methyl 3-[5-iodo-2-[[5-iodo-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methyl]-4-methyl-1H-pyrrol-3-yl]propanoate | 130468-97-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-[5-iodo-2-[[5-iodo-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methyl]-4-methyl-1H-pyrrol-3-yl]propanoate
• CAS: 130468-97-2
• 化学式: C₁₉H₂₄I₂N₂O₄
• 分子量: 598.22
• InChiKey: HBPNEPUYGWZEOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-[5-iodo-2-[[5-iodo-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methyl]-4-methyl-1H-pyrrol-3-yl]propanoate 在 四(三苯基膦)钯 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 、 二氯甲烷 为溶剂， 反应 24.17h， 生成 3-{5-[(Z)-4-Carbamoyl-6-(4-chloro-phenylselanyl)-3-methyl-hex-3-en-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
  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：

  dibenzyl 3,3'-bis(2-methoxycarbonylethyl)-4,4'-dimethyl-2,2'-pyrromethane-5,5'-dicarboxylate 在 palladium on activated charcoal 氢气 、 碘 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 生成 methyl 3-[5-iodo-2-[[5-iodo-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methyl]-4-methyl-1H-pyrrol-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

• Long wavelength red fluorescent dyes from 3,5-diiodo-BODIPYs
  作者：Lijuan Jiao、Changjiang Yu、Timsy Uppal、Mingming Liu、Yan Li、Yunyou Zhou、Erhong Hao、Xiaoke Hu、M. Graça H. Vicente

  DOI：10.1039/c001068e

  日期：——

  Amphiphilic and long wavelength red fluorescent dyes (4 and 7) were prepared from the Sonogashira coupling reactions of 3,5-diiodo-BODIPYs (1 and 6). One of these compounds, BODIPY 7, readily accumulated within human carcinoma HEp2 cells and was found to localize mainly within the endoplasmic reticulum (ER).

  通过 3,5-二碘-BODIPY（1 和 6）的 Sonogashira 偶联反应制备两亲性长波长红色荧光染料（4 和 7）。其中一种化合物 BODIPY 7 很容易在人癌 HEp2 细胞内积累，并被发现主要定位于内质网 (ER) 内。
• 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.
• Beckmann, Stefan; Wessel, Thomas; Franck, Burchard, Angewandte Chemie, 1990, vol. 102, # 12, p. 1439 - 1441
  作者：Beckmann, Stefan、Wessel, Thomas、Franck, Burchard、Hoenle, Wolfgang、Borrmann, Horst、Schnering, Hans Georg von

  DOI：——

  日期：——
• BECKMANN, STEFAN;WESSEL, THOMAS;FRANCK, BURCHARD;HONLE, WOLFGANG;BORRMANN+, ANGEW. CHEM., 102,(1990) N2, C. 1439-1441
  作者：BECKMANN, STEFAN、WESSEL, THOMAS、FRANCK, BURCHARD、HONLE, WOLFGANG、BORRMANN+

  DOI：——

  日期：——