2-(N,N-di-tert-butoxycarbonylamino)-7-chloro-4-methylbenzothiazole | 1115589-82-6

• 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-(N,N-di-tert-butoxycarbonylamino)-7-chloro-4-methylbenzothiazole
• 英文别名: tert-butyl N-(7-chloro-4-methyl-1,3-benzothiazol-2-yl)-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate
• CAS: 1115589-82-6
• 化学式: C₁₈H₂₃ClN₂O₄S
• 分子量: 398.911
• InChiKey: RWOGCXNTTNVYPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(N,N-di-tert-butoxycarbonylamino)-7-chloro-4-methylbenzothiazole 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 以83%的产率得到7-chloro-4-(dibromomethyl)-2-(N,N-di-tert-butoxycarbonylamino)benzothiazole
  参考文献：
  名称：

  Preparation of benzoheterocyclic carbaldeydes

  摘要：

  The preparation of benzoheterocyclic carbaldehydes in the 2-amino-substituted benzothiazole, benzoxazole and benzimidazole series is described. Starting with the methyl-substituted 2-aminobenzoheterocycle, the nitrogen is protected as an N,N-diBoc derivative. Next, free radical halogenation of the methyl group with NBS/AIBN affords the N(Boc)(2)-Protected benzylic dibromide which is directly used in the final step. A mild silver nitrite/dimethylsulfoxide-mediated conversion of the dibromide to the aldehyde functionality completes the process. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.066
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 7-氯-4-甲基苯并[d]噻唑-2-胺 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到2-(N,N-di-tert-butoxycarbonylamino)-7-chloro-4-methylbenzothiazole
  参考文献：
  名称：

  Preparation of benzoheterocyclic carbaldeydes

  摘要：

  The preparation of benzoheterocyclic carbaldehydes in the 2-amino-substituted benzothiazole, benzoxazole and benzimidazole series is described. Starting with the methyl-substituted 2-aminobenzoheterocycle, the nitrogen is protected as an N,N-diBoc derivative. Next, free radical halogenation of the methyl group with NBS/AIBN affords the N(Boc)(2)-Protected benzylic dibromide which is directly used in the final step. A mild silver nitrite/dimethylsulfoxide-mediated conversion of the dibromide to the aldehyde functionality completes the process. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.066

文献信息

• Preparation of benzoheterocyclic carbaldeydes
  作者：Frederick A. Luzzio、Marek T. Wlodarczyk

  DOI：10.1016/j.tetlet.2008.11.066

  日期：2009.2

  The preparation of benzoheterocyclic carbaldehydes in the 2-amino-substituted benzothiazole, benzoxazole and benzimidazole series is described. Starting with the methyl-substituted 2-aminobenzoheterocycle, the nitrogen is protected as an N,N-diBoc derivative. Next, free radical halogenation of the methyl group with NBS/AIBN affords the N(Boc)(2)-Protected benzylic dibromide which is directly used in the final step. A mild silver nitrite/dimethylsulfoxide-mediated conversion of the dibromide to the aldehyde functionality completes the process. (c) 2008 Elsevier Ltd. All rights reserved.