12-benzyl-8-hydroxy-2-(4-hydroxybenzyl)-11H-benz[f]imidazo[1,2-a]quinoxalin-3-one | 114496-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 12-benzyl-8-hydroxy-2-(4-hydroxybenzyl)-11H-benz[f]imidazo[1,2-a]quinoxalin-3-one
• 英文别名: coelenterazine-v；coelenterazine-ν；v-CTZ；16-benzyl-5-hydroxy-13-[(4-hydroxyphenyl)methyl]-11,14,17-triazatetracyclo[8.7.0.02,7.011,15]heptadeca-1(10),2(7),3,5,8,13,15-heptaen-12-one
• CAS: 114496-03-6
• 化学式: C₂₈H₂₁N₃O₃
• 分子量: 447.493
• InChiKey: NYDHAUJMUKSJRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  91.14
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-amino-3-phenylpropanenitrile 在 亚硝酸丁酯 、 硫酸 、 potassium tert-butylate 、 三溴化硼 、 N,N'-二环己基碳二亚胺 作用下， 生成 12-benzyl-8-hydroxy-2-(4-hydroxybenzyl)-11H-benz[f]imidazo[1,2-a]quinoxalin-3-one
  参考文献：
  名称：

  NOVEL COELENTERAZINE COMPOUNDS AND METHODS OF USE

  摘要：

  钙反应光蛋白是一类自发发光的蛋白质，与钙接触时会发出光。荧光蛋白是一种小型蛋白质，当受到光的激发时会改变光的颜色。荧光蛋白和钙活化光蛋白可以通过直接应用于观众、环境、演员或喷洒在设置中（如新型4D电影）来增强、令人惊叹、震撼、惊艳并提供娱乐效果。本发明涉及新型荧光素化合物及其使用方法，包括一种简单的输送装置，可将光蛋白输送到含有钙的表面上，通过其与钙的反应产生独特的、新颖的电影、戏剧、舞台、音乐会光学效果，这是一种娱乐性的新用途。钙普遍存在于大多数表面和环境中，正是这种钙的独特性质使得光蛋白在娱乐方面具有新颖的应用价值。

  公开号：

  US20170217969A1

文献信息

• PROCESS FOR PRODUCING v-COELENTERAZINE COMPOUNDS
  申请人：INOUYE Satoshi

  公开号：US20120232272A1

  公开（公告）日：2012-09-13

  A simple process for producing v-coelenterazine compounds has been desired. Described is a process for producing a v-coelenterazine compound represented by general formula (II) comprising (1) the step of reacting a compound of general formula (VIII) with a methyltriphenylphosphonium salt in the presence of a base to give a compound represented by general formula (IX), (2) the step of performing a ring-closing metathesis reaction on any one selected from the group consisting of the compound represented by general formula (IX) and a compound of general formula (X) which is the compound of general formula (IX) wherein the amino is protected with R 5 , and then deprotecting R 4 and, if any, R 5 to give a v-coelenteramine compound represented by general formula (XIV), and (3) the step of reacting the compound of general formula (XIV) with a compound represented by general formula (XV) to give the compound of general formula (II).

  已经需要一种生产v-虫螨菌素化合物的简单过程。描述了一种生产由通式（II）表示的v-虫螨菌素化合物的过程，包括（1）在碱存在下将通式（VIII）的化合物与甲基三苯基膦盐反应以得到通式（IX）表示的化合物的步骤，（2）在由通式（IX）表示的化合物和通式（X）的化合物中选择一个进行环闭合亚甲基交换反应的步骤，其中通式（X）是通式（IX）的化合物，其中氨基用R5保护，然后去保护R4和如有的话，R5，以得到由通式（XIV）表示的v-虫螨胺化合物，（3）将通式（XIV）的化合物与由通式（XV）表示的化合物反应以得到通式（II）的化合物。
• Process for producing benzo[f]quinoxaline compounds
  申请人：Inouye Satoshi

  公开号：US08772484B2

  公开（公告）日：2014-07-08

  A simple process for producing v-coelenterazine compounds has been desired. Described is a process for producing a v-coelenterazine compound represented by general formula (II) comprising (1) the step of reacting a compound of general formula (VIII) with a methyltriphenylphosphonium salt in the presence of a base to give a compound represented by general formula (IX), (2) the step of performing a ring-closing metathesis reaction on any one selected from the group consisting of the compound represented by general formula (IX) and a compound of general formula (X) which is the compound of general formula (IX) wherein the amino is protected with R5, and then deprotecting R4 and, if any, R5 to give a v-coelenteramine compound represented by general formula (XIV), and (3) the step of reacting the compound of general formula (XIV) with a compound represented by general formula (XV) to give the compound of general formula (II).

  一种简单的制备V-辣根蛋白酶化合物的方法已经被期望。本文描述了一种制备V-辣根蛋白酶化合物的方法，其包括：（1）在碱的存在下，将通式（VIII）的化合物与甲基三苯基膦盐反应，得到通式（IX）的化合物；（2）对通式（IX）的化合物或通式（IX）中氨基被R5保护的通式（X）的化合物中的任意一个进行环闭合的交叉烯烃反应，然后去除R4和R5（如果有），得到通式（XIV）的V-辣根胺化合物；（3）将通式（XIV）的化合物与通式（XV）的化合物反应，得到通式（II）的化合物。
• PROCESS FOR PRODUCING V-COELENTERAZINE COMPOUNDS
  申请人：JNC CORPORATION

  公开号：US20150119575A1

  公开（公告）日：2015-04-30

  A simple process for producing ν-coelenterazine compounds has been desired. The invention provides a process for producing a ν-coelenterazine compound represented by general formula (II) which comprises (1) the step of reacting a compound represented by general formula (VIII) with a methyltriphenylphosphonium salt in the presence of a base to give a compound represented by general formula (IX), (2) the step of performing a ring-closing metathesis reaction on any one selected from the group consisting of the compound represented by general formula (IX) and a compound represented by general formula (X) which is the compound represented by general formula (IX) wherein the amino is protected with R 5 , and then deprotecting R 4 and, if any, R 5 to give a ν-coelenteramine compound represented by general formula (XIV), and (3) the step of reacting the compound represented by general formula (XIV) with a compound represented by general formula (XV) to give the compound represented by general formula (II).

  生产ν-光珊瑚蛋白酶素化合物的简单过程一直是人们所期望的。本发明提供了一种生产由通式（II）表示的ν-光珊瑚蛋白酶素化合物的方法，该方法包括以下步骤：（1）在碱的存在下，将由通式（VIII）表示的化合物与甲基三苯基膦盐反应，得到由通式（IX）表示的化合物；（2）在由通式（IX）表示的化合物和由R5保护的通式（X）表示的化合物（其中氨基被保护）中选择任意一个化合物，进行环闭合的交换反应，然后去除R4和R5（如果有的话），得到由通式（XIV）表示的ν-光珊瑚蛋白酶胺化合物；（3）将由通式（XIV）表示的化合物与由通式（XV）表示的化合物反应，得到由通式（II）表示的化合物。
• Process for producing substituted benzo[F]imidazo[1,2-A]quinoxalin-3(11H)-ones
  申请人：JNC Corporation

  公开号：US08975403B2

  公开（公告）日：2015-03-10

  A simple process for producing v-coelenterazine compounds has been desired. Described is a process for producing a v-coelenterazine compound represented by general formula (II) comprising (1) the step of reacting a compound of general formula (VIII) with a methyltriphenylphosphonium salt in the presence of a base to give a compound represented by general formula (IX), (2) the step of performing a ring-closing metathesis reaction on any one selected from the group consisting of the compound represented by general formula (IX) and a compound of general formula (X) which is the compound of general formula (IX) wherein the amino is protected with R5, and then deprotecting R4 and, if any, R5 to give a v-coelenteramine compound represented by general formula (XIV), and (3) the step of reacting the compound of general formula (XIV) with a compound represented by general formula (XV) to give the compound of general formula (II).

  期望有一个简单的生产v-虫萤光素化合物的过程。本文描述了一种生产v-虫萤光素化合物的过程，该化合物由通式（II）表示，包括（1）将通式（VIII）的化合物与甲基三苯基膦盐在碱存在下反应，得到通式（IX）表示的化合物；（2）在通式（IX）表示的化合物和通式（X）的化合物中选择任意一种进行环闭合的交换反应，其中通式（X）的化合物是通式（IX）的化合物，其中氨基受到R5保护，然后去除R4和（如有）R5的保护基，得到通式（XIV）表示的v-虫萤胺化合物；（3）将通式（XIV）表示的化合物与通式（XV）表示的化合物反应，得到通式（II）表示的化合物。
• Concise Synthesis of <i>v</i>-Coelenterazines
  作者：Takamitsu Hosoya、Rie Iimori、Suguru Yoshida、Yuto Sumida、Yuiko Sahara-Miura、Jun-ichi Sato、Satoshi Inouye

  DOI：10.1021/acs.orglett.5b01872

  日期：2015.8.7

  A novel synthetic method for v-coelenterazine (v-CTZ), which is a vinylene-bridged analog of native CTZ with a large red-shifted luminescence property, is described. The synthesis was achieved in a concise way through the use of three sequential cross-coupling reactions and ring-closing metathesis (RCM). A newly synthesized C2-modified trifluoromethyl analog cf3-v-CTZ showed slightly more red-shifted luminescence than v-CTZ when it was used as a substrate for Renilla luciferases.