2-((thiophen-2-ylmethyl)thio)benzo[d]thiazole | 189579-62-2

• 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: 2-((thiophen-2-ylmethyl)thio)benzo[d]thiazole
• 英文别名: 2-(thiophen-2-ylmethylsulfanyl)-1,3-benzothiazole
• CAS: 189579-62-2
• 化学式: C₁₂H₉NS₃
• 分子量: 263.408
• InChiKey: BHSZYUPWABCLRW-UHFFFAOYSA-N

物化性质

• 沸点：
  421.7±47.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  94.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((thiophen-2-ylmethyl)thio)benzo[d]thiazole 在 sodium tungstate 、 双氧水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正庚烷 、 甲苯 为溶剂， 反应 2.18h， 生成 1,3-benzothiazol-2-yl (2-thienyl)fluoromethyl sulfone
  参考文献：
  名称：

  氟化苯并噻唑基砜的高产率合成：氟-朱里亚烯化反应的通用合成子。

  摘要：

  [反应：见正文]报道了用于合成氟烯烃的一般的高产率串联亲电氟化反应和改性的朱莉娅烯化反应。通过去质子氟化反应合成了一系列基于α-氟1,3-苯并噻唑-2-基砜的合成子。对于高产率氟化而言，至关重要的是非均相反应条件，因为在均相条件下仅回收了起始砜。将如此获得的α-氟1，3-苯并噻唑-2-基砜与各种醛和酮进行缩合反应，以提供高产率的区域特异性氟化烯烃。

  DOI：

  10.1021/ol060002+
• 作为产物：
  描述：

  2-氯甲基噻吩 、 2-巯基苯并噻唑 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以85%的产率得到2-((thiophen-2-ylmethyl)thio)benzo[d]thiazole
  参考文献：
  名称：

  实用的功能化烷基亚磺酸盐

  摘要：

  我们在此描述了脂肪族亚磺酸盐的三步合成。这种具有成本效益的方法涉及在温和条件下使用 2-巯基苯并噻唑，并表现出良好的产率（三个步骤高达 78%）。这种方法提供了获得各种功能化亚磺酸盐的途径。还注意到对不同官能团（烯烃、炔烃、醚、缩醛）的良好耐受性。

  DOI：

  10.1055/s-0036-1591588

文献信息

• Acidic-functionalized ionic liquid as an efficient, green, and metal-free catalyst for benzylation of sulfur, nitrogen, and carbon nucleophiles to benzylic alcohols
  作者：Xue-Qiang Chu、Ran Jiang、Yi Fang、Zheng-Yang Gu、Hua Meng、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1016/j.tet.2012.11.045

  日期：2013.1

  A series of HSO4- functionalized ILs was synthesized and used as efficient, green, and metal-free catalysts for benzylation. Notably, the catalytic system has wide substrate scopes and the ionic liquid catalysts were applied to investigate three different types of nucleophiles to give the desired benzylation products with moderate to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.
• Inhibition Of Superoxide Dismutase By Tetrathiomolybdate: Identification Of New Anti-Angiogenic And Antitumor Agents
  申请人：Mazar Andrew P.

  公开号：US20080031817A1

  公开（公告）日：2008-02-07

  Though copper is elevated in the tumor tissue and plasma of patients with various malignancies, the molecular targets for copper binding agents in angiogenesis and tumor progression remain poorly understood. It is disclosed that one anti-angiogenic target for the copper binding agent tetrathiomolybdate is intracellular CuZn-superoxide dismutase (SOD1). A second generation tetrathiomolybdate analog, ATN-224, inhibits endothelial cell (EC) proliferation in vitro, binds to SOD1 and inhibits its activity without displacing bound copper ATN-224 can accumulate in ECs and inhibit CuZnSOD activity with an IC 50 similar to the IC 50 for EC proliferation, resulting in increased generation of intracellular reactive oxygen species. Inhibition of EC proliferation by ATN-224 in vitro is substantially reversed by a synthetic porphyrin SOD mimetic. Similar results were observed in vivo, where inhibition of angiogenesis by ATN-224 in a Matrigel plug model was also reversed by MnTBAP. Thus, a distinct molecular target for copper depletion therapy has been identified and SOD1 is now validated as a target for anti-angiogenesis. Methods for screening, or designing, such SOD1 inhibitors for use as angiogenesis inhibitors and anti-cancer agents are disclosed.
• High-Yield Synthesis of Fluorinated Benzothiazolyl Sulfones:  General Synthons for Fluoro-Julia Olefinations
  作者：Arun K. Ghosh、Barbara Zajc

  DOI：10.1021/ol060002+

  日期：2006.4.1

  [reaction: see text] General, high-yield tandem electrophilic fluorination and modified Julia olefination for the synthesis of fluoro olefins is reported. A series of alpha-fluoro 1,3-benzothiazol-2-yl sulfone-based synthons were synthesized via deprotonation-fluorination. Of critical importance for high-yield fluorinations were heterogeneous reaction conditions, as under homogeneous conditions only

  [反应：见正文]报道了用于合成氟烯烃的一般的高产率串联亲电氟化反应和改性的朱莉娅烯化反应。通过去质子氟化反应合成了一系列基于α-氟1,3-苯并噻唑-2-基砜的合成子。对于高产率氟化而言，至关重要的是非均相反应条件，因为在均相条件下仅回收了起始砜。将如此获得的α-氟1，3-苯并噻唑-2-基砜与各种醛和酮进行缩合反应，以提供高产率的区域特异性氟化烯烃。
• A Practical Access to Functionalized Alkyl Sulfinates
  作者：M. Haddad、P. Phansavath、V. Ratovelomanana-Vidal、C. Tran、B. Flamme、A. Chagnes

  DOI：10.1055/s-0036-1591588

  日期：2018.7

  of aliphatic sulfinates. This cost-effective method involves the use of 2-mercaptobenzothiazole under mild conditions and exhibits good yields (up to 78% over three steps). This approach provides an access to a wide range of functionalized sulfinates. A good tolerance with respect to diverse functional groups (alkene, alkyne, ether, acetal) was also noted.

  我们在此描述了脂肪族亚磺酸盐的三步合成。这种具有成本效益的方法涉及在温和条件下使用 2-巯基苯并噻唑，并表现出良好的产率（三个步骤高达 78%）。这种方法提供了获得各种功能化亚磺酸盐的途径。还注意到对不同官能团（烯烃、炔烃、醚、缩醛）的良好耐受性。