benzyl tetrahydro-2H-pyran-2-carboxylate | 84355-45-3

• 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: benzyl tetrahydro-2H-pyran-2-carboxylate
• 英文别名: Benzyl oxane-2-carboxylate
• CAS: 84355-45-3
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: WUMMYIJNLDSKPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  benzyl 2-diazo-6-hydroxyhexanoate 在 (R_a,S,S)-7,7'-bis(4-phenyl-4,5-dihydro-1,3-oxazolin-2-yl)-1,1'-spirobiindane 、 四(3,5-二(三氟甲基)苯基)硼酸钠 、 copper(l) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以91%的产率得到benzyl tetrahydro-2H-pyran-2-carboxylate
  参考文献：
  名称：

  Enantioselective Copper-Catalyzed Intramolecular O−H Insertion: An Efficient Approach to Chiral 2-Carboxy Cyclic Ethers

  摘要：

  A copper-catalyzed asymmetric intramolecular O-H insertion of omega-hydroxy-alpha-diazoesters has been accomplished by using chiral spiro bisoxazoline ligands. This highly enantioselective intramolecular O-H insertion reaction provides an efficient approach to a variety of synthetically important chiral 2-carboxy cyclic ethers with different ring sizes as well as substitution patterns.

  DOI：

  10.1021/ja1078464

文献信息

• [EN] 4-(2-FLUORO-4-METHOXY-5-3-(((1-METHYLCYCLOBUTYL)METHYL)CARBAMOYL)BICYCLO[2.2.1]HEPTAN-2-YL)CARBAMOYL)PHENOXY)-1-METHYLCYCLOHEXANE-1-CARBOXYLIC ACID DERIVATIVES AND SIMILAR COMPOUNDS AS RXFP1 MODULATORS FOR THE TREATMENT OF HEART FAILURE<br/>[FR] DÉRIVÉS D'ACIDE 4-(2-FLUORO-4-MÉTHOXY-5-3-(((1-MÉTHYLCYCLOBUTYLE)MÉTHYL)CARBAMOYL)BICYCLO[2.2.1]HEPTAN-2-YL) CARBAMOYL)PHÉNOXY)-1-MÉTHYLCYCLOHEXANE-1-CARBOXYLIQUE ET COMPOSÉS SIMILAIRES COMME MODULATEURS DE RXFP1 POUR LE TRAITEMENT DE L'INSUFFISANCE CARDIAQUE
  申请人：ASTRAZENECA AB

  公开号：WO2022122773A1

  公开（公告）日：2022-06-16

  The present invention relates to 4-(2-Fluoro-4-methoxy-5-3-(((l- methylcyclobutyl)methyl)carbamoyl)bicyclo[2.2.1]heptan-2-yl) carbamoyl)phenoxy)-l-methylcyclohexane-l-carboxylic acid derivatives and similar compounds of formula (I) as RXFP1 modulators for the treatment of heart failure, heart failure with preserved ejection fraction, heart failure with mid-range ejection fraction, heart failure with reduced ejection fraction, chronic kidney disease and acute kidney injury. The present invention also relates to crystalline forms of such compounds. An exemplary compound is e.g. (A).

  本发明涉及4-(2-氟-4-甲氧基-5-3-(((1-甲基环丁基)甲基)氨基)双环[2.2.1]庚烷-2-基)氨基苯氧基)-1-甲基环己烷-1-羧酸衍生物及类似化合物，其为RXFP1调节剂，用于治疗心力衰竭、保留射血分数的心力衰竭、中等射血分数的心力衰竭、降低射血分数的心力衰竭、慢性肾脏病和急性肾损伤。本发明还涉及这种化合物的晶体形式。一个示例化合物是例如(A)。
• Highly efficient synthesis of z-macrocycles using stereoretentive, ruthenium-based metathesis catalysts
  申请人：CALIFORNIA INSTITUTE OF TECHNOLOGY

  公开号：US11053209B2

  公开（公告）日：2021-07-06

  A highly efficient, Z-selective ring-closing metathesis system for the formation of macrocycles using a stereoretentive, ruthenium-based catalyst supported by a dithiolate ligand is reported. This catalyst is demonstrated to be remarkably active as observed in initiation experiments showing complete catalyst initiation at −20° C. within 10 min. Using easily accessible diene starting materials bearing a Z-olefin moiety, macrocyclization reactions generated products with significantly higher Z-selectivity in appreciably shorter reaction times, in higher yield, and with much lower catalyst loadings than in previously reported systems. Macrocyclic lactones ranging in size from twelve-membered to seventeen-membered rings are synthesized in moderate to high yields (68-79% yield) with excellent Z-selectivity (95%-99% Z).

  报告中介绍了一种高效的 Z 选择性闭环偏析系统，该系统使用了一种由二硫酸盐配体支持的立体定向钌基催化剂，用于形成大环。在引发实验中观察到，这种催化剂具有显著的活性，在 -20°C 温度下 10 分钟内就能完全引发。使用含有 Z-烯烃分子的易得二烯起始材料，大环化反应生成了 Z 选择性更高的产物，与之前报道的体系相比，反应时间明显更短、产率更高、催化剂负载量更低。合成的大环内酯大小从十二元环到十七元环不等，收率从中等到较高（68-79%），Z 选择性极佳（95%-99% Z）。
• A HIGHLY EFFICIENT SYNTHESIS OF Z-MACROCYLCES USING STEREORETENTIVE, RUTHENIUM-BASED METATHESIS CATALYSTS
  申请人：CALIFORNIA INSTITUTE OF TECHNOLOGY

  公开号：US20200102285A1

  公开（公告）日：2020-04-02

  A highly efficient, Z-selective ring-closing metathesis system for the formation of macrocycles using a stereoretentive, ruthenium-based catalyst supported by a dithiolate ligand is reported. This catalyst is demonstrated to be remarkably active as observed in initiation experiments showing complete catalyst initiation at −20° C. within 10 min. Using easily accessible diene starting materials bearing a Z-olefin moiety, macrocyclization reactions generated products with significantly higher Z-selectivity in appreciably shorter reaction times, in higher yield, and with much lower catalyst loadings than in previously reported systems. Macrocyclic lactones ranging in size from twelve-membered to seventeen-membered rings are synthesized in moderate to high yields (68-79% yield) with excellent Z-selectivity (95%-99% Z).