2(R)-methyl-3(R)-<1'(S)-hydroxyethyl>-4-pentynoic acid amide | 162612-31-9

• 分子结构分类: 有机化合物
• 英文名称: 2(R)-methyl-3(R)-<1'(S)-hydroxyethyl>-4-pentynoic acid amide
• 英文别名: (2R,3R)-3-[(1S)-1-hydroxyethyl]-2-methylpent-4-ynamide
• CAS: 162612-31-9
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: DWGLLSOLYVVIJL-VQVTYTSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2(R)-methyl-3(R)-<1'(S)-hydroxyethyl>-4-pentynoic acid amide 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.0h， 生成 5-[(3R,4R)-3-((S)-1-Hydroxy-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：

  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
• 作为产物：
  描述：

  (2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoic acid 在 tetraphosphorus decasulfide 、 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 64.0h， 生成 2(R)-methyl-3(R)-<1'(S)-hydroxyethyl>-4-pentynoic acid amide
  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

• 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。
• New Strategies for the Synthesis of Biologically Important Tetrapyrroles. The “B,C + D + A” Approach to Linear Tetrapyrroles
  作者：Peter A. Jacobi、Lisa D. Coutts、Jiasheng Guo、Sheila I. Hauck、Sam H. Leung

  DOI：10.1021/jo991503u

  日期：2000.1.1

  Linear tetrapyrroles related to phytochrome (1) were prepared in enantiospecific fashion by a new strategy beginning with ring-B,C synthons of type 19 (bis-iododipyrrins). Rings A and D were elaborated by Pd(0)-mediated coupling of 19a with the appropriate alkyne acid or amide derivatives 9 and 20, followed by intramolecular cyclization (method C: BC + D + A --> ABCD).
• A conceptually new approach to the synthesis of linear tetrapyrroles related to phytochrome
  作者：Peter A. Jacobi、Jiasheng Guo

  DOI：10.1016/0040-4039(95)00376-n

  日期：1995.4

  Linear tetrapyrroles 9, of a type related to phytochrome (3), have been prepared by TBAF catalyzed 5-exo-dig cyclization of bis-acetylenic amides 8.