tert-butyl 4-(2-iodophenyl)piperazine-1-carboxylate | 1609659-20-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: tert-butyl 4-(2-iodophenyl)piperazine-1-carboxylate
• 英文别名: tert-butyl 4-(2-iodophenyl)piperazinecarboxylate
• CAS: 1609659-20-2
• 化学式: C₁₅H₂₁IN₂O₂
• 分子量: 388.248
• InChiKey: OYDHERCLKUCURA-UHFFFAOYSA-N

物化性质

• 沸点：
  427.0±40.0 °C(Predicted)
• 密度：
  1.481±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  32.78
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(2-iodophenyl)piperazine-1-carboxylate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium tert-butylate 、 potassium acetate 、 双(2-二苯基磷苯基)醚 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 18.34h， 生成
  参考文献：
  名称：

  11C-labeling and preliminary evaluation of vortioxetine as a PET radioligand

  摘要：

  Vortioxetine is a new multi-modal drug against major depressive disorder with high affinity for a range of different serotonergic targets in the CNS. We report the C-11-labeling of vortioxetine with [C-11] MeI using a Suzuki-protocol that allows for the presence of an unprotected amine. Preliminary evaluation of [C-11] vortioxetine in a Danish Landrace pig showed rapid brain uptake and brain distribution in accordance with the pharmacological profile, all though an unexpected high binding in cerebellum was also observed. [C-11] vortioxetine displayed slow tracer kinetics with peak uptake after 60 min and with limited wash-out from the brain. Further studies are needed but this radioligand may prove to be a valuable tool in unraveling the clinical effects of vortioxetine. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.044
• 作为产物：
  描述：

  N-Boc-哌嗪 在 N-碘代丁二酰亚胺 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 25.0h， 生成 tert-butyl 4-(2-iodophenyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Synthesis of ortho-Haloaminoarenes by Aryne Insertion of Nitrogen–Halide Bonds

  摘要：

  A rapid and general access to ortho-haloaminoarenes has been developed by aryne insertion into N-chloramine, N-bromoamine, and N-iodoamine bonds via two complementary protocols harnessing fluoride-promoted 1,2-elimination of ortho-trimethylsilyl aryltriflates. Typically, electron-deficient N-chloramines effectively react with aryne intermediates generated at elevated temperature with CsF, while less stable N-haloamines are found more efficient under milder, TBAF-mediated aryne formation at room temperature. Both protocols demonstrate a good level of regioselectivity and functional group tolerance. Efforts to elucidate the mechanism of NX insertion are also discussed. The practical value of this transformation is highlighted by rapid synthesis of novel analogues of the antipsychotic cariprazine.

  DOI：

  10.1021/jo502541t

文献信息

• Redox-active benzimidazolium sulfonamides as cationic thiolating reagents for reductive cross-coupling of organic halides
  作者：Weigang Zhang、Mengjun Huang、Zhenlei Zou、Zhengguang Wu、Shengyang Ni、Lingyu Kong、Youxuan Zheng、Yi Wang、Yi Pan

  DOI：10.1039/d0sc06446g

  日期：——

  Redox-active benzimidazolium sulfonamides as thiolating reagents have been developed for reductive C–S bond coupling. The IMDN-SO2R reagent provides a bench-stable cationic precursor to generate a portfolio of highly active N–S intermediates, which can be successfully applied in cross-electrophilic coupling with various organic halides. The employment of an electrophilic sulfur source solved the problem

  已开发出具有氧化还原活性的苯并咪唑磺酰胺作为硫醇化试剂用于还原 C-S 键偶联。IMDN-SO 2 R 试剂提供了一种稳定的阳离子前体，可生成一系列高活性 N-S 中间体，可成功应用于与各种有机卤化物的交叉亲电偶联。采用亲电硫源解决了催化剂失活问题，避免了硫醇的异味，具有条件实用、底物范围广、耐受性好等特点。