N-tosyl-L-prolyl chloride

• 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-tosyl-L-prolyl chloride
• 英文别名: N-tosyl-(S)-prolyl chloride；(2S)-1-(4-methylphenyl)sulfonylpyrrolidine-2-carbonyl chloride
• 化学式: C₁₂H₁₄ClNO₃S
• 分子量: 287.767
• InChiKey: LXXUQMYYLZNIFI-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-tosyl-L-prolyl chloride 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 1-(甲苯-4-磺酰基)-吡咯烷-2-羧酸
  参考文献：
  名称：

  Preparation of both enantiomers of 1-allyl-1,2,3,4-tetrahydro-β-carboline using allyltin reagents and a chiral auxiliary derived from l-proline

  摘要：

  beta -Carboline, which had an acyl group derived from L-proline at the 9-position, reacted with allyltributyltin and 2,2,2-trichloroethyl chloroformate, to afford an 1-allyl-1,2-dihydro-beta -carboline derivative in a diastereo selective manner. The chiral acyl group at N-9 was readily eliminated by aqueous alkali to give a corresponding carboxylic acid. The formed 1-allyl-1,2-dihydro-beta -carboline was transformed via two reduction steps to 1-alkyl-1,2,3,4-tetrahydro-beta -carboline in high ee. When the allylation was carried out using tetraallyltin instead of allyltributyltin, the stereoselectivity was reversed, and the antipode of the allyl adduct was obtained in high yield and ee in the presence of tin(IV) tetraiodide. Thus, it was found that both enantiomers of 1-allyl-beta -carboline were obtained in good enantioselectivities by the use of the same chiral auxiliary. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00684-6
• 作为产物：
  描述：

  1-(甲苯-4-磺酰基)-吡咯烷-2-羧酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 N-tosyl-L-prolyl chloride
  参考文献：
  名称：

  7- [3-（1-氨基烷基）吡咯烷基]-和7- [3-1-氨基环烷基]吡咯烷基]-喹诺酮抗菌剂的合成及构效关系。

  摘要：

  已经制备了一系列的7- [3-（1-氨基烷基和1-氨基环烷基）-1-吡咯烷基]喹诺酮并评估了它们的生物学特性。其中，1-（S）-氨基烷基衍生物对革兰氏阳性和革兰氏阴性生物显示出有效的抗菌活性。与氨基甲基同类物相比，它们具有中等的亲脂性和较高的水溶性。例如，3-（1-氨基乙基）-1-吡咯烷基化合物（83）的药代动力学特性优于其氨基甲基对应物（6）。

  DOI：

  10.1248/cpb.42.1442

文献信息

• Synthesis of enantiomers of 3-methyl- and 3-phenyl-3,4-dihydro-2H-[1,4]benzothiazines and their 1,1-dioxides via an acylative kinetic resolution protocol
  作者：Dmitry A. Gruzdev、Evgeny N. Chulakov、Liliya Sh. Sadretdinova、Mikhail I. Kodess、Galina L. Levit、Victor P. Krasnov

  DOI：10.1016/j.tetasy.2015.01.010

  日期：2015.2

  (ee >97%). This method proved to be less suitable for the preparation of the (S)-enantiomer of 3,4-dihydro-3-phenyl-2H-[1,4]benzothiazine (ee up to 93%) and its sulfone (ee 82%) which were both obtained in low yields. The loss of enantioselectivity for (S)-3,4-dihydro-3-phenyl-2H-[1,4]benzothiazine and its sulfone occurred during hydrolysis of the corresponding diastereoisomerically pure amides.

  已经发现，（的酰氯小号） -萘普生，Ñ -phthaloyl-（小号） -亮氨酸，和Ñ甲苯磺酰基（小号） -脯氨酸是外消旋的3-甲基的acylative动力学拆分高效手性拆分试剂和3-苯基-3,4-二氢-3-甲基-2 ħ - [1,4]苯并噻嗪。基于该实验结果，包括acylative动力学拆分制备性协议，随后通过单个（主）非对映体酰胺和酰胺键的随后水解分离，提出了。使用与各种手性拆分剂该方法中，（小号） -和（- [R）3,4-二氢-3-甲基-2 -对映体ħ-得到[1,4]苯并噻嗪（EE> 99％）。酰胺的非对映体相应的氧化，随后导致了（脱酰小号） -和（- [R ）-对映体的3,4-二氢-3-甲基-2 ħ - [1,4]苯并噻嗪1,1-二氧化钛（ee值> 97％）。这种方法被证明是不适合的（制备小号）3,4-二氢-3-苯基-2 -对映体ħ - [1,4]苯并噻嗪（EE高达93％）和它的砜（EE
• Newly designed acylsilanes as versatile tools in organic synthesis
  作者：Bianca F Bonini、Mauro Comes-Franchini、Mariafrancesca Fochi、Germana Mazzanti、Alfredo Ricci

  DOI：10.1016/s0022-328x(98)00694-9

  日期：1998.9

  Structural variations in acylsilane molecules allow a number of new selective synthetic processes to be performed which lead to sulfur-containing heterocycles, highly functionalized and unsaturated polycarbonyl derivatives, polyenes, and β- and γ-aminoalcohols. The synthesis of these compounds, most of them not easily accessible through conventional routes, takes advantage of the site-selective reactions

  酰基硅烷分子的结构变化允许执行许多新的选择性合成工艺，这些工艺会导致含硫杂环，高度官能化和不饱和的多羰基衍生物，多烯以及β-和γ-氨基醇。这些化合物的合成（大多数都不易通过常规途径获得）利用C-Si键处发生的位点选择反应，相对于相应醛而言，酰基硅烷的稳定性提高以及SiR 3引入的非对面选择性团体。在本文中，我们报告了导致几种功能化酰基硅烷的合成及其合成应用的不同合成策略。还将介绍使用新的选择性多金属试剂进行亲核甲硅烷基化的方法。
• Conformationally Constrained Dipeptide Surrogates with Aromatic Side-Chains:  Synthesis of 4-Aryl Indolizidin-9-one Amino Acids by Conjugate Addition to a Common α,ω-Diaminoazelate Enone Intermediate
  作者：Jérôme Cluzeau、William D. Lubell

  DOI：10.1021/jo0355855

  日期：2004.3.1

  Four methyl 9-oxo-8-(N-(Boc)-amino)-4-phenyl-1-azabicyclo[4.3.0]nonane carboxylates (11, 4-Ph-I9aa-OMe) were synthesized from (2S,8S,5E)-di-tert-butyl-4-oxo-5-ene-2,8-bis[N-(PhF)amino]azelate [(5E)-7, PhF = 9-(9-phenylfluorenyl)] via a seven-step process featuring a conjugate addition/reductive amination/lactam cyclization sequence. Various nucleophiles were used in the conjugate addition reactions

  四个甲基-9-氧代-8-（ñ - （BOC） -氨基）-4-苯基-1-氮杂双环[4.3.0]壬烷羧酸（11，4-PH-I 9 AA-OME）从（2合成S，8 S，5 E）-二叔丁基-4-氧代-5-烯-2,8-双[ N-（PhF）氨基]壬二酸酯[（5 E）-7，PhF = 9-（ 9-苯基芴基）]通过共轭加成/还原胺化/内酰胺环化序列为特征的七步过程。烯酮（5 E）-7的共轭加成反应中使用了各种亲核试剂作为制备具有不同取代基的α，ω-二氨基壬二酸酯的一般途径，尽管非对映选择性低，但芳基格氏试剂（9/1至15/1 drs）除外。通过色谱法和非对映选择性沉淀分离6-苯基壬二酸酯（6 S）-8d和（6 R）-8d，并独立地转化成4-Ph-1 I 9 aa-OMe。由（6 S）-8d选择性地以51％的产率制备（2 S，4 R，6 R，8 S）-4-Ph-I 9 aa-OMe 11。（6还原胺化- [R
• Synthesis, enantiomeric separation and docking studies of spiropiperidine analogues as ligands of the nociceptin/orphanin FQ receptor
  作者：Umberto M. Battisti、Sandra Corrado、Claudia Sorbi、Andrea Cornia、Annalisa Tait、Davide Malfacini、Maria Camilla Cerlesi、Girolamo Calò、Livio Brasili

  DOI：10.1039/c4md00082j

  日期：——

  A series of triazospirodecanone derivatives were synthesized as potential NOP ligands. 8-(Chroman-4-yl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (4) and its 5-fluoro analogue (18) proved to be active as agonists with EC50 values in the submicromolar range. Single enantiomers of compound 4 were separated and tested as NOP agonists; the eutomer R-(+)-4 showed a pEC50 of 7.34. Finally docking studies were performed on the NOP receptor to identify the most significant stereospecific interactions.

  一系列三氮杂螺癸烷-4-酮衍生物被合成作为潜在的NOP配体。8-(色满-4-基)-1-苯基-1,3,8-三氮杂螺[4.5]癸烷-4-酮（4）及其5-氟类似物（18）被证明是具有亚微摩尔级EC50值的激动剂。化合物4的单一旋光异构体被分离并测试为NOP激动剂；优旋体R-(+)-4显示出7.34的pEC50值。最后，对NOP受体进行了对接研究，以识别最重要的立体特异性相互作用。
• Structure–Activity Relationship Studies with Tetrahydroquinoline Analogs as EPAC Inhibitors
  作者：Yogesh A. Sonawane、Yingmin Zhu、Jered C. Garrison、Edward L. Ezell、Muhammad Zahid、Xiaodong Cheng、Amarnath Natarajan

  DOI：10.1021/acsmedchemlett.7b00358

  日期：2017.11.9

  metastasis. Several laboratories use a tetrahydroquinoline analog, CE3F4, to dissect the role of EPAC1 in various disease states. Here, we report SAR studies with tetrahydroquinoline analogs that explore various functional groups. The most potent EPAC inhibitor 12a exists as a mixture of inseparable E (major) and Z (minor) rotamers. The rotation about the N-formyl group indeed impacts the activity against

  EPAC蛋白是潜在治疗心脏肥大和癌症转移的治疗靶标。一些实验室使用四氢喹啉类似物CE3F4来剖析EPAC1在各种疾病状态中的作用。在这里，我们报道了使用四氢喹啉类似物探索各种功能基团的SAR研究。最有效的EPAC抑制剂12a以不可分离的E（主要）和Z（次要）旋转异构体的混合物形式存在。围绕N-甲酰基的旋转确实影响了针对EPAC的活性。