5-[(3R,4R)-3-((S)-1-Benzyloxy-ethyl)-4-carbamoyl-pent-1-ynyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester | 145100-18-1

• 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-[(3R,4R)-3-((S)-1-Benzyloxy-ethyl)-4-carbamoyl-pent-1-ynyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 5-[(3R,4R)-5-amino-4-methyl-5-oxo-3-[(1S)-1-phenylmethoxyethyl]pent-1-ynyl]-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrole-2-carboxylate
• CAS: 145100-18-1
• 化学式: C₂₉H₃₈N₂O₆
• 分子量: 510.631
• InChiKey: YHUZOARJUDXEKZ-URVUXULASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[(3R,4R)-3-((S)-1-Benzyloxy-ethyl)-4-carbamoyl-pent-1-ynyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester 在 四丁基氟化铵 作用下， 以86%的产率得到5-[(3R,4R)-3-((S)-1-Benzyloxy-ethyl)-4-methyl-5-oxo-pyrrolidin-(2Z)-ylidenemethyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  明确合成植物色素的环A，B二氢吡咯烷酮

  摘要：

  Dihydropyrromethenone 1b（R =对甲氧基苄基），潜在的前体，用于合成植物色素（3），已从对映体纯的形式制备，从同型手性炔内酯18开始。

  DOI：

  10.1016/0040-4039(95)00032-8
• 作为产物：
  描述：

  氰乙酸叔丁酯 在 copper(l) iodide 、 四(三苯基膦)钯 N-碘代丁二酰亚胺 、 t-butyltetramethyl-guanidine 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 生成 5-[(3R,4R)-3-((S)-1-Benzyloxy-ethyl)-4-carbamoyl-pent-1-ynyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Tetrapyrroles. IV. A highly efficient synthesis of homochiral dihydropyrromethenones via Pdo mediated coupling of iodopyrroles and acetylenic amides

  摘要：

  Homochiral dihydropyrromethenones of type 20 have been synthesized in a highly efficient manner by Pd(o) mediated coupling of iodopyrrole 14 with acetylenic amides 18, followed by F- catalyzed 5-exo-dig cyclization. In analogous fashion, phytochrome (8) precursor 25a has been prepared in 85% overall yield from iodopyrrole 22.

  DOI：

  10.1016/s0040-4039(00)60941-3

文献信息

• An unequivocal synthesis of the ring-A,B dihydropyrromethenone of phytochrome
  作者：Peter A. Jacobi、Jiasheng Guo、Wanjun Zheng

  DOI：10.1016/0040-4039(95)00032-8

  日期：1995.2

  Dihydropyrromethenone 1b (R = p-methoxybenzyl), a potential precursor for the synthesis of phytochrome (3), has been prepared in enantiomerically pure form beginning with the homochiral acetylenic lactone 18.

  Dihydropyrromethenone 1b（R =对甲氧基苄基），潜在的前体，用于合成植物色素（3），已从对映体纯的形式制备，从同型手性炔内酯18开始。
• Dihydropyrromethenones by Pd(0)-Mediated Coupling of Iodopyrroles and Acetylenic Amides. Synthesis of the A,B-Ring Segment of Phytochrome
  作者：Peter A. Jacobi、Jiasheng Guo、S. Rajeswari、Wanjun Zheng

  DOI：10.1021/jo970289b

  日期：1997.5.1

  Dihydropyrromethenone derivative 32b, which constitutes the A,B-ring segment of phytochrome (6), has been prepared in enantiomerically pure form beginning with acetylenic amide 47b and iodopyrrole 27. The key steps involved the TBAF-catalyzed 5-exo-dig cyclization of the acetylenic pyrrole 48b, followed by thia-Mitsunobu inversion of the resulting alcohol derivative 31b.
• Tetrapyrroles. IV. A highly efficient synthesis of homochiral dihydropyrromethenones via Pdo mediated coupling of iodopyrroles and acetylenic amides
  作者：Peter A. Jacobi、S. Rajeswari

  DOI：10.1016/s0040-4039(00)60941-3

  日期：1992.10

  Homochiral dihydropyrromethenones of type 20 have been synthesized in a highly efficient manner by Pd(o) mediated coupling of iodopyrrole 14 with acetylenic amides 18, followed by F- catalyzed 5-exo-dig cyclization. In analogous fashion, phytochrome (8) precursor 25a has been prepared in 85% overall yield from iodopyrrole 22.