(±)-6-bromo-3-(4-bromophenyl)isobenzofuran-1(3H)-one | 38917-90-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (±)-6-bromo-3-(4-bromophenyl)isobenzofuran-1(3H)-one
• 英文别名: 6-Brom-3-(n-bromphenyl)phthalid；6-Bromo-3-[4-bromophenyl]phthalide；6-bromo-3-(4-bromophenyl)-3H-2-benzofuran-1-one
• CAS: 38917-90-7
• 化学式: C₁₄H₈Br₂O₂
• 分子量: 368.024
• InChiKey: FILGVHXBGIUJKR-UHFFFAOYSA-N

物化性质

• 熔点：
  151-152 °C(Solv: ethanol (64-17-5))
• 沸点：
  459.0±45.0 °C(Predicted)
• 密度：
  1.816±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (±)-6-bromo-3-(4-bromophenyl)isobenzofuran-1(3H)-one 在 磷化氢 、 sodium tetrahydroborate 、 硫酸 、 碘 作用下， 以 水 、 丙酸 、 异丙醇 为溶剂， 生成 2,7-二溴蒽
  参考文献：
  名称：

  2,7-二溴萘和2,7-二溴蒽中的卤素-金属互变

  摘要：

  研究了2,7-二溴萘或2,7-二溴蒽与nC 4 H 9 Li之间的卤素金属交换。对于仅交换一个溴原子，在20°C的乙醚中可获得最佳收率，而两个溴原子的交换在-35°C的四氢呋喃中均提供令人满意的收率。

  DOI：

  10.1016/s0022-328x(00)92039-4
• 作为产物：
  描述：

  2-碘苯甲酸甲酯 、 对溴苯甲醛 在 lithium chloro-isopropyl-magnesium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以70%的产率得到(±)-6-bromo-3-(4-bromophenyl)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  A concise synthesis of 3,4-fused spiro[isobenzofuran-3-ones], spiro[furo[3,4- b ]pyridin-5(7 H )-ones], 3-aryl-, and alkylphthalides

  摘要：

  A synthetically useful protocol has been developed for the preparation of highly functionalized 3,4-fused spiro[isobenzofuran-3-ones], spiro[furo[3,4-b]pyridin-5(7H)-ones], 3-aryl-, and alkylphthalides. Reaction of 2-iodobenzoate esters and 2-iodopyridine carboxylate esters with i-PrMgCl center dot LiCl in the presence of cyclic ketones under standard Barbier reaction conditions affords 3,4-fused spiro[isobenzofuran-3-ones] and spiro[furo[3,4-b]pyridin-5(7H)-ones] in good to excellent yields. Step-wise addition of i-PrMgCl center dot LiCl to 2-iodobenzoate esters followed by trapping with various aldehydes yields 3-aryl and 3-alkylphthalides; whereas, under similar conditions access to 3-aryl and 3-alylazaphthalides is also possible. Extension of this methodology toward the preparation of 3-n-butylphthalide and chrycolide, a natural product isolated from the leaves and stems of Chrysanthemum coronarium, is also described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.051

文献信息

• Synthesis of halogenated anthraldehydes and their conversion to antimalarial amino alcohols
  作者：James T. Traxler、E. Patrick Lira、Clarence W. Huffman

  DOI：10.1021/jm00278a025

  日期：1972.8
• PORZI G.; CONCILIO C., J. ORGANOMETAL. CHEM., 1977, 128, NO 1, 95-98
  作者：PORZI G.、 CONCILIO C.

  DOI：——

  日期：——
• A concise synthesis of 3,4-fused spiro[isobenzofuran-3-ones], spiro[furo[3,4- b ]pyridin-5(7 H )-ones], 3-aryl-, and alkylphthalides
  作者：Jeffrey T. Kuethe、Kevin M. Maloney

  DOI：10.1016/j.tet.2013.02.051

  日期：2013.6

  A synthetically useful protocol has been developed for the preparation of highly functionalized 3,4-fused spiro[isobenzofuran-3-ones], spiro[furo[3,4-b]pyridin-5(7H)-ones], 3-aryl-, and alkylphthalides. Reaction of 2-iodobenzoate esters and 2-iodopyridine carboxylate esters with i-PrMgCl center dot LiCl in the presence of cyclic ketones under standard Barbier reaction conditions affords 3,4-fused spiro[isobenzofuran-3-ones] and spiro[furo[3,4-b]pyridin-5(7H)-ones] in good to excellent yields. Step-wise addition of i-PrMgCl center dot LiCl to 2-iodobenzoate esters followed by trapping with various aldehydes yields 3-aryl and 3-alkylphthalides; whereas, under similar conditions access to 3-aryl and 3-alylazaphthalides is also possible. Extension of this methodology toward the preparation of 3-n-butylphthalide and chrycolide, a natural product isolated from the leaves and stems of Chrysanthemum coronarium, is also described. (C) 2013 Elsevier Ltd. All rights reserved.
• Halogen—metal interconversion in 2,7-dibromonaphthalene and 2,7-dibromoanthracene
  作者：Gianni Porzi、Carlo Concilio

  DOI：10.1016/s0022-328x(00)92039-4

  日期：1977.3

  The halogen—metal exchange between 2,7-dibromonaphthalene or 2,7-dibromoanthracene and n-C4H9Li has been investigated. For exchange of only one bromine atom the best yields are achieved in diethyl ether at 20° C, while the exchange of both bromine atoms gives satisfactory yields in tetrahydrofuran at −35° C.

  研究了2,7-二溴萘或2,7-二溴蒽与nC 4 H 9 Li之间的卤素金属交换。对于仅交换一个溴原子，在20°C的乙醚中可获得最佳收率，而两个溴原子的交换在-35°C的四氢呋喃中均提供令人满意的收率。