2-(1-氯乙基)-1,3-苯并噻唑 | 110704-27-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-(1-氯乙基)-1,3-苯并噻唑
• 英文名称: 2-(1-chloroethyl)benzothiazole
• 英文别名: 2-(1-Chlor-aethyl)-benzothiazol；1-(2-Benzothiazolyl)ethyl chloride；2-(1-Chloroethyl)-1,3-benzothiazole
• CAS: 110704-27-3
• 化学式: C₉H₈ClNS
• 分子量: 197.688
• InChiKey: RZSLIFPQFDTXPX-UHFFFAOYSA-N

物化性质

• 沸点：
  115-116 °C(Press: 4 Torr)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(1-氯乙基)-1,3-苯并噻唑 在 t-butoxide 作用下， 以 叔丁醇 为溶剂， 以64%的产率得到2-甲基-2H-1,4-苯并噻嗪-3(4H)-酮
  参考文献：
  名称：

  氯烷基苯并噻唑与醇盐的反应

  摘要：

  2-氯烷基苯并噻唑1a-c与醇盐反应生成取代基并进行环扩产物3和4。取代环的扩大竞争很大程度上取决于溶剂，在醇中优选取代反应，而在DMF中则优选环扩大。

  DOI：

  10.1016/s0040-4020(97)00243-3
• 作为产物：
  描述：

  2-羟甲基苯并噻唑 在 氯化亚砜 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 生成 2-(1-氯乙基)-1,3-苯并噻唑
  参考文献：
  名称：

  2-Benzothiazolylchloromethyllithium: Synthesis of oxiranes

  摘要：

  Deprotonation of 2-chloromethylbenzothiazole 1 with lithium diisopropylamide (LDA) in tetrahydrofuran (THF) at -78-degrees-C gives a red solution of 2-benzothiazolylchloromethyllithium 2, which couples with carbonyl compounds furnishing oxiranes 3.

  DOI：

  10.1016/s0040-4039(00)74787-3

文献信息

• Vicarious Nucleophilic Substitution of (Chloroalkyl)heterocycles with Nitroarenes
  作者：Saverio Florio、Patrizia Lorusso、Renzo Luisi、Catia Granito、Ludovico Ronzini、Luigino Troisi

  DOI：10.1002/ejoc.200300806

  日期：2004.5

  The vicarious nucleophilic substitution of potassium carbanions of the (chloromethyl)pyridines 1a and 1b, (chloromethyl)benzothiazole 1c, (chloromethyl)thiazole 1d, (chloroethyl)thiazole 1e and (chloroethyl)benzothiazole 1f with nitroarenes, leading to nitrobenzyl heterocycles 2 and 4−14 has been studied. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  （氯甲基）吡啶 1a 和 1b、（氯甲基）苯并噻唑 1c、（氯甲基）噻唑 1d、（氯乙基）噻唑 1e 和（氯乙基）苯并噻唑 1f 的钾碳负离子与硝基芳烃的替代亲核取代，导致硝基苄基 4 杂环 2 和-14 已被研究。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Novel, potent aldose reductase inhibitors: 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl]-1-phthalazineacetic acid (zopolrestat) and congeners
  作者：Banavara L. Mylari、Eric R. Larson、Thomas A. Beyer、William J. Zembrowski、Charles E. Aldinger、Michael F. Dee、Todd W. Siegel、David H. Singleton

  DOI：10.1021/jm00105a018

  日期：1991.1

  unrecognized binding site on the aldose reductase (AR) enzyme with strong affinity for benzothiazoles was pursued for the design of novel, potent aldose reductase inhibitors (ARIs). The first application of this hypothesis led to a novel series of 3,4-dihydro-4-oxo-3-(benzothiazolylmethyl)-1-phthalazineacetic+ + + acids. The parent of this series (207) was a potent inhibitor of AR from human placenta (IC50

  为了设计新型有效的醛糖还原酶抑制剂（ARI），人们寻求了一个新的工作假设，即在醛糖还原酶（AR）酶上具有迄今无法识别的结合位点，该结合位点对苯并噻唑具有很强的亲和力。该假设的首次应用产生了一系列新的3,4-二氢-4-氧代-3-（苯并噻唑基甲基）-1-酞嗪乙酸+ + +酸。该系列的母体（207）是一种有效的人胎盘AR抑制剂（IC50 = 1.9 x 10（-8）M），在糖尿病合并症的急性试验中，口服有效预防山楂醇在大鼠坐骨神经中的蓄积（ ED50 ＝ 18.5mg / kg）。通过药物化学原理（包括与其他药物系列的比喻）优化该线索，导致产生更有效的207同类药物，并最终设计出3，4-二氢-4-氧代-3-[[[5-（三氟甲基）-2-苯并噻唑基]甲基] -1-酞嗪乙酸（216，CP-73,850，zopolrestat）。在体外和体内，Zopolrestat被发现比207更有效。在急性试验中，其针对AR和ED50的IC50分别为3
• Heterocyclic oxophthalazinyl acetic acids
  申请人：Pfizer Inc.

  公开号：US04939140A1

  公开（公告）日：1990-07-03

  A heterocyclic oxophthalazinyl acetic acid having aldose reductast inhibitory activity of the formula ##STR1## wherein X is oxygen or sulfur; Z is a covalent bond, O, S, NH or CH.sub.2 or CHR.sub.5 Z is vinyl; R.sub.1 is hydroxy, or a prodrug group; R.sub.2 is a heterocyclic group, R.sub.3 and R.sub.4 are hydrogen or the same or a different substituent, and R.sub.5 is hydrogen, methyl or trifluoromethyl. The pharmaceutically acceptable acid addition salts of the above compounds wherein R.sub.1 is di(C.sub.1 -C.sub.4)alkylamino or (C.sub.1 -C.sub.4)alkoxy substituted by N-morpholino or di(C.sub.1 -C.sub.4)alkylamino and the pharmaceutically active base addition salts of the above compounds wherein R.sub.1 is hydroxy are also aldose reductase inhibitors.

  一种具有醛糖还原酶抑制活性的杂环氧酞嗪基乙酸，化学式为##STR1##其中X为氧或硫；Z为共价键，O，S，NH或CH.sub.2或CHR.sub.5，Z为乙烯基；R.sub.1为羟基或前药基团；R.sub.2为杂环基，R.sub.3和R.sub.4为氢或相同或不同的取代基，R.sub.5为氢，甲基或三氟甲基。上述化合物的药学可接受的酸盐，其中R.sub.1为二(C.sub.1-C.sub.4)烷基氨基或被N-吗啉基取代的(C.sub.1-C.sub.4)烷氧基，以及上述化合物的药学活性碱盐，其中R.sub.1为羟基，也是醛糖还原酶抑制剂。
• Chemoselective construction of novel steroid derivatives
  作者：Luigino Troisi、Saverio Florio、Catia Granito

  DOI：10.1016/s0039-128x(02)00032-6

  日期：2002.7

  alpha-Halo-alpha-heteroarylalkyllithiums, generated by deprotonation of the corresponding halides, when added promptly to steroids with C=O or C=NR groups, lead to epoxides and aziridines. The reactions are regio- and stereoselective; in fact, in the presence of more than one C=O group, the oxido or aziridino functions are formed uniquely at the C=O of C-17 (or C-20 depending on its position in the starting molecule), and the C-20(R) stereoisomer is often the only product isolated. Protection of the hydroxyl group present on several considered steroids was required, and it was accomplished through derivatization in acetyl, ether, or lactone. (C) 2002 Elsevier Science Inc. All rights reserved.
• Stereoselective synthesis of heterosubstituted aziridines and their functionalization
  作者：Luisella De Vitis、Saverio Florio、Catia Granito、Ludovico Ronzini、Luigino Troisi、Vito Capriati、Renzo Luisi、Tullio Pilati

  DOI：10.1016/j.tet.2003.11.056

  日期：2004.1

  Lithiated (alpha-chloroalkyl)heterocycles, generated by deprotonation with LDA at -78 degreesC in THF, add to various enantiopure imines affording 'one pot' chiral heterosubstituted aziridines in a diastereoselective manner. Lithiated heterosubstituted aziridines, obtained by deprotonation of the corresponding aziridines with n-BuLi at -78 degreesC in THF, were trapped by electrophiles (D2O or CH3I) with high stereoselectivity. (C) 2003 Elsevier Ltd. All rights reserved.