4-(2,3-Dihydro-benzothiazol-2-yl)-phenol | 112946-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 4-(2,3-Dihydro-benzothiazol-2-yl)-phenol
• 英文别名: 4-(2,3-Dihydro-1,3-benzothiazol-2-yl)phenol
• CAS: 112946-91-5
• 化学式: C₁₃H₁₁NOS
• 分子量: 229.302
• InChiKey: LZLSKJZBPKUIAU-UHFFFAOYSA-N

物化性质

• 沸点：
  435.1±45.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,3-Dihydro-benzothiazol-2-yl)-phenol 在 对苯醌 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 4-(1,3-苯并噻唑-2-基)苯酚
  参考文献：
  名称：

  Two birds with one stone: redox co-production of 2-arylbenzothiazoles and hydroquinone

  摘要：

  A variety of 2-arylbenzothiazoles are co-produced with hydroquinone in the absence of additional reagents and catalysts under mild conditions. When this inherently waste-free process is employed, none of the reactions require the use of additional redox reagents, and all of them are environmentally friendly with excellent atom economy (>= 95%).

  DOI：

  10.1007/s00706-009-0231-6
• 作为产物：
  描述：

  2-氨基苯硫醇 、 对羟基苯甲醛 以 乙醇 为溶剂， 生成 4-(2,3-Dihydro-benzothiazol-2-yl)-phenol
  参考文献：
  名称：

  苯并噻唑啉作为高效还原剂对α-氨基酯的对映选择性有机催化转移加氢

  摘要：

  苯并噻唑啉用作手性磷酸催化的α-亚氨基酯转移加氢的有效和通用的还原剂。相应的α-氨基酯具有优异的对映选择性。还研究了带有羟基的新颖且易于除去的苯并噻唑啉。

  DOI：

  10.1002/adsc.201000328

文献信息

• Novel calcium antagonists. Synthesis and structure-activity relationship studies of benzothiazoline derivatives
  作者：Koji Yamamoto、Masanobu Fujita、Keizo Tabashi、Yoichi Kawashima、Eishin Kato、Masayuki Oya、Tadashi Iso、Junichi Iwao

  DOI：10.1021/jm00400a006

  日期：1988.5

  A series of novel compounds having a benzothiazoline skeleton was studied for their structure-activity relationship (SAR) with respect to Ca2+ antagonistic activity. As test compounds, analogues of 3-acyl-2-arylbenzothiazolines (3) were synthesized. Benzothiazoline derivatives (3) exerted higher Ca2+ antagonistic activity than the corresponding thiazolidine derivatives (2). Effects of substituents

  研究了一系列具有苯并噻唑啉骨架的新型化合物的相对于Ca2 +拮抗活性的结构活性关系（SAR）。作为测试化合物，合成了3-酰基-2-芳基苯并噻唑啉的类似物（3）。苯并噻唑啉衍生物（3）比相应的噻唑烷衍生物（2）具有更高的Ca2 +拮抗活性。研究了取代基R1-R4，氨基烷氧基和R2的取代位置以及亚甲基链的长度对生物活性的影响。化合物4 [3-乙酰基-2- [5-甲氧基-2- [4- [N-甲基-N-（3,4,5-三甲氧基苯乙基）氨基]丁氧基]苯基]苯并噻唑啉盐酸盐]显示出有效的Ca2 +拮抗活性体外对Langendorff灌注兔心脏中Na +向内快速通道和Ca2 +向内缓慢通道的双重抑制。
• Design, synthesis and evaluation of benzothiazole derivatives as multifunctional agents
  作者：Ernestine Nicaise Djuidje、Sabrina Sciabica、Raissa Buzzi、Valeria Dissette、Jan Balzarini、Sandra Liekens、Elena Serra、Elisa Andreotti、Stefano Manfredini、Silvia Vertuani、Anna Baldisserotto

  DOI：10.1016/j.bioorg.2020.103960

  日期：2020.8

  aetiology of various multifactorial diseases; on the other hand, the development of multifunctional compounds is a recognized strategy for the control of complex diseases. To this end, a series of benzothiazole derivatives was synthesized and evaluated for their multifunctional effectiveness as antioxidant, sunscreen (filter), antifungal and antiproliferative agents. Compounds were easily synthesized

  氧化应激是多种多因素疾病的产物或病因。另一方面，开发多功能化合物是控制复杂疾病的公认策略。为此，合成了一系列苯并噻唑衍生物并评估了其作为抗氧化剂，防晒霜（过滤剂），抗真菌剂和抗增殖剂的多功能功效。通过2-氨基硫酚与不同的苯甲醛之间的缩合反应可轻松合成化合物。SAR研究，特别是在苯并噻唑的2位和6位上，对4g和4k的鉴定为多功能药物设计中非常有趣的潜在化合物。特别是化合物4g是在HEK 293细胞中表达的hERG钾通道的最佳阻滞剂，具有60.32％的抑制作用，IC 50  = 4.79μM。
• Enantioselective Organocatalytic Transfer Hydrogenation of α‐Imino Esters by Utilization of Benzothiazoline as Highly Efficient Reducing Agent
  作者：Chen Zhu、Takahiko Akiyama

  DOI：10.1002/adsc.201000328

  日期：2010.10.9

  Benzothiazoline was employed as an efficient and versatile reducing agent for the chiral phosphoric acid-catalyzed transfer hydrogenation of α-imino esters. The corresponding α-amino esters were furnished with excellent enantioselectivities. Novel and readily removable benzothiazolines bearing a hydroxy group were also investigated.

  苯并噻唑啉用作手性磷酸催化的α-亚氨基酯转移加氢的有效和通用的还原剂。相应的α-氨基酯具有优异的对映选择性。还研究了带有羟基的新颖且易于除去的苯并噻唑啉。
• YAMAMOTO, KOJI;FUJITA, MASANOBU;TABASHI, KEIZO;KAWASHIMA, YOICHI;KATO, EI+, J. MED. CHEM., 31,(1988) N 5, 919-935
  作者：YAMAMOTO, KOJI、FUJITA, MASANOBU、TABASHI, KEIZO、KAWASHIMA, YOICHI、KATO, EI+

  DOI：——

  日期：——
• Two birds with one stone: redox co-production of 2-arylbenzothiazoles and hydroquinone
  作者：Guiyun Li、Yanqing Peng

  DOI：10.1007/s00706-009-0231-6

  日期：2010.1

  A variety of 2-arylbenzothiazoles are co-produced with hydroquinone in the absence of additional reagents and catalysts under mild conditions. When this inherently waste-free process is employed, none of the reactions require the use of additional redox reagents, and all of them are environmentally friendly with excellent atom economy (>= 95%).