2-(naphthalen-2-yl)ethyl 4-methylbenzenesulfonate | 7175-35-1

• 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: 2-(naphthalen-2-yl)ethyl 4-methylbenzenesulfonate
• 英文别名: 2-Naphthaleneethanol, 2-(4-methylbenzenesulfonate)；2-naphthalen-2-ylethyl 4-methylbenzenesulfonate
• CAS: 7175-35-1
• 化学式: C₁₉H₁₈O₃S
• 分子量: 326.416
• InChiKey: XRFAOLIKBJIPII-UHFFFAOYSA-N

物化性质

• 沸点：
  513.8±29.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(naphthalen-2-yl)ethyl 4-methylbenzenesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-(2-azidoethyl)naphthalene
  参考文献：
  名称：

  Melanocortin receptor ligands

  摘要：

  公开了MC-4和/或MC-3受体配体，该配体具有按照式（I）的结构：其中R2、R4、R4'、R5、R6、R6'、R7、R8、R8'、R9、R9'、R10、Ar、Z1、Z2、Z3、X、B、D、p、q、r和s如说明书和索赔中所述，以及其光学异构体、二对映异构体或对映体；药用盐、水合物和生物水解酯、酰胺或亚酰胺。还公开了包括式（I）配体的药物组合物，以及治疗由MC-4/MC-3受体介导的疾病的方法，如说明书的详细描述部分所述。

  公开号：

  US20060128613A1
• 作为产物：
  描述：

  2-萘乙酸 在 lithium aluminium tetrahydride 作用下， 生成 2-(naphthalen-2-yl)ethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Effect of solvent on .beta.-arylalkyl solvolysis

  摘要：

  DOI：

  10.1021/ja00469a040

文献信息

• Nucleophilic Trifluoromethylthiolation of Alkyl Chlorides, Bromides and Tosylates
  作者：Chunfa Xu、Qingyun Chen、Qilong Shen

  DOI：10.1002/cjoc.201500905

  日期：2016.5

  A direct nucleophilic trifluoromethylthiolation of alkyl chlorides, bromides and tosylates with AgSCF3 was described. It was found that the presence of nBu4NI or a combination of nBu4NI/nBu4NBr significantly enhanced the reaction rates. The reaction conditions were mild, thus allowing the tolerance of a variety of functional groups.

  描述了用AgSCF 3烷基氯，溴化物和甲苯磺酸酯的直接亲核三氟甲基硫醇化。发现存在n Bu 4 NI或n Bu 4 NI / n Bu 4 NBr的组合显着提高了反应速率。反应条件温和，因此允许各种官能团的耐受性。
• Stereoselective synthesis of enantiopure analogues of (−)-cephalotaxine
  作者：Farouk Berhal、Joëlle Pérard-Viret、Jacques Royer

  DOI：10.1016/j.tetasy.2010.01.004

  日期：2010.3

  The asymmetric total synthesis of three analogues of (−)-cephalotaxine with structural modification of the aromatic ring was achieved in 16 steps and acceptable overall yields. The procedure used was quite similar to that reported by our group for the total synthesis of (−)-cephalotaxine in 2004. The enantiopure spiranic compound 4 is a common intermediate on which various aromatic groups can be introduced

  通过16个步骤和可接受的总收率实现了（-）-头孢他辛的三种类似物的芳烃环结构修饰的不对称全合成。使用的程序与我们小组在2004年报告的（-）-头孢他辛的全合成过程非常相似。对映纯螺烷化合物4是常见的中间体，可以在其上引入各种芳族基团。在这些合成过程中观察到了意外的和有趣的不同化学行为。
• Discovery of SMP-304, a novel benzylpiperidine derivative with serotonin transporter inhibitory activity and 5-HT1A weak partial agonistic activity showing the antidepressant-like effect
  作者：Hidefumi Yoshinaga、Shuji Masumoto、Koji Koyama、Naoya Kinomura、Yuji Matsumoto、Taro Kato、Satoko Baba、Kenji Matsumoto、Tomoko Horisawa、Hitomi Oki、Kazuki Yabuuchi、Toru Kodo

  DOI：10.1016/j.bmc.2016.10.034

  日期：2017.1

  We report the discovery of a novel benzylpiperidine derivative with serotonin transporter (SERT) inhibitory activity and 5-HT1A receptor weak partial agonistic activity showing the antidepressant-like effect. The 3-methoxyphenyl group and the phenethyl group of compound 1, which has weak SERT binding activity, but potent 5-HT1A binding activity, were optimized, leading to compound 35 with potent and

  我们报告发现具有5-羟色胺转运蛋白（SERT）抑制活性和5-HT1A受体弱部分激动活性的新型苄基哌啶衍生物，显示出抗抑郁样作用。优化了化合物1的3-甲氧基苯基和苯乙基，它们具有弱的SERT结合活性，但具有有效的5-HT1A结合活性，从而导致化合物35具有有效且平衡的双重SERT和5-HT1A结合活性，而且有效的CYP2D6抑制活性。用较大的烷氧基（例如乙氧基，异丙氧基或甲氧基-乙氧基）代替化合物35左侧部分中的甲氧基可改善CYP2D6的抑制作用，从而使SMP-304成为候选化合物。具有5-羟色胺摄取抑制活性和5-HT1A弱局部激动活性的SMP-304，可作为5-HT1A拮抗剂起作用，
• 2,6-diazaspiro[3.4]octan-7-one derivatives as potent sigma-1 receptor antagonists that enhanced the antinociceptive effect of morphine and rescued morphine tolerance
  作者：Kequan Fu、Wen Xu、Ruicong Yang、Huimin Zhao、Huanyu Xu、Yaqin Wei、Hongli Liu、Yinli Qiu、Danqi Chen、Dong Guo、Bing Xiong

  DOI：10.1016/j.ejmech.2023.115178

  日期：2023.3

  antagonists harboring the 2,6-diazaspiro[3.4]octan-7-one scaffold. Through a detailed structure-activity relationship study, we identified compound 32 as a potent σ1R antagonist, which significantly enhanced the antinociceptive effect of morphine and rescued morphine-induced analgesic tolerance. Our results support σ1R antagonism as a promising strategy to develop novel analgesics and highlight the therapeutic

  阿片类药物是治疗疼痛的有效镇痛药。但大剂量重复使用常导致镇痛耐受，限制了其临床应用。据报道，Sigma-1 受体 (σ1R) 拮抗剂可协同增强mu阿片受体 (MOR) 激动剂的镇痛效果，且不会放大不良反应。因此，σ1R 被认为是一个有前途的疼痛管理药物靶点。基于最近阐明的σ1R与4-IBP的共晶结构，我们设计并开发了一系列含有2,6-diazaspiro[3.4]octan-7-one支架的σ1R拮抗剂。通过详细的构效关系研究，我们确定化合物32是一种有效的 σ1R 拮抗剂，可显着增强吗啡的镇痛作用并挽救吗啡引起的镇痛耐受。我们的结果支持 σ1R 拮抗作为开发新型镇痛药的有前途的策略，并强调化合物32预防吗啡耐受的治疗潜力。
• Piperidyl - urea, - thiourea and - guanidine derivatives, and intermediates therefor, processes for preparing them and pharmaceutical compositions containing the derivatives
  申请人：JOHN WYETH & BROTHER LIMITED

  公开号：EP0035374A2

  公开（公告）日：1981-09-09

  The invention concerns psychotropic agents useful as antidepressants having the formula and acid addition and quaternary ammonium salts thereof, wherein the dotted line represents an optional bond, Ar represents a ring system of formula in which Q is O,S,-CR7=CR8- and -N=N-; R4, R5 and R6, and R7 and R8 when present, each represent hydrogen or defined substituents and additionally either R4 and R5 when adjacent or R6 and R8 when adjacent, together with the carbon atoms to which they are attached also represent a fused five or six membered carbocyclic or heterocyclic ring optionally carrying one or more defined substituents; R is an optionally substituted aryl or heteroaryl radical or a cycloalkyl radical containing 5 to 7 carbon atoms; R1, R2, R3 and R9 are each hydrogen or a lower alkyl group; n is 0 or 1; X is =0, =S or =NH; Y is -O- or a direct bond and Z is -CO- or -CH2- with the proviso that when Ar is unsubstituted phenyl and R9 is hydrogen then Y is -0-. Processes for preparing the compounds and pharmaceutical compositions containing them are also disclosed. Analogues having a pyridinium ring or ZR representing hydrogen are also disclosed as intermediates.

  本发明涉及可用作抗抑郁剂的精神药物，其化学式为 及其酸加成盐和季铵盐，其中虚线代表任选键，Ar 代表式 其中 Q 是 O、S、-CR7=CR8- 和 -N=N-；R4、R5 和 R6 以及 R7 和 R8（当存在时）各自代表氢或定义的取代基，此外，R4 和 R5（当相邻时）或 R6 和 R8（当相邻时）与它们所连接的碳原子一起还代表可选带一个或多个定义取代基的融合的五或六成员碳环或杂环；R是任选取代的芳基或杂芳基或含有5至7个碳原子的环烷基；R1、R2、R3和R9各自是氢或低级烷基；n是0或1；X是＝0、＝S或＝NH；Y是-O-或直接键，Z是-CO-或-CH2-，但当Ar是未取代的苯基且R9是氢时，则Y是-0-。 此外，还公开了制备这些化合物和含有这些化合物的药物组合物的工艺。还公开了具有吡啶鎓环或 ZR 代表氢的类似物作为中间体。