甲苯磺酸-(2-羟基-3-丁烯)酯 | 138332-13-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 甲苯磺酸-(2-羟基-3-丁烯)酯
• 英文名称: 2-hydroxybut-3-enyl-4-methylbenzenesulfonate
• 英文别名: 1-tosyloxy-3-buten-2-ol；2-hydroxy-3-butene-1-(p-toluenesulfonate)；(±)-2-hydroxybut-3-enyl tosylate；2-hydroxybut-3-en-1-yl 4-methylbenzenesulfonate；toluene-4-sulfonic acid 2-hydroxy-but-3-enyl ester；2-hydroxy-3-butenyl-4-methyl-1-benzenesulfonate；2-hydroxy-3-buten-1-yl p-tosylate；1-tosyloxy-2-hydroxy-3-butene；(+/-)-2-Hydroxy-3-buten-1-yl tosylate；2-hydroxybut-3-enyl 4-methylbenzenesulfonate
• CAS: 138332-13-5
• 化学式: C₁₁H₁₄O₄S
• mdl: MFCD30076512
• 分子量: 242.296
• InChiKey: YQSCDBZHHLIPOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲苯磺酸-(2-羟基-3-丁烯)酯 在 吡啶 、 phosphate buffer 、 Pseudomonas Amano PS lipase 作用下， 反应 6.75h， 生成 (R)-2-羟基-3-丁烯-1-对甲苯磺酸
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiomerically pure alkene 1,2-diols and glycosides thereof

  摘要：

  The kinetic resolution of racemic 2-O-acylated 3-butene-1,2-diol and 1-O-acylated 3-butene-1,2-diol derivatives by enzymatic saponification and enzymatic esterification, respectively, is investigated with several lipases and esterases. The resulting partially blocked enantiomers are glycosylated with glycosyl halides and trichloroacetimidates, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00051-2
• 作为产物：
  描述：

  丁烯二醇 、 对甲苯磺酰氯 在 吡啶 作用下， 以 氯仿 为溶剂， 以94.3%的产率得到甲苯磺酸-(2-羟基-3-丁烯)酯
  参考文献：
  名称：

  通过无尖锐的不对称环氧化途径合成对映体纯的3-丁烯-1,2-二醇衍生物。

  摘要：

  描述了丁烯二醇单甲苯磺酸酯（1,2,3），环氧丁二醇单甲苯磺酸酯（3,4）和环氧丁烷（5,6）的短对映体合成。

  DOI：

  10.1016/0040-4039(93)85026-s

文献信息

• Macrocyclic Modulators of the Ghrelin Receptor
  申请人：Ocera Therapeutics, Inc.

  公开号：US20180110824A1

  公开（公告）日：2018-04-26

  The present invention provides novel conformationally-defined macrocyclic compounds that have been demonstrated to be selective modulators of the ghrelin receptor (growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, gastrointestinal disorders, cardiovascular disorders, obesity and obesity-associated disorders, central nervous system disorders, genetic disorders, hyperproliferative disorders and inflammatory disorders.

  本发明提供了一种新颖的构象定义明确的大环化合物，已经证明是生长激素分泌素受体（GHS-R1a及其亚型、异构体和变体）的选择性调节剂。本文还描述了合成这些新型化合物的方法。这些化合物可用作生长激素分泌素受体的激动剂，用于治疗和预防一系列医疗状况，包括但不限于代谢和/或内分泌紊乱、胃肠道紊乱、心血管疾病、肥胖和与肥胖相关的疾病、中枢神经系统疾病、遗传疾病、过度增殖性疾病和炎症性疾病。
• Enantioselective Synthesis of Cyclic, Quaternary Oxonitriles
  作者：Yakup Güneş、M. Fatih Polat、Ertan Sahin、Fraser F. Fleming、Ramazan Altundas

  DOI：10.1021/jo1011202

  日期：2010.11.5

  Quaternary oxonitriles are stereoselectively generated from the union of five-, six-, and seven-membered 2-chloroalkenecarbonitriles with chiral alcohols via a Claisen rearrangement. The strategy rests on a new conjugate addition−elimination of allylic alkoxides to 2-chlorocycloalkenecarbonitriles to afford substituted 2-alkoxyalkenenitriles. Subsequent thermolysis unmasks a cyclic oxonitrile while

  五元，六元和七元的2-氯烯烃腈与手性醇通过克莱森重排的结合立体选择性地生成季腈。该策略基于新的共轭加成-将烯丙基醇盐消除到2-氯环烯腈中，得到取代的2-烷氧基烯腈。随后的热解反应会掩盖环状氧腈，同时选择性地形成对映体比率通常大于9：1的新季铵中心。整体烷基化策略解决了对映选择性地生成受阻的四级中心同时安装酮，腈和烯烃官能团的挑战。
• MACROCYCLIC GHRELIN RECEPTOR MODULATORS AND METHODS OF USING THE SAME
  申请人：Hoveyda Hamid

  公开号：US20080194672A1

  公开（公告）日：2008-08-14

  The present invention provides novel conformationally-defined macrocyclic compounds that can function as selective modulators of the ghrelin receptor (growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, gastrointestinal disorders, cardiovascular disorders, obesity and obesity-associated disorders, central nervous system disorders, bone disorders, genetic disorders, hyperproliferative disorders and inflammatory disorders.

  本发明提供了一种新颖的构象定义明确的大环化合物，可以作为生长激素分泌素受体（GHS-R1a及其亚型、异构体和变体）的选择性调节剂。本文还描述了合成这些新型化合物的方法。这些化合物可用作生长激素分泌素受体的激动剂，用于治疗和预防一系列医疗状况，包括但不限于代谢和/或内分泌紊乱、胃肠道紊乱、心血管疾病、肥胖和与肥胖相关的疾病、中枢神经系统疾病、骨骼疾病、遗传疾病、过度增生性疾病和炎症性疾病。
• Enzyme-mediated enantioselective hydrolysis of 1,2-diol monotosylate derivatives bearing an unsaturated substituent
  作者：K. Matsumoto、K. Oohana、M. Hashimoto、K. Usuda、T. Shimoda、H. Ohshima、Y. Suzuki、T. Togawa

  DOI：10.1016/j.tet.2018.05.087

  日期：2018.7

  We have succeeded in the easy preparation of optically active 1,2-diol monotosylates bearing an unsaturated substituent via enzymatic hydrolysis. Lipase PS quickly catalyzes the hydrolyses of 2-acetoxybut-3-enyl tosylate, which has a double bond, and 2-acetoxybut-3-ynyl tosylate, which has a triple bond, with excellent enantioselectivity to afford the corresponding optically active compounds. The reaction

  我们已经成功地通过酶水解容易地制备了带有不饱和取代基的光学活性的1,2-二醇单甲苯磺酸酯。脂肪酶PS快速催化具有双键的2-乙酰氧基丁-3-烯基甲苯磺酸酯和具有三键的2-乙酰氧基丁-3-炔基甲苯磺酸酯的水解，具有出色的对映选择性，可提供相应的旋光化合物。该反应也适用于在末端具有双键的较长链的乙酸酯。为了证明该方法的适用性，已从外消旋的2-乙酰氧基戊-4-烯基甲苯磺酸酯中分几步合成了对映体纯的（R）-马苏阿内酯，一种天然椰子香精。此外，该酶可以识别烯烃的立体化学，而（Z）-烯基结构比（E）-异构体更适合于对映选择性水解。
• CDPK1 INHIBITORS, COMPOSITIONS, AND METHODS RELATED THERETO
  申请人：Vyera Pharmaceuticals, LLC

  公开号：US20210347780A1

  公开（公告）日：2021-11-11

  The invention relates to inhibitors of calcium-dependent protein kinase 1 (CDPK1) and pharmaceutical preparations thereof. The invention further relates to methods of treatment of parasitic infections, such as T. gondii, P. falciparum, C. hominis , or C. parvum infections, using the novel inhibitors of the invention.

  该发明涉及钙依赖性蛋白激酶1（CDPK1）的抑制剂及其药物制剂。该发明进一步涉及使用该发明的新型抑制剂治疗寄生虫感染的方法，例如弓形虫、疟原虫、人类小肠球虫或小肠球小弓形虫感染。