3-溴双环[1.1.1]戊烷-1-羧酸 | 156329-70-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 3-溴双环[1.1.1]戊烷-1-羧酸
• 英文名称: 3-bromobicyclo<1.1.1>pentane-1-carboxylic acid
• 英文别名: 3-bromobicyclo[1.1.1]pentane-1-carboxylic Acid
• CAS: 156329-70-3
• 化学式: C₆H₇BrO₂
• mdl: MFCD20621126
• 分子量: 191.024
• InChiKey: VWLOBPGTTZYAPT-UHFFFAOYSA-N

物化性质

• 沸点：
  275.8±40.0 °C(Predicted)
• 密度：
  2.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-溴双环[1.1.1]戊烷-1-羧酸 在 三氯三氟乙烷 、 N,N'-二环己基碳二亚胺 作用下， 生成 (2-Sulfanylidenepyridin-1-yl) 3-tert-butylbicyclo[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-thioxo-1,2-dihydropyridin-1-yl 3-(methoxycarbonyl)bicyclo<1.1.1>pentane-1-carboxylate 在 氟烷 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 3-溴双环[1.1.1]戊烷-1-羧酸
  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

文献信息

• Design and Structure–Activity Relationships of Isothiocyanates as Potent and Selective <i>N</i>-Acylethanolamine-Hydrolyzing Acid Amidase Inhibitors
  作者：Michael S. Malamas、Spiro Pavlopoulos、Shakiru O. Alapafuja、Shrouq I. Farah、Alexander Zvonok、Khadijah A. Mohammad、Jay West、Nicholas Thomas Perry、Dimitrios N. Pelekoudas、Girija Rajarshi、Christina Shields、Honrao Chandrashekhar、Jodi Wood、Alexandros Makriyannis

  DOI：10.1021/acs.jmedchem.1c00076

  日期：2021.5.13

  of inflammatory and pain processes. The synthesis and structure-activity relationship studies encompassing the isothiocyanate pharmacophore have produced potent low nanomolar inhibitors for hNAAA, while exhibiting high selectivity (>100-fold) against other serine hydrolases and cysteine peptidases. We have followed a target-based structure–activity relationship approach, supported by computational methods

  N-酰基乙醇胺是信号脂质分子，参与与炎症和疼痛相关的病理生理状况。N-乙酰乙醇胺酸酰胺酶（NAAA）有利地水解脂质棕榈酰乙醇酰胺，其在调节炎症和疼痛过程中起关键作用。涉及异硫氰酸酯药效团的合成和构效关系研究已经产生了针对hNAAA的有效的低纳摩尔抑制剂，同时对其他丝氨酸水解酶和半胱氨酸肽酶表现出高选择性（> 100倍）。我们遵循了基于目标的结构-活性关系方法，并得到了计算方法和hNAAA的已知共晶的支持。我们已经鉴定出具有良好血浆稳定性的全身活性抑制剂（t1/2 > 2 h）和微粒体稳定性（t 1 /2〜15–30 min）作为研究NAAA在炎症，疼痛和药物成瘾中的作用的药理学工具。
• Adcock, William; Binmore, Gavin T.; Krstic, Alexander R., Journal of the American Chemical Society, 1995, vol. 117, # 10, p. 2758 - 2766
  作者：Adcock, William、Binmore, Gavin T.、Krstic, Alexander R.、Walton, John C.、Wilkie, John

  DOI：——

  日期：——
• 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：——
• Synthesis of Some Bridgehead-Bridgehead-Disubstituted Bicyclo[1.1.1]pentanes
  作者：Ernest W. Della、Dennis K. Taylor

  DOI：10.1021/jo00090a015

  日期：1994.6

  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.