A1

  公开（公告）日：2015-12-31

  A compound of formula (I) wherein X is O, C═O or S; Y is N or CH; R 2 and R 4 are each independently H, —(CH 2 ) p COOH, —(CH 2 ) p CON(R 5 ) 2 or —(CH 2 ) p COOC 1-6 alkyl; or R 2 and R 4 together form a 6-membered phenyl ring fused to the five membered ring; each R 1 is independently selected from H, halo (e.g. fluoro or chloro), C 6-10 aryl, C 7-12 arylalkyl, C 2-12 alkenyl; OC 1-12 alkyl, OC 2-12 alkenyl or a C 1-12 alkyl group; each R 5 is H or C 1-6 alkyl; each p is 0 to 3; n is 1 to 4; or a salt, ester, solvate, N-oxide, or prodrug thereof, e.g. a salt thereof

  化合物的式子(I)，其中X是O，C═O或S;Y是N或CH;R2和R4各自独立地为H，—(CH2)pCOOH，—(CH2)pCON(R5)2或—(CH2)pCOOC1-6烷基;或者R2和R4共同形成一个6成员苯环融合到五成员环上;每个R1独立地选自H，卤素（例如氟或氯），C6-10芳基，C7-12芳基烷基，C2-12烯丙基;OC1-12烷基，OC2-12烯丙基或C1-12烷基;每个R5是H或C1-6烷基;每个p为0到3;n为1到4;或其盐，酯，溶剂化物，N-氧化物或前药，例如其盐。
• 2-oxothiazole compounds and method of using same for chronic inflammatory disorders
  申请人：Avexxin AS

  公开号：US10370344B2

  公开（公告）日：2019-08-06

  The invention provides compounds of formula (I) wherein X is O or S; R1 is H, OH, SH, nitro, NH2, NHC1-6alkyl, N(C1-6alkyl)2, halo, haloC1-6alkyl, CN, C1-6-alkyl, OC1-6alkyl, C1-6alkylCOOH, C1-6alkylCOOC1-6alkyl, C2-6-alkenyl, C3-10cycloalkyl, C6-10aryl, C1-6alkylC6-10aryl, heterocyclyl, heteroaryl, CONH2, CONHC1-6alkyl, CON(C1-6alkyl)2, OCOC1-6alkyl, or is an acidic group, such as a group comprising a carboxyl, phosphate, phosphinate, sulfate, sulfonate, or tetrazolyl group; R2 is as defined for R1 or R1 and R2 taken together can form a 6-membered aromatic ring optionally substituted by up to 4 groups R5; R3 is H, halo (preferably fluoro), or CHal3 (preferably CF3); each R5 is defined as for R1; V1 is a covalent bond, —O—, or a C1-20alkyl group, or C2-20-mono or multiply unsaturated alkenyl group; said alkyl or alkenyl groups being optionally interrupted by one or more heteroatoms selected from O, NH, N(C1-6 alkyl), S, SO, or SO2; M1 is absent or is a C5-10 cyclic group or a C5-15 aromatic group; and R4 is H, halo, OH, CN, nitro, NH2, NHC1-6alkyl, N(C1-6alkylh, haloC1-6alkyl, a C1-20alkyl group, or C2-20-mono or multiply unsaturated alkenyl group, said C1-20alkyl or C2-20oalkenyl groups being optionally interrupted by one or more heteroatoms selected from O, NH, N(C1-6 alkyl), S, SO, or SO2; with the proviso that the group V1M1R4 as a whole provides at least 4 backbone atoms from the C(R3) group; or a salt, ester, solvate, N-oxide, or prodrug thereof; for use in the treatment of a chronic inflammatory condition.

  本发明提供了式 (I) 的化合物 其中 X 是 O 或 S； R1是H、OH、SH、硝基、NH2、NHC1-6烷基、N(C1-6烷基)2、卤素、卤代C1-6烷基、CN、C1-6烷基、OC1-6烷基、C1-6烷基COOH、C1-6烷基COOC1-6烷基、C2-6烯基、C3-10环烷基、C6-10芳基、C1-6烷基C6-10芳基、杂环烷基、杂芳基、CONH2、CONHC1-6烷基、CON(C1-6烷基)2、OCOC1-6烷基或酸性基团，如包含羧基、磷酸基、膦酸 基、硫酸基、磺酸基或四唑基的基团； R2 如 R1 所定义，或 R1 和 R2 可共同形成一个最多被 4 个基团 R5 任选取代的 6 元芳香环； R3 是 H、卤代（最好是氟代）或 CHal3（最好是 CF3）； 每个 R5 的定义与 R1 相同； V1 是共价键、-O-、或 C1-20 烷基、或 C2-20 单或多元不饱和烯基；所述烷基或烯基可选择被一个或多个选自 O、NH、N（C1-6 烷基）、S、SO 或 SO2 的杂原子打断； M1 不存在或为 C5-10 环状基团或 C5-15 芳香基团；以及 R4 是 H、卤素、OH、CN、硝基、NH2、NHC1-6烷基、N(C1-6烷基h、卤代 C1-6烷基、C1-20烷基或 C2-20 单或多不饱和烯基，所述 C1-20 烷基或 C2-20 烯基任选被一个或多个选自 O、NH、N(C1-6烷基)、S、SO 或 SO2 的杂原子打断； 但整个基团 V1M1R4 至少有 4 个来自 C（R3）基团的骨架原子； 或其盐、酯、溶液剂、N-氧化物或原药；用于治疗慢性炎症。
• Takayama, Hiroyuki; Kato, Keisuke; Kimura, Masayuki, Heterocycles, 2007, vol. 71, # 1, p. 75 - 85
  作者：Takayama, Hiroyuki、Kato, Keisuke、Kimura, Masayuki、Akita, Hiroyuki

  DOI：——

  日期：——