toluene-4-sulfonic acid 2-(2-bromophenyl)ethyl ester | 171734-72-8

• 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: toluene-4-sulfonic acid 2-(2-bromophenyl)ethyl ester
• 英文别名: 2-(2'-bromophenyl)ethyl 4-methylbenzenesulfonate；2-bromophenethyl 4-methylbenzenesulfonate；2-bromophenethyl-4-methylbenzenesulfonate；2-(2-bromophenyl)ethyl tosylate；2-bromophenethyl tosylate；2-(2-bromophenyl)ethyl 4-toluenesulfonate；2-(2-Bromophenyl)ethyl 4-methylbenzenesulfonate
• CAS: 171734-72-8
• 化学式: C₁₅H₁₅BrO₃S
• 分子量: 355.252
• InChiKey: QJKZCWWFBYCGPK-UHFFFAOYSA-N

物化性质

• 熔点：
  38-39 °C
• 沸点：
  472.9±33.0 °C(Predicted)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  toluene-4-sulfonic acid 2-(2-bromophenyl)ethyl ester 在 四(三苯基膦)钯 、 palladium on activated charcoal 、 氢气 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~80.0 ℃ 、101.33 kPa 条件下， 反应 73.0h， 生成 吡喹酮
  参考文献：
  名称：

  钯催化的分子内Heck /加氢合成吡喹酮

  摘要：

  从3-甲氧基N-酰基吡嗪鎓盐开始，已经开发了合成抗血吸虫病药物吡喹酮（PZQ）的新方法。利用钯催化的分子内Heck反应形成脱氢-PZQ，然后以逐步或一锅法的氢化步骤，以4或5个步骤以克级合成PZQ，且总收率良好。事实证明，该方法非常适合于生成PZQ的吡嗪并[1,2-a]异吲哚和吡嗪并[1,2-a]苯并ze庚因类似物。

  DOI：

  10.1016/j.tet.2017.10.006
• 作为产物：
  描述：

  邻溴苯乙酸 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 toluene-4-sulfonic acid 2-(2-bromophenyl)ethyl ester
  参考文献：
  名称：

  Mapping the Melatonin Receptor. 6. Melatonin Agonists and Antagonists Derived from 6H-Isoindolo[2,1-a]indoles, 5,6-Dihydroindolo[2,1-a]isoquinolines, and 6,7-Dihydro-5H-benzo[c]azepino[2,1-a]indoles

  摘要：

  6H-Isoindolo[2,1-a]indoles (5, 7, 10, 13), 5,6-dihydroindolo[2,1-a]isoquinolines (20, 21), and 6,7-dihydro-5H-benzo[c]azepino[2,1-a]indoles (23, 25, 27, 30) have been prepared as melatonin analogues to investigate the nature of the binding site of the melatonin receptor. The affinity of analogues was determined in a radioligand binding assay using cloned human mt(1) and MT2 receptor subtypes expressed in NIH 3T3 cells. Agonist and antagonist potency was measured using the pigment aggregation response of a clonal line of Xenopus laevis melanophores. The 2-methoxyisoindolo[2,1-a]indoles (7a-d) showed much higher binding affinities than the parent isoindoles (5a-e), and whereas 7a-c were agonists in the functional assay, 7d and 5a-e were antagonists. The 2-ethoxyisoindolo[2,1-a]indoles (10a-d) showed reduced binding affinities compared to their methoxy analogues, while the 5-chloro derivative 13 showed a considerable reduction in binding affinity and potency compared to 7a. The 10-methoxy-5,6-dihydroindolo[2,1-a]isoquinolines (21a-c) had higher binding affinities than the corresponding parent indoloisoquinolines (20a-c) in the human receptor subtypes, and the parent compounds were antagonists whereas the 10-methoxy derivatives were agonists in the functional assay. The N-cyclobutanecarbonyl derivatives of both the parent (20d) and 10-methoxyl (21d) series had similar binding affinities and were both antagonists with similar potencies. The 11-methoxy-6,7-5H-benzo[c]azepino[2,1-a]indoles (25a-d) had higher binding affinities than the corresponding parent compounds (23a-d) at the MT2 receptor but similar affinities at the mt(1) site; all of the compounds were antagonists in the functional assay. Changing 11-methoxy for 11-ethoxy decreased the binding affinity slightly, and this was more evident at the MT2 receptor. All of the derivatives investigated had either the same or a greater affinity for the human MT2 receptor compared to the mt(1) receptor (range 1:1-1:132). This suggests that the mt(1) and MT2 receptor pockets differ in their ability to accommodate alkyl groups in the indole nitrogen region of the melatonin molecule. Two compounds (7c and 25c) were tested in functional assays on recombinant mt(1) and MT2 melatonin receptors. Compound 7c is a potent agonist with some selectivity (44-fold) for the MT2 receptor, while 25c is an MT2-preferring antagonist. Increasing the carbon chain length between N-1 of indole and the 2-phenyl group from n = 1 through n = 3 leads to a fairly regular decrease in the binding affinity, but, remarkably, when n = 3, it converts the methoxy compounds from melatonin agonists to antagonists. The Xenopus melatonin receptor thus cannot accommodate an N-n-alkyl chain attached to a 2-phenyl substituent with n > 2 in the required orientation to induce or stabilize the active receptor conformation.

  DOI：

  10.1021/jm980684+

文献信息

• A modular CuI-L-proline catalyzed one-pot route for the rapid access of constrained and privileged hetero-atom-linked medium-sized ring systems
  作者：Vunnam Srinivasulu、Kim D. Janda、Imad A. Abu-Yousef、Matthew John O'Connor、Taleb H. Al-Tel

  DOI：10.1016/j.tet.2017.02.061

  日期：2017.4

  4]diazepin, benzo[e]pyrrolo[1,2-a][1,4]diazocin, benzo[e]pyrido[1,2-a][1,4]diazocinones, dibenzo[b,f][1,5]diazoninones, dihydrodibenzo[b,e][1,4]thiazepine, dibenzo[b,e][1,4]thiazocine and benzo[6,7][1,4]diazepino[1,2-a]indole. Moreover, the synthetic procedures described herein, allows rapid entries to synthetically challenging medium-sized heterocyclic systems with good overall yields.

  开发了一种有效的CuI-L-脯氨酸催化的一锅合成方法，以生成一系列骨架多样的杂环系统，大小范围为6至9。该设计策略的显着特征是其使用S N 2反应的模块化合成效用。随后是微波辅助的CuI-L-脯氨酸杂芳基化反应，该化合物已获得一系列杂环骨架的访问权，其中包括：苯并[e]吡咯并[1,2-a] [1,4]二氮杂，苯并[e]吡咯并[1,2-a] [1,4]二唑啉，苯并[e]吡啶基[1,2-a] [1,4]重氮酮，二苯并[b，f] [1,5]重氮酮，二氢二苯并[b， e] [1,4] thiazepine，二苯并[b，e] [1,4]噻唑嗪和苯并[6,7] [1,4]二氮杂p [1,2- a]吲哚。此外，本文所述的合成方法允许以良好的总收率快速进入具有合成挑战性的中型杂环系统。
• Assessment of Double-Barrelled Heck Cyclizations as a Means for Construction of the 14-Phenyl-8,9-dihydro- 6H-[1]benzopyrano[4′,3′:4,5]pyrrolo[2,1-a]isoquinolin- 6-one Core Associated with Certain Members of the Lamellarin Class of Marine Natural Product
  作者：Martin G. Banwell、David C. R. Hockless、Bernard L. Flynn、Robert W. Longmore、David Rae

  DOI：10.1071/ch99021

  日期：——

  The 1,2,4-trisubstituted pyrrole (4), which is readily prepared from pyrrole itself, undergoes double- barrelled Heck cyclizations to give, inter alia, compounds (3) and (17) for which crystal structures have been determined. Product (3) constitutes the core associated with several key members, e.g. (1) and (2), of the lamellarin class of marine alkaloid.

  1,2,4-三取代的吡咯 (4) 很容易从吡咯本身制备出来。 经过双管 Heck 环化反应，除其他外，可得到化合物 (3) 和 (17)、 其中，化合物 (3) 和 (17) 的晶体结构已经确定。 晶体结构已经确定。产物 (3) 是与几个关键成员（如 (1)和(2)，构成了海洋生物碱中薄片素类的核心。 生物碱。
• Syntheses of a variety of lamellarin compounds and analogues
  申请人：The Australian National University

  公开号：US06469171B1

  公开（公告）日：2002-10-22

  The present invention relates to methods for preparing a variety of Lamellarin compounds and analogues via a synthetic intermediate, which methods involved the step of performing an intramolecular cyclization of a compound of Formula (I) to produce compounds of Formula(II), wherein the variables are given in the specification.

  本发明涉及通过合成中间体制备各种薄板素化合物和类似物的方法，所涉及的方法包括执行分子内环化步骤，将化合物(I)环化为产生化合物(II)，其中变量在规范中给出。
• Novel aminobenzoephenones
  申请人：——

  公开号：US20030119902A1

  公开（公告）日：2003-06-26

  The invention relates to a novel class of aminobenzophenones derivatives, to pharmaceutical preparations comprising said compounds, to dosage units of such preparations, to methods of treating patients comprising administering said compounds, and to the use of said compounds in the manufacture of pharmaceutical preparations.

  该发明涉及一种新型的氨基苯并酮衍生物类别，涉及包含该类化合物的药物制剂，涉及这种制剂的剂量单位，涉及包括给予该类化合物的治疗方法，以及涉及使用该类化合物制造药物制剂。
• Direct Synthesis of Pyrazolo[5,1‐ <i>a</i> ]isoindoles <i>via</i> Intramolecular Palladium‐Catalyzed CH Bond Activation
  作者：Young Lok Choi、Hyuk Lee、Bum Tae Kim、Kihang Choi、Jung‐Nyoung Heo

  DOI：10.1002/adsc.201000260

  日期：2010.10.9

  An efficient, direct synthesis of pyrazolo[5,1-a]isoindoles employing a palladium-catalyzed intramolecular CH bond activation of 1-(2-halobenzyl)pyrazoles has been developed. The use of lithium chloride (LiCl) was found to be essential in these reactions, to suppress further CH bond activation at the C-3 position of pyrazolo[5,1-a]isoindole, when C-3 is unsubstituted. This protocol can be applied to

  已经开发出一种有效的直接合成吡唑并[5，1- a ]异吲哚的方法，该方法利用钯催化的1-（2-卤代苄基）吡唑的分子内CH键活化作用。发现在这些反应中必须使用氯化锂（LiCl），以抑制当C-3未取代时在吡唑并[5,1- a ]异吲哚的C-3位置的进一步CH键活化。该方案可用于通过顺序的分子内和分子间CH键活化合成具有六元中心环系统的吡唑并[5,1- a ]异喹啉和完全取代的吡唑并[5,1- a ]异吲哚。