N,S-dibenzoyl-L-cysteine methyl ester | 236413-32-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,S-dibenzoyl-L-cysteine methyl ester
• 英文别名: methyl N,S-dibenzoylcysteinate；N,S-Dibenzoyl-L-cystein-methylester；methyl (2R)-2-benzamido-3-benzoylsulfanylpropanoate
• CAS: 236413-32-4
• 化学式: C₁₈H₁₇NO₄S
• 分子量: 343.403
• InChiKey: XMCXNZLFBGCHCT-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,S-dibenzoyl-L-cysteine methyl ester 在 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.08h， 生成 N-benzoyl-L-cysteine methyl ester
  参考文献：
  名称：

  The synthesis and structure of the derivatives of 2-deoxy-2-hydroxyimino-d-lyxo-hexopyranosyl-l-cysteine and -thiophenol

  摘要：

  3,4,6-Tri-O-acetyl-2-deoxy-2-hydroxyimino-beta and -alpha-D-lyxo-hexopyranosides of thiophenol (3, 4) and the methyl ester of N-benzoyl-L-cysteine have been synthesised by condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-alpha-D- galactopyranosyl chloride with thiophenol and the L-cysteine derivative, respectively. The conformation of the sugar residue and configuration of the anomeric centre as well as of the hydroxyimino group were established on the basis of the H-1 NMR (DQF-COSY, ROESY, TOCSY) spectrometric techniques and polarimetric data. Additionally, the structure of S-[3,4,6-tri-O-acetyl-2-deoxy-2-(Z)-hydroxyimino-beta-D-lyxo-hexopyranosyl]-thiophenol (3) was supported by X-ray diffraction data. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00035-5
• 作为产物：
  描述：

  L-半胱氨酸甲酯盐酸盐 、 苯甲酰氯 在 吡啶 作用下， 生成 N,S-dibenzoyl-L-cysteine methyl ester
  参考文献：
  名称：

  关于半胱氨酸和半胱氨酸肽。二、肽合成中的 S-酰基半胱氨酸

  摘要：

  分子模型显示，配体的三个供体组显示的平面排列中的应变非常低（如果有的话）。由于亚胺和芳环之间的共振倾向于将与亚胺氮相邻的键保持在同一平面上，因此 B 和 C 中所示配体的平面排列优于其他可能的结构。可以通过比较图 1 中的红外光谱获得所提出的螯合物结构的其他证据。在 2500-2600 cm 附近是否存在宽带。-l 表示 Cu(I1) 螯合物没有分子间氢键，而 Fe(II1) 和 Ni(I1) 螯合物的这种键合量增加。这些带的强度与无、一、和两个能够形成分子间氢键的吡啶鎓质子，分别如结构 A、B 和 C 所示。根据红外证据，对于 Fe(II1) 和 Ni(I1)，不能排除水与金属配位且 3-吡啶醇基团参与分子间氢键的替代结构。另一方面，根据已知的金属离子与有机配体中各种类型的供体基团之间的亲和力，这种替代结构被认为是不可能的。

  DOI：

  10.1021/ja00892a027

文献信息

• The use of phosphonium anhydrides for the synthesis of 2-oxazolines, 2-thiazolines and 2-dihydrooxazine under mild conditions
  作者：Maria J. Petersson、Ian D. Jenkins、Wendy A. Loughlin

  DOI：10.1039/b818310d

  日期：——

  β-Hydroxy amides6 and 7 were treated with triphenylphosphonium anhydride trifluoromethane sulfonate (3), or the cyclic analogue 4, to generate 2-oxazolines 5 and 8 under mild conditions. The reaction was optimised by examining the number of equivalents of reagents 3 or 4, or diisopropylethyl amine required to best effect cyclisation. The effects of altering the reaction temperature, reaction time,

  β-羟基酰胺6和7用三苯基anhydride酸酐三氟甲烷磺酸盐（3）或环状类似物4在温和条件下产生2-恶唑啉5和8。通过检查试剂3或4或二异丙基乙胺的当量数来优化反应，以达到最佳环化效果。还研究了改变反应温度，反应时间，浓度，溶剂和添加速率的影响。然而，发现使用三苯甲基来封闭起始酰胺的羟基或硫醇基团上的反应，以及随后在不存在碱的情况下进行原位去三苯甲基化反应，可以大大提高收率。试剂4 在提纯产品方面具有显着优势，可用于脱水一系列三苯甲基衍生物，以高产率（85-99％）生成四恶唑啉，噻唑啉和二氢-1,3-恶嗪，以及四氢呋喃。 -1,3-奥氮平（31％）。
• <b>On Cysteine and Cystine Peptides. I. New S-Protecting Groups for Cysteine</b>
  作者：Leonidas. Zervas、Iphigenia. Photaki

  DOI：10.1021/ja00879a019

  日期：1962.10
• Controllable Hydrogen Sulfide Donors and Their Activity against Myocardial Ischemia-Reperfusion Injury
  作者：Yu Zhao、Shashi Bhushan、Chuntao Yang、Hiroyuki Otsuka、Jason D. Stein、Armando Pacheco、Bo Peng、Nelmi O. Devarie-Baez、Hector C. Aguilar、David J. Lefer、Ming Xian

  DOI：10.1021/cb400090d

  日期：2013.6.21

  Hydrogen sulfide (H2S), known as an important cellular signaling molecule, plays critical roles in many physiological and/or pathological processes. Modulation of H2S levels could have tremendous therapeutic value. However, the study on H2S has been hindered due to the lack of controllable H2S releasing agents that could mimic the slow and moderate H2S release in vivo. In this work we report the design, synthesis, and biological evaluation of a new class of controllable H2S donors. Twenty-five donors were prepared and tested. Their structures were based on a perthiol template, which was suggested to be involved in H2S biosynthesis. H2S release mechanism from these donors was studied and proved to be thiol-dependent. We also developed a series of cell based assays to access their H2S-related activities. H9c2 cardiac rnyocytes were used M these experiments. We tested lead donors cytotoxicity and confirmed their H2S production in cells. Finally we demonstrated that selected donors showed potent protective effects in an in vivo murine model of myocardial ischemia-reperfuSion injury, through a H2S-related mechanism.
• Liberek; Frankowski; Smiatacz, Polish Journal of Chemistry, 1999, vol. 73, # 7, p. 1153 - 1161
  作者：Liberek、Frankowski、Smiatacz

  DOI：——

  日期：——
• Liberek; Smiatacz, Polish Journal of Chemistry, 2000, vol. 74, # 7, p. 989 - 996
  作者：Liberek、Smiatacz

  DOI：——

  日期：——