5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidin-(2Z)-ylidenemethyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester | 188923-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidin-(2Z)-ylidenemethyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 5-[(Z)-[(3R,4R)-3-[(1S)-1-hydroxyethyl]-1-[(4-methoxyphenyl)methyl]-4-methyl-5-oxopyrrolidin-2-ylidene]methyl]-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrole-2-carboxylate
• CAS: 188923-17-3
• 化学式: C₃₀H₄₀N₂O₇
• 分子量: 540.657
• InChiKey: CUIISKJSDIOPFP-KQEGWZHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidin-(2Z)-ylidenemethyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester 生成 5-[(3R,4R)-3-((R)-1-Acetylsulfanyl-ethyl)-1-(4-methoxy-cyclohexa-1,5-dienylmethyl)-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：

  (2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoic acid 在 copper(l) iodide 、 四(三苯基膦)钯 、 tetraphosphorus decasulfide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 227.0h， 生成 5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-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：

  Dihydropyrromethenones by Pd(0)-Mediated Coupling of Iodopyrroles and Acetylenic Amides. Synthesis of the A,B-Ring Segment of Phytochrome

  摘要：

  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.

  DOI：

  10.1021/jo970289b

文献信息

• 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.
• 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。