(R)-噻唑烷-4-甲酸甲酯 | 42258-90-2

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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
• 中文名称: (R)-噻唑烷-4-甲酸甲酯
• 英文名称: (R)-thiazolidine-4-carboxylic acid methyl ester
• 英文别名: Methyl (R)-thiazolidine-4-carboxylate；methyl (4R)-1,3-thiazolidine-4-carboxylate
• CAS: 42258-90-2
• 化学式: C₅H₉NO₂S
• mdl: MFCD09881016
• 分子量: 147.198
• InChiKey: NHBNAVLHRAPNKY-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (R)-噻唑烷-4-甲酸甲酯 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (4R)-thiazolidine-4-carboxamide
  参考文献：
  名称：

  Study of the structural requirements for Dopa potentiation and oxotremorine antagonism by L-prolyl-L-leucylglycinamide

  摘要：

  A number of analogs of the tripeptide L-prolyly-L-leucylglycinamide (1) were synthesized and evaluated in the Dopa potentiation and oxotremorine antagonism tests. The replacement of the glycinamide residue with either the glycine methylamide, glycine, aminoacetonitrile, amino-2-propanone, semicarbazide, or beta-alaninamide residues resulted in a loss of activity in both tests. A 1:1 mixture of L-prolyl-L-leucyl-(-)-thiazolidine-2-carboxamide (8) and L-prolyl-L-leucyl-(+)-thiazolidine-2-carboxamide (9) showed marked activity in the Dopa potentiation test but was unable to antagonize the tremors induced by oxotremorine. L-Prolyl-L-leucyl-L-prolinamide (11), on the other hand, was active in the oxotremorine antagonism test but inactive in the Dopa potentiation test. The replacement of the pyrrolidine ring of 1 with either a thiazolidine or cyclopentane ring system caused a loss of activity. The cyclopentanecarboxylic acid analogue 13, however, was found to have moderate activity in the serotonin potentiation test.

  DOI：

  10.1021/jm00200a004
• 作为产物：
  描述：

  L-硫代脯氨酸 在 盐酸 作用下， 生成 (R)-噻唑烷-4-甲酸甲酯
  参考文献：
  名称：

  The Action of Formaldehyde upon Cysteine

  摘要：

  DOI：

  10.1021/ja01280a050

文献信息

• d-Penicillamine and l-cysteine derived thiazolidine catalysts: an efficient approach to both enantiomers of secondary alcohols
  作者：M. Elisa Silva Serra、Dora Costa、Dina Murtinho、Nélia C.T. Tavares、Teresa M.V.D. Pinho e Melo

  DOI：10.1016/j.tet.2016.08.036

  日期：2016.9

  d-Penicillamine derived thiazolidine ligands were prepared in a two-step synthetic sequence and used in the enantioselective alkylation of a variety of aromatic aldehydes with diethylzinc at room temperature. Excellent ee, up to >99%, and nearly complete conversions were observed. Structurally analogous l-cysteine derived thiazolidine ligands were also synthesized and tested for comparative purposes

  d-青霉胺衍生的噻唑烷配体以两步合成顺序制备，并在室温下用于各种芳香醛与二乙基锌的对映选择性烷基化。优秀的ee，高达> 99％，并且观察到几乎完全的转换。还合成了结构相似的1-半胱氨酸衍生的噻唑烷配体，并进行了比较试验，结果显示出很好的选择性，尽管选择性略低，最高可达89％。两种噻唑烷的组合使用构成合成（S）和（R）手性仲醇的对映异构体，从而引出了无数有用的具有相反绝对构型的旋光产物。
• A one-pot three-component synthesis of dithiocarbamates starting from vinyl pyridines and vinyl pyrazine under solvent- and catalyst-free conditions
  作者：Azim Ziyaei Halimehjani、Jürgen Martens、Torben Schlüter

  DOI：10.1016/j.tet.2016.05.025

  日期：2016.7

  A novel and efficient one-pot three-component reaction for the synthesis of dithiocarbamates at room temperature under solvent- and catalyst-free conditions, starting from readily available amines, CS2 and vinyl pyridines and vinyl pyrazine is reported. Excellent yield, green reaction conditions, and complete regioselectivity toward anti-Markovnikov adducts are particular advantages of this work.

  报道了一种新颖且有效的一锅三组分反应，该反应在室温下在无溶剂和无催化剂的条件下从容易获得的胺，CS 2和乙烯基吡啶以及乙烯基吡嗪开始合成二硫代氨基甲酸酯。出色的收率，绿色反应条件和对反马尔科夫尼科夫加合物的完全区域选择性是这项工作的特别优势。
• X = Y - ZH systems as potential 1,3-dipoles. Part 40. Chiral azomethine ylides from homochiral cyclic α-amino esters. Unusual regiospecific deprotonation of iminium ions.
  作者：Ronald Grigg、Zoran Rankovic、Mark Thornton-Pett、Anoma Somasunderam

  DOI：10.1016/s0040-4020(01)96273-8

  日期：1993.9

  of iminium ions from cyclic secondary α-amino esters and bifunctional carbonyl compounds and their regiospecific or regioselective conversion to homochiral azomethine ylides. The endo-exo selectivity in the cycloadditions of these azomethine ylides is sensitive to the bifunctional carbonyl compound employed.

  甲1,3 -应变和电荷加速1,5-H位移在从环状仲α氨基酯和双官能的羰基化合物和它们的区域专一或区域选择性转化为纯手性甲亚胺叶立德立体有择形成亚胺离子的重要因素。这些偶氮甲亚胺基团的环加成中的内-外选择性对所用的双官能羰基化合物是敏感的。
• The steric effect and enantioselectivity of chiral 2,2-disubstituted thiaprolinol derivatives as ligands for borane reduction of aromatic ketones and for diethylzinc addition to aromatic aldehydes
  作者：Hsiang-Ling Huang、Ya-Chuan Lin、Shyh-Fong Chen、Chia-Lin J. Wang、Lee Tai Liu

  DOI：10.1016/0957-4166(96)00399-0

  日期：1996.11

  chiral amino alcohols 3a-e has been prepared from natural amino acid L-cysteine. These compounds have been used as chiral ligands for borane reduction of ketones and for diethylzinc addition to aldehydes. In the reduction of ketones, 3b-e have been used as the substitute of (R)-prolinol to provide (S)-alcohols in good yields and modest enantioselectivity (30–50% ee). In the diethylzinc addition to aldehydes

  从天然氨基酸L-半胱氨酸制备了一系列新的手性氨基醇3a-e。这些化合物已用作手性配体，用于酮的硼烷还原和除醛以外的二乙基锌。在还原酮中，3b-e已被用作（R）-脯氨醇的替代品，以高收率和适度的对映选择性（30–50％ee）提供（S）醇。除醛中的二乙基锌外，3b-e以优异的产率和中等至良好的对映选择性（60-80％ee）促进了（S）醇的形成。
• Potent and selective proline derived dipeptidyl peptidase IV inhibitors
  作者：Scott D. Edmondson、Anthony Mastracchio、Maria Beconi、Lawrence F. Colwell、Bahanu Habulihaz、Huaibing He、Sanjeev Kumar、Barbara Leiting、Kathryn A. Lyons、Ann Mao、Frank Marsilio、Reshma A. Patel、Joseph K. Wu、Lan Zhu、Nancy A. Thornberry、Ann E. Weber、Emma R. Parmee

  DOI：10.1016/j.bmcl.2004.07.056

  日期：2004.10

  In-house screening of the Merck sample collection identified proline derived homophenylalanine 3 as a DPP-IV inhibitor with modest potency (DPP-IV IC50=1.9 microM). Optimization of 3 led to compound 37, which is among the most potent and selective DPP-IV inhibitors discovered to date.

  对Merck样品的内部筛选表明，脯氨酸衍生的高苯丙氨酸3作为DPP-IV抑制剂具有中等效力（DPP-IV IC50 = 1.9 microM）。对3的优化导致化合物37，它是迄今为止发现的最有效和选择性最强的DPP-IV抑制剂之一。