3-{5-[5-Imino-3-methyl-4-vinyl-5H-furan-(2Z)-ylidenemethyl]-2-[1-[5-iodo-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-4-methyl-2H-pyrrol-3-yl}-propionic acid methyl ester | 256638-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 3-{5-[5-Imino-3-methyl-4-vinyl-5H-furan-(2Z)-ylidenemethyl]-2-[1-[5-iodo-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-4-methyl-2H-pyrrol-3-yl}-propionic acid methyl ester
• CAS: 256638-26-3
• 化学式: C₂₇H₃₀IN₃O₅
• 分子量: 603.457
• InChiKey: PBXHEKHXOUTTPM-FCPDBWOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  113.83
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2(R)-methyl-3(R)-<1'(S)-hydroxyethyl>-4-pentynoic acid amide 、 3-{5-[5-Imino-3-methyl-4-vinyl-5H-furan-(2Z)-ylidenemethyl]-2-[1-[5-iodo-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-4-methyl-2H-pyrrol-3-yl}-propionic acid methyl ester 在 tris-(dibenzylideneacetone)dipalladium(0) 三(2-呋喃基)膦 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以63%的产率得到methyl 3-[(2Z)-5-[(Z)-(4-ethenyl-3-methyl-5-oxofuran-2-ylidene)methyl]-2-[[5-[(Z)-[(3S,4R)-3-[(1S)-1-hydroxyethyl]-5-imino-4-methyloxolan-2-ylidene]methyl]-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
• 作为产物：
  描述：

  3-{5-((Z)-4-Carbamoyl-3-methyl-hexa-3,5-dien-1-ynyl)-2-[1-[5-iodo-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-4-methyl-2H-pyrrol-3-yl}-propionic acid methyl ester 以 氯仿 为溶剂， 反应 31.0h， 以32%的产率得到3-{5-[5-Imino-3-methyl-4-vinyl-5H-furan-(2Z)-ylidenemethyl]-2-[1-[5-iodo-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-4-methyl-2H-pyrrol-3-yl}-propionic acid methyl ester
  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