1,2-dihydronaphtho<2,1-b>thiophene | 78076-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2-dihydronaphtho<2,1-b>thiophene
• 英文别名: Dihydronaphthothiophene；1,2-dihydrobenzo[e][1]benzothiole
• CAS: 78076-66-1
• 化学式: C₁₂H₁₀S
• 分子量: 186.277
• InChiKey: SROSVEYEPCTQMV-UHFFFAOYSA-N

物化性质

• 熔点：
  88-89 °C(Solv: water (7732-18-5); methanol (67-56-1))
• 沸点：
  336.9±12.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-dihydronaphtho<2,1-b>thiophene 在 四氯苯醌 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以86%的产率得到苯并[e][1]苯并二硫杂环戊烷
  参考文献：
  名称：

  深入了解苯并噻吩 C3-芳基化的好氧氧化 C-H/C-H 偶联中的区域选择性控制：迈向结构非传统 OLED 材料

  摘要：

  通过偶联反应安装含（苯并）噻吩的联芳基化合物已成为设计光电材料的主要方法。不可否认，两种（杂）芳烃之间的 C-H/C-H 交叉偶联反应将是通向这些结构片段的捷径。虽然更可靠的交叉偶联技术已经成熟以提供 C2 芳基化（苯并）噻吩，但芳基化 C3 位的有效方法仍未开发。在这里，我们深入了解了决定这些交叉偶联反应的区域选择性转换的因素。X 射线晶体学分析为三氟甲磺酸盐在区域选择性脱芳构化和醋酸盐在碱辅助抗芳烃中的关键作用提供了确凿的证据。-β-去质子化重构化。涉及两种底物的中型脱芳环金属化加合物的首次分离和 X 射线表征为有氧氧化 Ar-H/Ar-H 交叉偶联反应提供了额外的见解。机械突破孵化了第一个例子，使苯并噻吩的 C-H/C-H 型 C3-芳基化成为可能。最后，该化学物质用于设计具有螺旋构象的蓝色发射热激活延迟荧光 (TADF) 材料，在 OLED 中表现出高达 25.4% 的最大外部量子效率。

  DOI：

  10.1021/jacs.1c11277
• 作为产物：
  描述：

  萘并[2,1-b]噻吩-1-醇 在 氢氧化钾 、 一水合肼 作用下， 生成 1,2-dihydronaphtho<2,1-b>thiophene
  参考文献：
  名称：

  Friedel-Crafts Cyclization of ι-(α-Naphthyl)-1-alkanesulfonyl Chlorides¹

  摘要：

  DOI：

  10.1021/ja01632a017

文献信息

• Abdel-Wahab, Aboel-Magd A.; El-Khawaga, Ahmed M.; El-Zohry, Maher F., Phosphorus and Sulfur and the Related Elements, 1984, vol. 19, p. 31 - 44
  作者：Abdel-Wahab, Aboel-Magd A.、El-Khawaga, Ahmed M.、El-Zohry, Maher F.、Khalaf, Ali A.

  DOI：——

  日期：——
• A facile two-step synthesis of thiophene end-capped aromatic systems
  作者：Bunyarat Rungtaweevoranit、Akkarapol Butsuri、Krittaphat Wongma、Karoon Sadorn、Kitjanit Neranon、Chakkrapan Nerungsi、Tienthong Thongpanchang

  DOI：10.1016/j.tetlet.2012.01.122

  日期：2012.4

  Thiophene end-capped aromatic analogues, that is, naphthothiophenes, naphthodithiophenes, pyrenothiophene, and benzotrithiophene, can be prepared from commercially available hydroxyarenes in two steps, including (1) a consecutive acid-mediated nucleophilic aromatic substitution of hydroxyarenes with 2-mercaptoethanol, followed by cyclization to form an arene-fused dihydrothiophene, and (2) oxidation of the dihydrothiophene unit to thiophene. (C) 2012 Elsevier Ltd. All rights reserved.
• Clark, Peter David; McKinnon, David M., Canadian Journal of Chemistry, 1981, vol. 59, p. 227 - 231
  作者：Clark, Peter David、McKinnon, David M.

  DOI：——

  日期：——
• CLARK P. D.; MCKINNON D. M., CAN. J. CHEM., 1981, 59, NO 2, 227-231
  作者：CLARK P. D.、 MCKINNON D. M.

  DOI：——

  日期：——
• ANDROGEN RECEPTOR LIGANDS
  申请人：Lloyd David George

  公开号：US20140357682A1

  公开（公告）日：2014-12-04

  Non ligand binding pocket antagonists for the human androgen receptor. The androgen receptor (AR) is a member of the Nuclear Receptor (NR) family and its role is to modulate the biological effects of the endogenous androgens, testosterone (tes) and dihydrotestosterone (DHT). Synthetic androgens and anti-androgens have therapeutic value in the treatment of various androgen dependent conditions, from regulation of male fertility to prostate cancer. Current treatment of prostate cancer (PCa) typically involves administration of ‘classical’ antiandrogens, competitive inhibitors of natural AR ligands, DHT and tes, for the ligand binding pocket (LBP) in the C-terminal ligand binding domain (LBD) of the AR. However, prolonged LBP-targeting can often lead to androgen resistance and alternative therapies and therapeutic strategies are urgently required. Disclosed herein are a class of non-steroidal, small molecule AR antagonists which inhibit the transcriptional activity of the AR by non LBP-mediated modulation. The novel class reported demonstrates full (‘true’) antagonism in AR with low micromolar potency, high selectivity over both the Estrogen Receptors alpha and beta (ERα and ERβ) and the Glucocorticoid Receptor (GR) and only micromolar partial antagonism in the Progesterone Receptor (PR). Data provide compelling evidence for such non-LBP intervention as an alternative approach to classical PCa therapy. (Formula I).