2-thioxo-1,2-dihydropyridin-1-yl 3-(methoxycarbonyl)bicyclo<1.1.1>pentane-1-carboxylate | 156329-69-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-thioxo-1,2-dihydropyridin-1-yl 3-(methoxycarbonyl)bicyclo<1.1.1>pentane-1-carboxylate
• 英文别名: 1-O-methyl 3-O-(2-sulfanylidenepyridin-1-yl) bicyclo[1.1.1]pentane-1,3-dicarboxylate
• CAS: 156329-69-0
• 化学式: C₁₃H₁₃NO₄S
• 分子量: 279.317
• InChiKey: ILOSYQOATCRLDE-UHFFFAOYSA-N

物化性质

• 沸点：
  370.3±52.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  87.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-thioxo-1,2-dihydropyridin-1-yl 3-(methoxycarbonyl)bicyclo<1.1.1>pentane-1-carboxylate 在 氟烷 作用下， 反应 1.0h， 以95%的产率得到methyl 3-bromobicyclo[1.1.1]pentane-1-carboxylate
  参考文献：
  名称：

  Synthesis of Some Bridgehead-Bridgehead-Disubstituted Bicyclo[1.1.1]pentanes

  摘要：

  The synthesis of a wide variety of 1,3-disubstituted bicyclo[1.1.1]pentanes is described, with particular emphasis on the generation of a series of S-X-substituted bicyclo[1.1.1]pentyl bromides required for solvolytic studies. Functional group manipulation at the bridgehead was readily accomplished in the majority of cases by radical processes in some instances, transformations were effected via carbanionic-type intermediates.

  DOI：

  10.1021/jo00090a015
• 作为产物：
  描述：

  2-mercaptopyridine-1-oxide sodium salt 、 3-(甲氧基羰基)二环[1.1.1]戊烷-1-羧酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 2-thioxo-1,2-dihydropyridin-1-yl 3-(methoxycarbonyl)bicyclo<1.1.1>pentane-1-carboxylate
  参考文献：
  名称：

  3-羧基/ 3-氨基双环[1.1.1]戊烷衍生的磺酰胺和磺酰氟–用于有机合成和药物发现的高级双功能试剂

  摘要：

  描述了由相应的羧酸合成双官能双环[1.1.1]戊烷衍生的磺酰氟，磺酰胺和亚磺酸盐，包括经典磺酰胺抗生素的等规类似物。

  DOI：

  10.1002/ejoc.202000303

文献信息

• [EN] AZOBENZENE COMPOUND AND APPLICATION THEREOF<br/>[FR] COMPOSÉ AZOBENZÈNE ET SON APPLICATION<br/>[ZH] 氮杂联苯类化合物及其应用
  申请人：[en]CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.;[zh]正大天晴药业集团股份有限公司

  公开号：WO2023078463A1

  公开（公告）日：2023-05-11

  一种氮杂联苯类化合物及其应用，具体公开了式(A)所示化合物及其药学上可接受的盐。
• Bridgehead Carbocations: A Solvolytic Study of 1-Bromobicyclo[1.1.1]pentane and Its Bridgehead-Substituted Derivatives
  作者：Ernest W. Della、Cyril A. Grob、Dennis K. Taylor

  DOI：10.1021/ja00093a014

  日期：1994.7

  The rate constants (k) for solvolysis of a range of 3-X-substituted bicyclo[1.1.1]pentyl bromides in 80% aqueous ethanol have been measured and a linear relationship found to exist between log k and the inductive/field constant sigma(I). These observations, together with the results of isotope and solvent effect studies described below, have been interpreted as evidence for the formation of 1-bicyclo[1.1.1]pentyl cations in the ionization step in preference to mechanisms in which either ring-opening is concerted with ionization to give 3-methylenecyclobutyl cations or ionization is accompanied by ring-contraction to give bicyclo[1.1.0]butyl-1-carbinyl cations. The latter mechanisms would have been expected to show the effects of strong pi-donor substituent participation, a phenomenon which was not observed. A comparison of the rates of solvolysis of the parent bromide and its 3-deuterated analog is characterized by a large deuterium-isotope effect (k(H)/k(D) = 1.30) which, combined with the observation that 1-bromobicyclo[1.1.1]pentane solvolyses with enhanced rates in solvents which are strong hydrogen bonding accepters, lends support to the view that the 1-bicyclo[1.1.1]pentyl cation derives substantial stabilization from sigma-hyperconjugative interactions.
• Della Ernest W., Taylor Dennis K., J. Org. Chem, 59 (1994) N 11, S 2986-2996
  作者：Della Ernest W., Taylor Dennis K.

  DOI：——

  日期：——