tert-butyl 4-(4-methyl-2-oxo-2H-chromen-7-yl)piperazine-1-carboxylate | 1004549-20-5

• 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-(4-methyl-2-oxo-2H-chromen-7-yl)piperazine-1-carboxylate
• 英文别名: Tert-butyl 4-(4-methyl-2-oxochromen-7-yl)piperazine-1-carboxylate
• CAS: 1004549-20-5
• 化学式: C₁₉H₂₄N₂O₄
• 分子量: 344.411
• InChiKey: LICMYLZJJANUCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(4-methyl-2-oxo-2H-chromen-7-yl)piperazine-1-carboxylate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 1,2,3,4,5-五苯基-1′-(二叔丁基膦)二茂铁 、 N-甲基二环己基胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 2-((1E,3E)-5-((E)-3,3-dimethyl-1-(6-(4-(4-methyl-3-((E)-2-(6-methyl-1,2,4,5-tetrazin-3-yl)vinyl)-2-oxo-2H-chromen-7-yl)piperazin-1-yl)-6-oxohexyl)indolin-2-ylidene)penta-1,3-dien-1-yl)-1,3,3-trimethyl-3H-indol-1-ium 2,2,2-trifluoroacetate
  参考文献：
  名称：

  生物正交连接激活的荧光 FRET 二联体

  摘要：

  本文提出了将蓝色可激发核心的优异的四嗪连接依赖性荧光性转变为生物学上优选的发射范围的概念。这种中继机制导致黄色/红色荧光性改善，同时光稳定性增加和大的表观斯托克斯位移。所提出的荧光二元组也用于多色单激发成像方案和 STED 成像。

  DOI：

  10.1002/anie.202111855
• 作为产物：
  描述：

  羟甲香豆素 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 97.0h， 生成 tert-butyl 4-(4-methyl-2-oxo-2H-chromen-7-yl)piperazine-1-carboxylate
  参考文献：
  名称：

  生物正交连接激活的荧光 FRET 二联体

  摘要：

  本文提出了将蓝色可激发核心的优异的四嗪连接依赖性荧光性转变为生物学上优选的发射范围的概念。这种中继机制导致黄色/红色荧光性改善，同时光稳定性增加和大的表观斯托克斯位移。所提出的荧光二元组也用于多色单激发成像方案和 STED 成像。

  DOI：

  10.1002/anie.202111855

文献信息

• A rapid and modified approach for C-7 amination and amidation of 4-methyl-7-nonafluorobutylsulfonyloxy coumarins under microwave irradiation
  作者：M. Nibin Joy、Yadav D. Bodke、K. K. Abdul Khader、M. Syed Ali Padusha、Ayyiliyath M. Sajith、A. Muralidharan

  DOI：10.1039/c4ra01720j

  日期：——

  A rapid approach for the synthesis of an array of 4-methyl-7-substituted coumarins has been developed.

  已开发出一种合成4-甲基-7-取代香豆素阵列的快速方法。
• FLUORESCENT SUBSTRATES FOR MONOAMINE TRANSPORTERS AS OPTICAL FALSE NEUROTRANSMITTERS
  申请人：of New York The Trustees of Columbia University in the City

  公开号：US20130190497A1

  公开（公告）日：2013-07-25

  The present invention relates to compounds of the general structure: wherein Y is O, X is O, bond α is absent and bond β is present, or Y is H, X is CH, bond α is present, and bond β is absent; atom Z is a carbon and bonds χ, δ and γ are present, or is a nitrogen and bonds χ, δ and γ are absent; R 1 is —H, —OH, —O—R 7 , —N(H)—R 8 , —N(H)—(CH 2 ) n —NH 2 , —N(R 9 )(R 10 ), or a piperazine cation; R 2 is either covalently bound to R 9 , or is —H, or is covalently bound to R 3 so as to form a substituted or unsubstituted pyrrole or R 2 is covalently bound to R 9 or R 8 or R 7 ; or R 1 and R 2 are covalently joined to form an aromatic ring; R 3 is either covalently bound to R 2 so as to form a pyrrole, or is, inter alia, —H, —OH, alkyl, or when Z is nitrogen R 3 is ═O; R 4 is, inter alia, —H, —OH, or —R 11 NH 2 ; R 5 is, inter alia, —H, —OH, or —R 12 NH 2 , and R 6 is either is covalently bound to R 10 or is —H, or R 6 is covalently bound to R 10 or R 8 or R 7 . This invention also provides processes for making the compounds as well as methods for monitoring activity of monoamine transporters or treating monoamine transporter-associated diseases by employing the compounds.

  本发明涉及以下通用结构的化合物：其中Y为O，X为O，键α不存在，键β存在，或Y为H，X为CH，键α存在，键β不存在；原子Z为碳并存在键χ，δ和γ，或为氮并不存在键χ，δ和γ；R1为—H，—OH，—O—R7，—N(H)—R8，—N(H)—(CH2)n—NH2，—N(R9)(R10)，或哌嗪阳离子；R2要么与R9共价结合，要么为—H，要么与R3共价结合以形成取代或未取代的吡咯，或R2与R9或R8或R7共价结合；或R1和R2共价结合以形成芳香环；R3要么与R2共价结合以形成吡咯，要么为—H，—OH，烷基，或者当Z为氮时，R3为═O；R4为—H，—OH，或—R11NH2；R5为—H，—OH，或—R12NH2，R6要么与R10共价结合，要么为—H，要么与R10或R8或R7共价结合。本发明还提供制备这些化合物的方法以及利用这些化合物监测单胺转运体活性或治疗单胺转运体相关疾病的方法。
• WO2008/13997
  申请人：——

  公开号：——

  公开（公告）日：——
• Catalytic Coupling of Arene C–H Bonds and Alkynes for the Synthesis of Coumarins: Substrate Scope and Application to the Development of Neuroimaging Agents
  作者：Paul A. Vadola、Dalibor Sames

  DOI：10.1021/jo3006842

  日期：2012.9.21

  C-H bond functionalization offers strategically novel approaches to complex organic compounds. However, many C-H functionalization reactions suffer from poor compatibility with Lewis basic functional groups, especially amines, which are often essential for biological activity. This study describes a systematic examination of the substrate scope of catalytic hydroarylation in the context of complex amino coumarin synthesis. The choice of substrates was guided by the design and development of the next generation of fluorescent false neurotransmitters (FFNs), neuroimaging probes we recently introduced for optical imaging of neurotransmission in the brain. Comparison of two mild protocols using catalytic PtCl4 or Au(PPh3)Cl/AgSbF6 revealed that each method has a broad and mutually complementary substrate scope. The relatively less active platinum system out-performed the gold catalyst with indole substrates lacking substitution at the C-3 position and provided higher regioselectivity in the case of carbazole-based substrates. On the other hand, the more active gold catalyst demonstrated excellent functional group tolerance, and the ability to catalyze the formation of strained, helical products. The development of these two protocols offers enhanced substrate scope and provides versatile synthetic tools required for the structure-activity examination of FFN neuroimaging probes as well as for the synthesis of complex coumarins in general.
• [EN] FLUORESCENT SUBSTRATES FOR MONOAMINE TRANSPORTERS AS OPTICAL FALSE NEUROTRANSMITTERS<br/>[FR] SUBSTRATS FLUORESCENTS DE TRANSPORTEURS DE MONOAMINES EN TANT QUE FAUX NEUROTRANSMETTEURS OPTIQUES
  申请人：UNIV COLUMBIA

  公开号：WO2008013997A2

  公开（公告）日：2008-01-31

  [EN] The present invention relates to compounds of the general structure: wherein Y is O, X is O, bond a is absent and bond ß is present, or Y is H, X is CH, bond a is present, and bond ß is absent; atom Z is a carbon and bonds ?, d and ? are present, or is a nitrogen and bonds ?, d and ? are absent; R₁ is -H, -OH, -O-R₇, -N(H) -R₈, -N (H) - (CH₂) _n-NH₂, -N(R₉) (R₁₀), or a piperazine cation; R₂ is either covalently bound to R₉, or is -H, or is covalently bound to R₃ so as to form a substituted or unsubstituted pyrrole or R₂ is covalently bound to R₉ or R₈ or R₇; or R₁ and R₂ are covalently joined to form an aromatic ring; R₃ is either covalently bound to R₂ so as to form a pyrrole, or is, inter alia, -H, -OH, alkyl, or when Z is nitrogen R₃ is =O; R₄ is, inter alia, -H, -OH, or -R₁₁NH₂; R₅ is, inter alia, -H, -OH, or -R₁₂NH₂, and R₆ is either is covalently bound to R₁₀ or is -H, or R₆ is covalently bound to R₁₀ or R₈ or R₇. This invention also provides processes for making the compounds as well as methods for monitoring activity of monoamine transporters or treating monoamine transporter-associated diseases by employing the compounds.
  [FR] L'invention porte sur des composés de formule générale (I) dans laquelle: Y est O, X est O, la liaison a est absente et la liaison ß est présente, ou Y est H, X est CH, la liaison a est présente, et la liaison ß est absent; l'atome Z est un carbone et les liaisons ?, d et ? sont présente, ou est azote et les liaisons ?, d et ? sont absentes; R1 est -H, -OH, -O-R7, -N(H) -R8, -N (H) - (CH2) n-NH2, -N(R9) (R10), ou un cation de pipérazine; R2 est soit lié par covalence à R9, ou est -H, ou est lié par covalence à R3 pour former un pyrrole substitué ou non substitué, ou R2 lié par covalence à R9 ou R8 ou R7; ou R1 et R2 sont liés par covalence pour former un cycle aromatique; R3 est soit lié par covalence à R2 former un pyrrole, ou est, entre autres, -H, -OH, alkyle, ou si Z est azote R3 est = O; R4 est, entre autres, -H, -OH, ou -R11NH2; R5 est, entre autres, -H, -OH, ou -R12NH2, et R6 est soit lié par covalence à R10 ou est -H, ou R6 est lié par covalence à R10 ou R8 ou R7. L'invention porte également sur le procédé d'élaboration desdits composés et sur des méthodes de surveillance de l'activité de transporteurs de monoamines, ou sur des méthodes de traitement de maladies associées aux transporteurs de monoamines par utilisation desdits composés.