6,7-dihydrobenzothien-4-yl trifluoromethanesulfonate | 148728-15-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 6,7-dihydrobenzothien-4-yl trifluoromethanesulfonate
• 英文别名: trifluoromethanesulfonic acid 4,5-dihydro-1-benzothiophene-4-yl ester；6,7-Dihydro-1-benzothiophen-4-yl trifluoromethanesulfonate
• CAS: 148728-15-8
• 化学式: C₉H₇F₃O₃S₂
• 分子量: 284.28
• InChiKey: WXWINUKBTWCTQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6,7-dihydrobenzothien-4-yl trifluoromethanesulfonate 在 palladium on activated charcoal 2,6-二叔丁基-4-甲基苯酚 、 叠氮磷酸二苯酯 、 potassium trimethylsilonate 、 四丁基氟化铵 、 氢气 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 25.0~150.0 ℃ 、344.73 kPa 条件下， 反应 311.25h， 生成 cis-4,5,5a,6,7,8,9,10-hexahydronaphtho<2,1-b>thiophen-9a(4H)-amine
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 4a-phenanthrenamine derivatives acting at the phencyclidine binding site of the N-methyl-D-aspartate receptor complex

  摘要：

  A novel series of octahydrophenanthrenamines and their heterocyclic analogues have been synthesized as potential noncompetitive antagonists of the N-methyl-D-aspartate (NMDA) receptor complex. The compounds were evaluated for their affinity at the phencyclidine (PCP) binding site by determining their ability to displace [H-3]TCP from crude rat brain synaptic membranes. A wide range of affinities were observed, with the most potent analogs possessing IC50's equivalent to that of the reference agent MK-801 (3,dizocilpine). NMDA antagonist activity was demonstrated by prevention of glutamate-induced accumulation of [Ca-45(2+)] in cultured rat cortical neurons. Selected compounds were also studied in vivo to determine their ability to prevent the lethal effects of systemically injected NMDA in the mouse. In general, the SAR of the phenanthrenamine series may be summarized as follows: (a) for the amino group at C4a, NHMe > NH2 > NHEt much-greater-than NC5H10; (b) for the B-ring substitution, X = CH2 > S > 0; (c) unsaturation of the C ring decreases receptor affinity; (d) cis-ring fusion between the B and C rings is desirable; (e) 6-hydroxy or 6-methoxy substitution of the phenanthrenamine system identified an additional hydrogen bonding interaction that substantially increased receptor affinity; (f) spiro analogues (such as 55, IC50 = 3400 nM), which altered the point of attachment of the C ring, caused a substantial reduction in PCP-site affinity. Molecules from this series were useful for refining a pharmacophore model consistent with previous models of the PCP site. In this model, the (R)-(+)-phenanthrenamine 13 superimposes closely onto MK-801 (3), and the angular 4a-amino group is believed to hydrogen bond with a putative receptor site atom. In the phenanthrenamine and thiaphenanthrenamine series, the (R)-(+)-enantiomers (9, 13, and 44) are more potent by approximately 5-10-fold than their corresponding (S)-(-)-enantiomers with respect to their affinity for the PCP site, their ability to prevent accumulation of [Ca-45(2+)] in cultured neuronal cells, and their protection against the lethal effects of NMDA in mice. In general, there was no separation between the dose that prevented NMDA lethality and the dose that produced ataxia in mice, except in the case of the thiaphenanthrenamines 41 and 43. We have not yet obtained evidence that this small separation in activity offers a therapeutic advantage in the treatment of cerebral ischemia or other neurodegenerative disorders.

  DOI：

  10.1021/jm00066a007
• 作为产物：
  描述：

  4,5,6,7-四氢-4-苯并噻吩 、 三氟甲磺酸酐 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 6,7-dihydrobenzothien-4-yl trifluoromethanesulfonate
  参考文献：
  名称：

  ERbeta配体。第5部分：一系列4'-羟基苯基-芳基-甲醛甲醛肟衍生物的合成和构效关系。

  摘要：

  制备了一系列的4'-羟基苯基-芳基-甲醛肟（5b），发现对雌激素受体-β（ERbeta）具有高亲和力（4nM）和适度的选择性（39倍）。基于这些新型配体的支架核心环之一的取代进一步扩展了我们的知识，以寻求对ERbeta的高亲和力和选择性。结构11的X射线共晶体表明，肟部分正在模仿染料木黄酮的C环，正如之前通过SAR和对接研究所预测的那样。

  DOI：

  10.1016/j.bmcl.2006.11.066

文献信息

• Electrocyclization of cis-dienals in organic synthesis: a new and versatile synthetic method for the preparation of aryl- and heteroaryl-fused coumarins
  作者：Yung-Son Hon、Tze-Wei Tseng、Chia-Yi Cheng

  DOI：10.1039/b912887e

  日期：——

  Benzo-, furo-, thieno-, and pyrido[f]coumarins were prepared by generating the 2H-pyran-2-one moieties from the oxidation of the corresponding 2H-pyran rings, which were formed in situ from the electrocyclization of cis-dienals.

  通过从相应的2H-吡喃环的氧化反应生成2H-吡喃-2-酮部分来制备苯并，呋喃-，噻吩并-和吡啶并[f]香豆素，它们是由顺式C-环的电环化而形成的。日记。
• Carbonyl 1,2-transposition through triflate-mediated α-amination
  作者：Zhao Wu、Xiaolong Xu、Jianchun Wang、Guangbin Dong

  DOI：10.1126/science.abl7854

  日期：2021.11.5

  Chemists devote tremendous effort to the precise placement of oxygens in molecular frameworks. Wu et al . report a convenient method to shift the oxygen in a carbonyl group to an adjacent carbon center. After activation of the oxygen to an alkenyl triflate, cooperative catalysis by palladium and norbornene adds nitrogen to the neighboring carbon while displacing the triflate with hydride. Hydrolysis then produces the desired shifted ketone. The protocol is well suited to late-stage variation of complex molecules during drug optimization. —JSY

  标题：酮转移的谨慎编排 化学家们致力于在分子框架中精确放置氧原子。吴等人报告了一种方便的方法，将羰基中的氧转移到相邻的碳中心。在将氧活化为烯基三氟乙酸酯后，钯和环辛烯的协同催化作用在邻近碳上加入氮，同时用氢化物取代三氟乙酸酯。然后水解产生所需的转移酮。该协议非常适合在药物优化期间对复杂分子进行后期变异。 —JSY
• Aryl-carbaldehyde oxime derivatives and their use as estrogenic agents
  申请人：Mewshaw Eric Richard

  公开号：US20070043077A1

  公开（公告）日：2007-02-22

  This invention provides estrogen receptor modulators having the structure where R 1 —R 5 are defined in the specification; or a pharmaceutically acceptable salt thereof.

  这项发明提供了具有以下结构的雌激素受体调节剂，其中R1-R5在说明书中定义；或其药学上可接受的盐。
• Polycyclic amines useful as cerebrovascular agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0388977A2

  公开（公告）日：1990-09-26

  A novel series of polycyclic amine derivatives, of formula I methods of making the compounds, novel intermediates, compositions containing them, and pharmaceutical compositions useful in the treatment and prevention of cerebrovascular disorders and useful as anesthetics or analgesics.

  式 I 的一系列新型多环胺衍生物 制造这些化合物的方法、新型中间体、含有这些化合物的组合物，以及用于治疗和预防脑血管疾病和用作麻醉剂或镇痛剂的药物组合物。
• α₂ Adrenoceptor Agonists as Potential Analgesic Agents. 2. Discovery of 4-(4-Imidazo)-1,3-dimethyl-6,7-dihydrothianaphthene as a High-Affinity Ligand for the α_2D Adrenergic Receptor
  作者：Tina M. Ross、Michele C. Jetter、Mark E. McDonnell、Robert E. Boyd、Charlene D. Connelly、Rebecca P. Martinez、Martin A. Lewis、Ellen E. Codd、Robert B. Raffa、Allen B. Reitz

  DOI：10.1021/jm990569e

  日期：2000.3.1