1,2-bis(allyloxy)-4,5-dibromobenzene | 914300-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2-bis(allyloxy)-4,5-dibromobenzene
• 英文别名: 1,2-Dibromo-4,5-bis(prop-2-enoxy)benzene
• CAS: 914300-25-7
• 化学式: C₁₂H₁₂Br₂O₂
• 分子量: 348.034
• InChiKey: HKQMDTMKGSLRSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-bis(allyloxy)-4,5-dibromobenzene 在 吗啉 、 四(三苯基膦)钯 、 正丁基锂 、 dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II) 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 12.0h， 生成 3,4-dihydroxy-7,8-dimethoxy-6H-naphtho[1,2-b]benzo[d]pyran-6-one
  参考文献：
  名称：

  Nickel-Catalyzed Synthesis of Benzocoumarins:  Application to the Total Synthesis of Arnottin I

  摘要：

  The ring-opening addition of methyl 2,3-dimethoxy-6-iodobenzoate to oxabenzonorbornadienes followed by cyclization in the presence of NiBr2( dppe) and Zn metal powder in acetonitrile at 80 C to give the corresponding benzocoumarin derivatives is described. This methodology was then applied to the synthesis of natural product arnottin I, first isolated from Xanthoxylum arnottianum Maxim, using protecting group chemistry. After deprotection and subsequent ring closure, arnottin I was obtained in 21% overall yield after six steps starting from catechol.

  DOI：

  10.1021/jo061477h
• 作为产物：
  描述：

  邻苯二酚 在 溴 、 sodium carbonate 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 44.0h， 生成 1,2-bis(allyloxy)-4,5-dibromobenzene
  参考文献：
  名称：

  Peripheral and Axial Substitution of Phthalocyanines with Solketal Groups:  Synthesis and In Vitro Evaluation for Photodynamic Therapy

  摘要：

  Phthalocyanines (Pcs) are a class of photosensitizers (PSs) with a strong tendency to aggregate in aqueous environment, which has a negative influence on their photosensitizing ability in photodynamic therapy. Pcs with either peripheral or axial solketal substituents, that is, ZnPc(sol)(8) and Si(sol)(2)Pc, respectively, were synthesized and their tendency to aggregate as well as their photodynamic properties in 14C and B16F10 cell lines were evaluated. The results were compared to more hydrophilic silicon Pcs, that is, Si(PEG750)(2)Pc and Pc4. The order of cellular uptake was Pc4 > ZnPc(sol)(8) > Si(PEG750)(2)Pc > Si(sol(2))Pc. In contrast, Si(sol(2))Pc showed the highest photocytotoxicity, while ZnPc(sol)(8) did not show any photocytotoxicity up to a concentration of 10 mu M in both cell types. UV/vis spectroscopy showed that Si(sol)(2)Pc is less prone to aggregation than ZnPc(sol)(8), which can explain the lack of photoactivity of the latter. Si(sol)(2)Pc was predominantly located in lipid droplets, whereas Si(PEG750)(2)Pc was homogeneously distributed in the cytosol, which is probably the main cause of their difference in photoactivity. The very high photodynamic efficacy of Si(sol)(2)Pc makes this PS an interesting candidate for future studies.

  DOI：

  10.1021/jm061136w

文献信息

• HOLLMANN, K.;ECKE, M.;MUNLSTADT, M., CHEMIEDOZENTENTAG., 1988, LEIPZIG, 23-25 MARZ, 1988, BERLIN,(S. A.) C. 41
  作者：HOLLMANN, K.、ECKE, M.、MUNLSTADT, M.

  DOI：——

  日期：——
• Peripheral and Axial Substitution of Phthalocyanines with Solketal Groups:  Synthesis and In Vitro Evaluation for Photodynamic Therapy
  作者：Jan-Willem Hofman、Femke van Zeeland、Selcan Turker、Herre Talsma、Saskia A. G. Lambrechts、Dmitri V. Sakharov、Wim E. Hennink、Cornelus F. van Nostrum

  DOI：10.1021/jm061136w

  日期：2007.4.1

  Phthalocyanines (Pcs) are a class of photosensitizers (PSs) with a strong tendency to aggregate in aqueous environment, which has a negative influence on their photosensitizing ability in photodynamic therapy. Pcs with either peripheral or axial solketal substituents, that is, ZnPc(sol)(8) and Si(sol)(2)Pc, respectively, were synthesized and their tendency to aggregate as well as their photodynamic properties in 14C and B16F10 cell lines were evaluated. The results were compared to more hydrophilic silicon Pcs, that is, Si(PEG750)(2)Pc and Pc4. The order of cellular uptake was Pc4 > ZnPc(sol)(8) > Si(PEG750)(2)Pc > Si(sol(2))Pc. In contrast, Si(sol(2))Pc showed the highest photocytotoxicity, while ZnPc(sol)(8) did not show any photocytotoxicity up to a concentration of 10 mu M in both cell types. UV/vis spectroscopy showed that Si(sol)(2)Pc is less prone to aggregation than ZnPc(sol)(8), which can explain the lack of photoactivity of the latter. Si(sol)(2)Pc was predominantly located in lipid droplets, whereas Si(PEG750)(2)Pc was homogeneously distributed in the cytosol, which is probably the main cause of their difference in photoactivity. The very high photodynamic efficacy of Si(sol)(2)Pc makes this PS an interesting candidate for future studies.
• Nickel-Catalyzed Synthesis of Benzocoumarins:  Application to the Total Synthesis of Arnottin I
  作者：Sachin Madan、Chien-Hong Cheng

  DOI：10.1021/jo061477h

  日期：2006.10.1

  The ring-opening addition of methyl 2,3-dimethoxy-6-iodobenzoate to oxabenzonorbornadienes followed by cyclization in the presence of NiBr2( dppe) and Zn metal powder in acetonitrile at 80 C to give the corresponding benzocoumarin derivatives is described. This methodology was then applied to the synthesis of natural product arnottin I, first isolated from Xanthoxylum arnottianum Maxim, using protecting group chemistry. After deprotection and subsequent ring closure, arnottin I was obtained in 21% overall yield after six steps starting from catechol.