benzyl 3-(2-methoxycarbonylethyl)-4,5-dimethylpyrrole-2-carboxylate | 33317-06-5

• 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: benzyl 3-(2-methoxycarbonylethyl)-4,5-dimethylpyrrole-2-carboxylate
• 英文别名: benzyl 3-(3-methoxy-3-oxopropyl)-4,5-dimethyl-1H-pyrrole-2-carboxylate
• CAS: 33317-06-5
• 化学式: C₁₈H₂₁NO₄
• 分子量: 315.369
• InChiKey: YEUNLBHBVPJFGD-UHFFFAOYSA-N

物化性质

• 熔点：
  95 °C(Solv: methanol (67-56-1))
• 沸点：
  485.8±45.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 3-(2-methoxycarbonylethyl)-4,5-dimethylpyrrole-2-carboxylate 在 氢溴酸 、 溶剂黄146 、 copper dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.57h， 生成 2,7-di(2-methoxycarbonylethyl)-3,8,12,17-tetramethyl-13,18-divinylporphyrin
  参考文献：
  名称：

  Smith, Kevin M.; Pandey, Ravindra K., Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 1041 - 1044

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-ethoxycarbonyl-4-benzyloxycarbonyl-5-methylpyrrole-3-propionate 在 乙醇 、 sodium 、 镍 作用下， 100.0~150.0 ℃ 、9.81 MPa 条件下， 生成 benzyl 3-(2-methoxycarbonylethyl)-4,5-dimethylpyrrole-2-carboxylate
  参考文献：
  名称：

  Hayes et al., Journal of the Chemical Society, 1958, p. 3779,3782

  摘要：

  DOI：

文献信息

• Bile pigment studies-VII New syntheses of biliverdin-IXα dimethyl ester and two related mono-vinyl-mono-ethyl isomers
  作者：Kevin M. Smith、Ravindra K. Pandey

  DOI：10.1016/s0040-4020(01)91126-3

  日期：1984.1

  Using the recently developed route through di-t-butyl b-bilene-1,19-dicarboxylates, new syntheses of biliverdin-IXα dimethyl ester (1) and two related mono-vinyl-mono-ethyl isomers (2) and (3), are described. The two dihydro-derivatives of (1) are important in connection with biosynthetic studies of the origin of algal biliproteins.

  使用最近开发的通过b-bilene-1,19-二羧酸二叔丁酯的路线，合成了biliverdin-IXα二甲基酯（1）和两个相关的单乙烯基-单乙基异构体（2）和（3）进行说明。（1）的两种二氢衍生物在藻类胆蛋白起源的生物合成研究中很重要。
• Synthetic and biosynthetic studies of porphyrins. Part 8. Syntheses of hepta-, hexa-, and penta-carboxylic porphyrins related to uroporphyrin-I
  作者：Anthony H. Jackson、Damrus Supphayen

  DOI：10.1039/p19870000277

  日期：——

  The title porphyrins, of interest as abnormal metabolites in porphyrin biosynthesis, have been synthesized by the Fischer, and b-oxobilane routes, and compared with the naturally derived materials. Enzymic experiments have shown that the conversion of uroporphyrinogen-I into coproporphyrinogen-I both in vivo and in vitro is non-specific and occurs by both possible pathways via the two intermediate

  标题卟啉，作为卟啉生物合成中的异常代谢产物，已经通过费歇尔和b-氧杂环丁烷路线合成，并与天然物质进行了比较。酶学实验表明，尿卟啉原-I在体内和体外的转化都是非特异性的，并且通过两种中间的六羧酸卟啉原通过两种可能的途径发生。
• Investigations regarding the utility of prodigiosenes to treat leukemia
  作者：Deborah A. Smithen、A. Michael Forrester、Dale P. Corkery、Graham Dellaire、Julie Colpitts、Sherri A. McFarland、Jason N. Berman、Alison Thompson

  DOI：10.1039/c2ob26535d

  日期：——

  Prodigiosenes, possessing a 4-methoxypyrrolyldipyrrin skeleton, are known for their anti-cancer activity. Structural modification of the C-ring resulted in a series of prodigiosenes that displayed promising activity against leukemia cell lines during in vitro analysis against the NCI 60 cancer cell line panel. Further in vivo studies of these compounds using the zebrafish model showed persistence of anti-leukemia properties in human K562 chronic myelogenous leukemia cells.

  灵菌烯具有 4-甲氧基吡咯基二吡林骨架，以其抗癌活性而闻名。 C 环的结构修饰产生了一系列灵菌烯，在针对 NCI 60 癌细胞系组的体外分析中，这些灵菌烯显示出针对白血病细胞系的有希望的活性。使用斑马鱼模型对这些化合物进行的进一步体内研究表明，在人类 K562 慢性粒细胞白血病细胞中具有持久的抗白血病特性。
• Normal and Abnormal Heme Biosynthesis. 2.¹ Synthesis and Metabolism of Type-III Pentacarboxylic Porphyrinogens:  Further Experimental Evidence for the Enzymic Clockwise Decarboxylation of Uroporphyrinogen-III
  作者：Timothy D. Lash、Ukti N. Mani、Elizabeth A. Lyons、Pornlert Thientanavanich、Marjorie A. Jones

  DOI：10.1021/jo9814748

  日期：1999.1.1

  Uroporphyrinogen decarboxylase catalyses the sequential decarboxylation of uroporphyrinogen-III (1) to-give coproporphyrinogen-III (2), a precursor to the hemes and chlorophylls. This involves the decarboxylation of four nonequivalent acetate side chains to produce methyl units and in principle could take place by 24 different pathways involving up to 14 intermediary porphyrinogens. In the past, seemingly contradictory data have been presented that either support an ordered "clockwise" decarboxylation pathway or a random decarboxylation process. Four pentacarboxylate porphyrinogens might be involved immediately before the formation of 2, and these compounds have been synthesized as the corresponding porphyrin pentamethyl esters via tripyrrene and a,c-biladiene intermediates. Hydrolysis of the methyl esters and reduction with 3% sodium amalgam gave the required porphyrinogens, and these were incubated with crude enzyme preparations derived from chicken red cell hemolysates. One of these pentacarboxylate porphyrinogens (5dab) consistently proved to be a much better substrate than the other three, providing new support for the "clockwise" pathway for coproporphyrinogen-III formation.
• Aucken, Christopher J.; Leeper, Finian J.; Battersby, Alan R., Journal of the Chemical Society. Perkin transactions I, 1997, # 14, p. 2099 - 2109
  作者：Aucken, Christopher J.、Leeper, Finian J.、Battersby, Alan R.

  DOI：——

  日期：——