5-acetoxymetyl-4-acetyl-2-benzyloxycarbonyl-3-methyl-1H-pyrrole | 19996-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-acetoxymetyl-4-acetyl-2-benzyloxycarbonyl-3-methyl-1H-pyrrole
• 英文别名: benzyl 5-acetoxymethyl-4-acetyl-3-methylpyrrole-2-carboxylate；5-acetoxymethyl-4-acetyl-3-methyl-pyrrole-2-carboxylic acid benzyl ester；2-Acetoxymethyl-4-methyl-3-acetyl-5-benzyloxycarbonyl-pyrrol；benzyl 4-acetyl-5-(acetyloxymethyl)-3-methyl-1H-pyrrole-2-carboxylate
• CAS: 19996-71-5
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: IZOZYPGIBDWMAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  85.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-acetoxymetyl-4-acetyl-2-benzyloxycarbonyl-3-methyl-1H-pyrrole 在 四氟硼酸-二乙醚络合物 、 sodium tetrahydroborate 、 三氟甲磺酸 、 palladium on activated charcoal 、 氢气 、 碘 、 乙酸酐 、 碳酸氢钠 、 苯甲酰氯 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~100.0 ℃ 、100.0 kPa 条件下， 生成 Disodium salt protoporphyrin IX
  参考文献：
  名称：

  Total Synthesis of Hematoporphyrin and Protoporphyrin; a Conceptually New Approach

  摘要：

  原文翻译如下： 报道了使用一种新的替代方法合成原卟啉IX及其二钠盐的总合成，该方法取代了传统的MacDonald缩合反应。关键步骤是将新的非对称二碘二吡咯甲烷1与已知的二吡咯甲烷2反应。这两个片段的偶联直接导致卟啉3的形成，无需氧化剂。这种新方法非常适合在多100克的规模上合成高质量的原卟啉IX衍生物，而无需进行色谱分离。此外，这些制备完全不含任何动物来源的污染物，这在原卟啉IX衍生物的制造中代表了一个真正的改进。

  DOI：

  10.2533/chimia.2013.204
• 作为产物：
  描述：

  benzyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate 在 磺酰氯 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 5-acetoxymetyl-4-acetyl-2-benzyloxycarbonyl-3-methyl-1H-pyrrole
  参考文献：
  名称：

  Chunchatprasert, Laddawan; Rao, K. R. Nagaraja; Shannon, Patrick V. R., Journal of the Chemical Society. Perkin transactions I, 1992, # 14, p. 1779 - 1784

  摘要：

  DOI：

文献信息

• Total Synthesis of Hematoporphyrin and Protoporphyrin: A Conceptually New Approach
  作者：Pierre Martin、Markus Mueller、Dietmar Flubacher、Andreas Boudier、Hans-Ulrich Blaser、Dirk Spielvogel

  DOI：10.1021/op100036c

  日期：2010.7.16

  The total synthesis of protoporphyrin IX and its disodium salt using a new alternative method to the classical MacDonald condensation is reported. The key step is the reaction of the new unsymmetrical diiodo dipyrrylmethane 1 with the known dipyrrylmethane 2. Coupling of the two fragments leads directly to porphyrin 3 without the need of an oxidizing agent. The new methodology is well suited for the

  据报道，使用一种经典的麦克唐纳缩合的新方法，原卟啉phy及其二钠盐的全合成。关键步骤是新的不对称二碘二吡咯基甲烷1与已知的二吡咯基甲烷2的反应。两个片段的偶联直接导致卟啉3，而无需氧化剂。该新方法非常适合以高质量进行多100 g规模的原卟啉IX衍生物的合成，而无需进行色谱分离。此外，这些制剂完全不含任何动物来源的污染物，这代表了原卟啉IX衍生物生产中的真正改进。
• Process For Preparing Porphyrin Derivatives, Such As Protoporphyrin (IX) And Synthesis Intermediates
  申请人：Martin Pierre

  公开号：US20080242857A1

  公开（公告）日：2008-10-02

  The present invention relates to a process for preparing a porphyrin of formula (I), optionally in the form of a salt with an alkali metal and/or in the form of a metal complex: in which: R and R′ are as defined in claim 1 , comprising: a step of condensation, in an acidic medium, between a dipyrromethane of formula (II): in which R′b is as defined above for (I), and a dipyrromethane of formula (III): in which R″ is as defined in claim 1 , and also the compounds of formula (III).

  本发明涉及一种制备公式（I）的卟啉的方法，可选地以碱金属的盐形式和/或金属配合物的形式存在： 其中： R和R′如权利要求1中定义的那样， 包括： 在酸性介质中，通过公式（II）的二吡咯甲烷和公式（III）的二吡咯甲烷之间的缩合步骤： 其中R′b如上述（I）中定义的那样， 以及公式（III）的化合物。
• Tricyclic derivatives and their use as anti-cancer agents
  申请人：Univ. College Cardiff Consultants

  公开号：US06201129B1

  公开（公告）日：2001-03-13

  A compound having the formula wherein R1 is COOR8 wherein R8 is alkyl having from 1 to 10 carbon atoms or aralkyl, the aralkyl having from one to four carbon atoms in the alkyl portion and a carbocyclic or heterocyclic group in the aryl portion; R2 is H, alkyl having from 1 to 10 carbon atoms, or COOR7 wherein R7 is alkyl having from 1 to 10 carbon atoms; R3 is H, alkyl having from 1 to 10 carbon atoms, or COOR8; R4 is H, alkyl having from 1 to 10 carbon atoms, or COOR8; R5 is H, alkyl having from 1 to 10 carbon atoms, aralkyl having from 1 to 4 carbon atoms in the alkyl portion, aryl having from 1 to 10 carbon atoms, acyl having from 1 to 10 carbon atoms, or COOCH3; and R6 is H or COOCH3; and thereof.

  一种化合物，其化学式为：其中，R1为COOR8，其中R8为1至10个碳原子的烷基或苄基，苄基在烷基部分有1至4个碳原子，并且在芳基部分有一个碳环或杂环基团；R2为H，1至10个碳原子的烷基，或COOR7，其中R7为1至10个碳原子的烷基；R3为H，1至10个碳原子的烷基，或COOR8；R4为H，1至10个碳原子的烷基，或COOR8；R5为H，1至10个碳原子的烷基，1至4个碳原子的苄基，1至10个碳原子的芳基，1至10个碳原子的酰基，或COOCH3；R6为H或COOCH3；以及该化合物。
• Anti-tumour heterocycles. Part xiv. A new route to pyrrolo-[3,2-f]indoles and the novel pyrrolo[3,2-f; 4,5-f′]diindole system
  作者：Laddawan Chunchatprasert、Patrick V. R. Shannon

  DOI：10.1039/p19960001787

  日期：——

  Vilsmeier formylation of the dipyrrolylmethane 14a gave the 8-formylpyrrolo[3,2-f]indole 15. Alternatively, condensation of the pyrrole 1a with a variety of 2,3-unsubstituted pyrroles 16a-e in the presence of Montmorillonite K-10 clay gave, in general, the corresponding pyrrolo[3,2-f]indoles 19 and 21a-d. These pyrroloindoles were unambiguously structurally indentified by H-1 NMR spectra and NOE experiments, Amongst the by-products of the reaction were the corresponding pyrrolo [2,3-f]indoles, uncyclised 2-monosubstituted intermediate pyrroles and the 2,3-disubstituted derivatives. Similar results were obtained by replacing the ethyl ester la by the benzyl ester 1b.The pyrrole 1a, with K-10 clay and the tetrahydroindole 24 gave only a very low yield of the spirocyclopentylpyrrolo [1,2-f]indole 25, but with the N-benzyl-4-oxotetrahydroindole 27b gave both the tetrahydropyrrolo[2,3-b]carbazole 28 and its [3,2-b] isomer 29 and other products.]The pyrrole 1a condensed with N-methoxycarbonylpyrrole 32 to give the pyrrolo[3,2-f]indole 33, its isomer 34, the monosubstituted intermediate 35 and the two products 36 and 37 resulting from disubstitution. Both of these (36 and 37) were cyclised with toluene-p-sulfonic acid to the novel pentacyclic pyrrolo[3,2-f;4,5-f']diindole 38.Regiospecific hydrolysis and decarboxylation of the N-methoxycarbonylpyrroloindole 33 gave the 2,3-unsubstituted pyrrolo [3,2-f]indole 21k, which on Vilsmeier formylation gave the 8-formyl derivative 39b.
• Chunchatprasert, Laddawan; Shannon, Patrick V. R., Journal of the Chemical Society. Perkin transactions I, 1994, # 13, p. 1765 - 1772
  作者：Chunchatprasert, Laddawan、Shannon, Patrick V. R.

  DOI：——

  日期：——