tert-butyl-4-[6-(2,2-dicyano-1-methylvinyl)-2-naphthyl]-1-piperazinecarboxylate | 211109-15-8

• 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-[6-(2,2-dicyano-1-methylvinyl)-2-naphthyl]-1-piperazinecarboxylate
• 英文别名: tert-butyl 4-[6-(1,1-dicyanoprop-1-en-2-yl)naphthalen-2-yl]piperazine-1-carboxylate
• CAS: 211109-15-8
• 化学式: C₂₄H₂₆N₄O₂
• 分子量: 402.496
• InChiKey: IYWYTIJSHOGXLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl-4-[6-(2,2-dicyano-1-methylvinyl)-2-naphthyl]-1-piperazinecarboxylate 在 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.08h， 生成 2-[1-(6-piperazino-2-naphthyl)ethylidene]malononitrile
  参考文献：
  名称：

  Methods for binding agents to b-amyloid plaques

  摘要：

  提供了一种用于在体内或体外标记结构（如β-淀粉样斑块和神经原纤维缠结）的方法，包括将大脑组织与一个或多个化合物接触，最好是用正电子发射断层扫描（PET）检测的放射性标记。

  公开号：

  US20070053831A1
• 作为产物：
  描述：

  6-甲氧基-2-乙酰萘 在 吡啶 、 盐酸 、 sodium hydroxide 、 四丁基硫酸氢铵 、 sodium hydrogensulfite 作用下， 以 甲苯 为溶剂， 生成 tert-butyl-4-[6-(2,2-dicyano-1-methylvinyl)-2-naphthyl]-1-piperazinecarboxylate
  参考文献：
  名称：

  Functionalization of a viscosity-sensitive fluorophore for probing of biological systems

  摘要：

  Functionalization of a viscosity-sensitive visible wavelength fluorophore 2-(1,1-dicyanopropenyl-2)-6-dimethylaminonaphthalene (DDNP), with the intent to incorporate its favorable optical properties into a probe for structural and functional imaging by fluorescence microscopy, is described. Spiperone, a highly potent ligand for the dopamine D-2 receptors, was conjugated via an ethylpiperazine moiety to the fluorophore giving fluorescent probes that can be excited in the UV and Vis range. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00241-8
• 作为试剂：
  描述：

  tert-Butyl 4-(6-acetyl-2-naphthyl)-1-piperazinecarboxylate 、 丙二腈 、 在 silica 、 氯仿 、 tert-butyl-4-[6-(2,2-dicyano-1-methylvinyl)-2-naphthyl]-1-piperazinecarboxylate 作用下， 以 吡啶 为溶剂， 反应 18.17h， 以155 mg (77%) of tert-butyl-4-[6-(2,2-dicyano-1-methylvinyl)-2-naphthyl]-1-piperazinecarboxylate were obtained的产率得到tert-butyl-4-[6-(2,2-dicyano-1-methylvinyl)-2-naphthyl]-1-piperazinecarboxylate
  参考文献：
  名称：

  Methods for labeling &bgr;-amyloid plaques and neurofibrillary tangles

  摘要：

  一种用于体内和体外标记β-淀粉样斑块和神经原纤维缠结的方法，包括将式(I)化合物与哺乳动物组织接触。在式(I)中，R1选自由以下组成的群体：—C(O)-烷基，—C(O)-烷基亚烷基-R4，—C(O)O-烷基，—C(O)O-烷基亚烷基-R4，—C═C(CN)2-烷基，—C═C(CN)2-烷基亚烷基-R4，R4选自由以下组成的群体：烷基，取代烷基，芳基和取代芳基；R5选自由以下组成的群体：—NH2，—OH，—SH，—NH-烷基，—NHR4，—NH-烷基亚烷基-R4，—O-烷基，—O-烷基亚烷基-R4，—S-烷基和—S-烷基亚烷基-R4；R6选自由以下组成的群体：—CN，—COOH，—C(O)O-烷基，—C(O)O-烷基亚烷基-R4，—C(O)-烷基，—C(O)-烷基亚烷基-R4，—C(O)-卤素，—C(O)NH，—C(O)NH-烷基，—C(O)NH-烷基亚烷基-R4；R7选自由以下组成的群体：O，NH和S；R8为N，O或S。R2和R3各自独立选自由以下组成的群体：烷基和烷基亚烷基-R10，其中R10选自由以下组成的群体：—OH，—OTs，卤素，spiperone，spiperone ketal和spiperone-3-yl。或者，R2和R3共同形成一个杂环，可选地取代至少一个选自由以下组成的群体的基：烷基，烷氧基，OH，OTs，卤素，烷基亚烷基-R10，羰基，spiperone，spiperone ketal和spiperone-3-yl。在式(I)的化合物中，氢、卤素或碳原子中的一个或多个可以可选地被放射性标记替换。

  公开号：

  US06274119B1

文献信息

• Methods for binding agents to b-amyloid plaques
  申请人：Barrio R. Jorge

  公开号：US20070053831A1

  公开（公告）日：2007-03-08

  A method for labeling structures, such as β-amyloid plaques and neurofibrillary tangles, in vivo or in vitro, is provided and comprises contacting brain tissue with one or more compounds, preferably radiolabeled for detection by positron emission tomography (PET).

  提供了一种用于在体内或体外标记结构（如β-淀粉样斑块和神经原纤维缠结）的方法，包括将大脑组织与一个或多个化合物接触，最好是用正电子发射断层扫描（PET）检测的放射性标记。
• Compositions for labeling beta-amyloid plaques and neurofibrillary tangles
  申请人：——

  公开号：US20040072371A1

  公开（公告）日：2004-04-15

  Compositions useful for labeling &bgr;-amyloid plaques and neurofibrillary tangles are provided. The compositions comprises compounds of formula (I): 1 wherein R 1 is selected from the group consisting of —C(O)-alkyl, —C(O)-alkylenyl-R 4 , —C(O)O-alkyl, —C(O)O-alkylenyl-R 4 , —C═C(CN) 2 -alkyl, —C═C(CN) 2 -alkylenyl-R 4 , 2 wherein R 4 is a radical selected from the group consisting of alkyl, substituted alkyl, aryl and substituted aryl; R 5 is a radical selected from the group consisting of —NH 2 , —OH, —SH, —NH-alkyl, —NHR 4 , —NH-alkylenyl-R 4 , —O-alkyl, —O-alkylenyl-R 4 , —S-alkyl, and —S-alkylenyl-R 4 ; R 6 is a radical selected from the group consisting of —CN, —COOH, —C(O)O-alkyl, —C(O)O-alkylenyl-R 4 , —C(O)-alkyl, —C(O)-alkylenyl-R 4 , —C(O)-halogen, —C(O)NH-alkyl, —C(O)NH-alkylenyl-R 4 and —C(O)NH 2 ; R 7 is a radical selected from the group consisting of O, NH, and S; and R 8 is N, O or S; and R 2 is selected from the group consisting of alkyl and alkylenyl-R 10 and R 3 is alkylenyl-R 10 , wherein R 10 is selected from the group consisting of —OH, —OTs, halogen, spiperone, spiperone ketal, and spiperone-3-yl, or R 2 and R 3 together form a heterocyclic ring, optionally substituted with at least one radical selected from the group consisting of alkyl, alkoxy, OH, OTs, halogen, alkyl-R 10 , carbonyl, spiperone, spiperone ketal and spiperone-3-yl, and further wherein one or more of the hydrogen, halogen or carbon atoms are optionally replaced with a radiolabel.

  提供了用于标记&bgr;-淀粉样斑块和神经原纤维缠结的组合物。该组合物包括以下化合物(I)：1其中R1选自由—C(O)-烷基，—C(O)-烷基烯基-R4，—C(O)O-烷基，—C(O)O-烷基烯基-R4，—C═C(CN)2-烷基，—C═C(CN)2-烷基烯基-R4，2其中R4选自烷基，取代烷基，芳基和取代芳基中的一种基团；R5选自—NH2，—OH，—SH，—NH-烷基，—NHR4，—NH-烷基烯基-R4，—O-烷基，—O-烷基烯基-R4，—S-烷基和—S-烷基烯基-R4中的一种基团；R6选自—CN，—COOH，—C(O)O-烷基，—C(O)O-烷基烯基-R4，—C(O)-烷基，—C(O)-烷基烯基-R4，—C(O)-卤素，—C(O)NH-烷基，—C(O)NH-烷基烯基-R4和—C(O)NH2中的一种基团；R7选自O，NH和S；R8为N，O或S；R2选自烷基和烷基烯基-R10，R3为烷基烯基-R10，其中R10选自—OH，—OTs，卤素，斯皮罗隆，斯皮罗隆酮，和斯皮罗隆-3-基，或R2和R3一起形成一个杂环环，可选地取代至少一个选自烷基，烷氧基，OH，OTs，卤素，烷基-R10，羰基，斯皮罗隆，斯皮罗隆酮和斯皮罗隆-3-基的基团，进一步其中一个或多个氢，卤素或碳原子可选择用放射性标记取代。
• Methods for labeling beta-amyloid plaques and neurofibrillary tangles
  申请人：The Regents of the University of California

  公开号：US20020022002A1

  公开（公告）日：2002-02-21

  A method for labeling &bgr;-amyloid plaques and neurofibrillary tangles in vivo and in vitro, comprises contacting a compound of formula (I): 1 with mammalian tissue. In formula (I), R 1 is selected from the group consisting of —C(O)-alkyl, —C(O)-alkylenyl-R 4 , —C(O)O-alkyl, —C(O)O-alkylenyl-R 4 , —C═C(CN) 2 -alkyl, —C═C(CN) 2 -alkylenyl-R 4 , 2 R 4 is a radical selected from the group consisting of alkyl, substituted alkyl, aryl and substituted aryl; R 5 is a radical selected from the group consisting of —NH 2 , —OH, —SH, —NH-alkyl, —NHR 4 , —NH-alkylenyl-R 4 , —O-alkyl, —O-alkylenyl-R 4 , —S-alkyl, and —S-alkylenyl-R 4 ; R 6 is a radical selected from the group consisting of —CN, —COOH, —C(O)O-alkyl, —C(O)O-alkylenyl-R 4 , —C(O)-alkyl, —C(O)-alkylenyl-R 4 , —C(O)-halogen, —C(O)NH 2 , —C(O)NH-alkyl, —C(O)NH-alkylenyl-R 4 ; R 7 is a radical selected from the group consisting of O, NH, and S; and R 8 is N, O or S. R 2 and R 3 are each independently selected from the group consisting of alkyl and alkylenyl-R 10 , wherein R 10 is selected from the group consisting of —OH, —OTs, halogen, spiperone, spiperone ketal and spiperone-3-yl. Alternatively, R 2 and R 3 together form a heterocyclic ring, optionally substituted with at least one radical selected from the group consisting of alkyl, alkoxy, OH, OTs, halogen, alkylenyl-R 10 , carbonyl, spiperone, spiperone ketal and spiperone-3-yl. In the compounds of formula (I), one or more of the hydrogen, halogen or carbon atoms can, optionally, be replaced with a radiolabel.

  一种用于体内和体外标记β淀粉样斑块和神经原纤维缠结的方法，包括将式(I)的化合物1与哺乳动物组织接触。在式(I)中，R1选自由以下组成的群体：—C(O)-烷基，—C(O)-烷基亚烷基-R4，—C(O)O-烷基，—C(O)O-烷基亚烷基-R4，—C═C(CN)2-烷基，—C═C(CN)2-烷基亚烷基-R4，2R4选自由以下组成的基团：烷基，取代烷基，芳基和取代芳基；R5选自由以下组成的基团：—NH2，—OH，—SH，—NH-烷基，—NHR4，—NH-烷基亚烷基-R4，—O-烷基，—O-烷基亚烷基-R4，—S-烷基和—S-烷基亚烷基-R4；R6选自由以下组成的基团：—CN，—COOH，—C(O)O-烷基，—C(O)O-烷基亚烷基-R4，—C(O)-烷基，—C(O)-烷基亚烷基-R4，—C(O)-卤素，—C(O)NH2，—C(O)NH-烷基，—C(O)NH-烷基亚烷基-R4；R7选自由以下组成的基团：O，NH和S；R8是N，O或S。R2和R3各自独立地选自由以下组成的群体：烷基和亚烷基-R10，其中R10选自由以下组成的群体：—OH，—OTs，卤素，spiperone，spiperone ketal和spiperone-3-yl。或者，R2和R3一起形成一个杂环，可选地用以下至少一个基团取代：烷基，烷氧基，OH，OTs，卤素，亚烷基-R10，羰基，spiperone，spiperone ketal和spiperone-3-yl。在式(I)的化合物中，一个或多个氢、卤素或碳原子可以选择性地被放射性标记取代。
• Compositions for labeling β-amyloid plaques and neurofibrillary tangles
  申请人：Regents of University of California

  公开号：US07341709B2

  公开（公告）日：2008-03-11

  Compositions useful for labeling β-amyloid plaques and neurofibrillary tangles are provided. The compositions comprises compounds of formula (I): wherein R1 is selected from the group consisting of —C(O)-alkyl, —C(O)-alkylenyl-R4, —C(O)O-alkyl, —C(O)O-alkylenyl-R4, —C═C(CN)2-alkyl, —C═C(CN)2-alkylenyl-R4, wherein R4 is a radical selected from the group consisting of alkyl, substituted alkyl, aryl and substituted aryl; R5 is a radical selected from the group consisting of —NH2, —OH, —SH, —NH-alkyl, —NHR4, —NH-alkylenyl-R4, —O-alkyl, —O-alkylenyl-R4, —S-alkyl, and —S-alkylenyl-R4; R6 is a radical selected from the group consisting of —CN, —COOH, —C(O)O-alkyl, —C(O)O-alkylenyl-R4, —C(O)-alkyl, —C(O)-alkylenyl-R4, —C(O)-halogen, —C(O)NH-alkyl, —C(O)NH-alkylenyl-R4 and —C(O)NH2; R7 is a radical selected from the group consisting of O, NH, and S; and R8 is N, O or S; and R2 is selected from the group consisting of alkyl and alkylenyl-R10 and R3 is alkylenyl-R10, wherein R10 is selected from the group consisting of —OH, —OTs, halogen, spiperone, spiperone ketal, and spiperone-3-yl, or R2 and R3 together form a heterocyclic ring, optionally substituted with at least one radical selected from the group consisting of alkyl, alkoxy, OH, OTs, halogen, alkyl-R10, carbonyl, spiperone, spiperone ketal and spiperone-3-yl, and further wherein one or more of the hydrogen, halogen or carbon atoms are optionally replaced with a radiolabel.

  提供用于标记β-淀粉样斑块和神经原纤维缠结的组合物。该组合物包括式(I)的化合物：其中R1选自以下组的群：—C(O)-烷基，—C(O)-烷基亚烷基-R4，—C(O)O-烷基，—C(O)O-烷基亚烷基-R4，—C═C(CN)2-烷基，—C═C(CN)2-烷基亚烷基-R4，其中R4是选自以下组的基团：烷基，取代烷基，芳基和取代芳基；R5是选自以下组的基团：—NH2，—OH，—SH，—NH-烷基，—NHR4，—NH-烷基亚烷基-R4，—O-烷基，—O-烷基亚烷基-R4，—S-烷基和—S-烷基亚烷基-R4；R6是选自以下组的基团：—CN，—COOH，—C(O)O-烷基，—C(O)O-烷基亚烷基-R4，—C(O)-烷基，—C(O)-烷基亚烷基-R4，—C(O)-卤素，—C(O)NH-烷基，—C(O)NH-烷基亚烷基-R4和—C(O)NH2；R7是选自以下组的基团：O，NH和S；R8是N，O或S；R2选自以下组的群：烷基和烷基亚烷基-R10，R3是烷基亚烷基-R10，其中R10选自以下组的群：—OH，—OTs，卤素，斯皮罗隆，斯皮罗隆酮，和斯皮罗隆-3-基；或者R2和R3一起形成杂环环，可选地取代至少一个选自以下组的基团：烷基，烷氧基，OH，OTs，卤素，烷基-R10，羰基，斯皮罗隆，斯皮罗隆酮和斯皮罗隆-3-基，进一步地其中一个或多个氢，卤素或碳原子可选地被放射性标记取代。
• METHODS FOR BINDING AGENTS TO BETA-AMYLOID PLAQUES
  申请人：The Regents of the University of California

  公开号：EP1624900A2

  公开（公告）日：2006-02-15