methyl 3-[(2Z)-5-[(3R,4R)-4-carbamoyl-3-methylhex-1-ynyl]-2-[[5-[(3R,4R)-4-carbamoyl-3-methylhex-1-ynyl]-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methylidene]-4-methylpyrrol-3-yl]propanoate | 164172-17-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 3-[(2Z)-5-[(3R,4R)-4-carbamoyl-3-methylhex-1-ynyl]-2-[[5-[(3R,4R)-4-carbamoyl-3-methylhex-1-ynyl]-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methylidene]-4-methylpyrrol-3-yl]propanoate
• CAS: 164172-17-2
• 化学式: C₃₅H₄₆N₄O₆
• 分子量: 618.773
• InChiKey: AINNIEUHHDYBPJ-NUJDCYSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  167
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-[(2Z)-5-[(3R,4R)-4-carbamoyl-3-methylhex-1-ynyl]-2-[[5-[(3R,4R)-4-carbamoyl-3-methylhex-1-ynyl]-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methylidene]-4-methylpyrrol-3-yl]propanoate 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以89%的产率得到methyl 3-[(2Z)-2-[[5-[(3R,4R)-4-carbamoyl-3-methylhex-1-ynyl]-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methylidene]-5-[(Z)-[(3R,4R)-4-ethyl-3-methyl-5-oxopyrrolidin-2-ylidene]methyl]-4-methylpyrrol-3-yl]propanoate
  参考文献：
  名称：

  New Strategies for the Synthesis of Biologically Important Tetrapyrroles. The “B,C + D + A” Approach to Linear Tetrapyrroles

  摘要：

  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).

  DOI：

  10.1021/jo991503u
• 作为产物：
  描述：

  5-(苄氧羰基)-2,4-二甲基-3-吡咯丙酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium on activated charcoal 氢气 、 溴 、 碘 、 碳酸氢钠 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 14.17h， 生成 methyl 3-[(2Z)-5-[(3R,4R)-4-carbamoyl-3-methylhex-1-ynyl]-2-[[5-[(3R,4R)-4-carbamoyl-3-methylhex-1-ynyl]-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methylidene]-4-methylpyrrol-3-yl]propanoate
  参考文献：
  名称：

  New Strategies for the Synthesis of Biologically Important Tetrapyrroles. The “B,C + D + A” Approach to Linear Tetrapyrroles

  摘要：

  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).

  DOI：

  10.1021/jo991503u

文献信息

• 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.
• 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).