6'-(Diethylamino)-N,N-diethyl-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthen]-3'(9'aH)-iminium | 866464-50-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6'-(Diethylamino)-N,N-diethyl-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthen]-3'(9'aH)-iminium
• 英文别名: [6'-(diethylamino)-3-oxospiro[2-benzofuran-1,9'-9aH-xanthene]-3'-ylidene]-diethylazanium
• CAS: 866464-50-8
• 化学式: C₂₈H₃₁N₂O₃
• 分子量: 443.566
• InChiKey: NNAQLBSKLBFVAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  41.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6'-(Diethylamino)-N,N-diethyl-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthen]-3'(9'aH)-iminium 在 盐酸 作用下， 以 水 为溶剂， 生成 C.I.颜料紫1
  参考文献：
  名称：

  Synthesis, chemical reactivity, and photophysical properties of 2′,7′ phenylated rhodamine dyes

  摘要：

  While exploring water soluble rhodamine based fluorescent polymeric systems for biological imaging applications we came across new rhodamine derivatives that possess interesting optical properties. We report the synthesis of three different 2 ',7 '-diphenylated rhodamine derivatives (1-3) with distinct photophysical properties. The three rhodamine derivatives differ by the number of methyl groups present on the nitrogens and their absorption maxima are red-shifted on increased methylation. We observed an unusual inertness of these compounds toward traditional DCC-DMAP esterification conditions, which we attribute to the ease of lactonization in the presence of even minute amounts of the nucleophile/base DMAP (pK(a) = 9.2). Synthesis of acrylate esters was successfully accomplished using MSNT (1-(Mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole) coupling conditions using a much milder nucleophile/base, for example, N-methyl imidazole (pK(a) = 6.95). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.124
• 作为产物：
  描述：

  C.I.颜料紫1 在 sodium hydroxide 作用下， 生成 6'-(Diethylamino)-N,N-diethyl-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthen]-3'(9'aH)-iminium
  参考文献：
  名称：

  Synthesis, chemical reactivity, and photophysical properties of 2′,7′ phenylated rhodamine dyes

  摘要：

  While exploring water soluble rhodamine based fluorescent polymeric systems for biological imaging applications we came across new rhodamine derivatives that possess interesting optical properties. We report the synthesis of three different 2 ',7 '-diphenylated rhodamine derivatives (1-3) with distinct photophysical properties. The three rhodamine derivatives differ by the number of methyl groups present on the nitrogens and their absorption maxima are red-shifted on increased methylation. We observed an unusual inertness of these compounds toward traditional DCC-DMAP esterification conditions, which we attribute to the ease of lactonization in the presence of even minute amounts of the nucleophile/base DMAP (pK(a) = 9.2). Synthesis of acrylate esters was successfully accomplished using MSNT (1-(Mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole) coupling conditions using a much milder nucleophile/base, for example, N-methyl imidazole (pK(a) = 6.95). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.124

文献信息

• Synthesis, chemical reactivity, and photophysical properties of 2′,7′ phenylated rhodamine dyes
  作者：Arunkumar Natarajan、Eugene P. Boden、Andrew Burns、Patrick J. McCloskey、Michael J. Rishel

  DOI：10.1016/j.tetlet.2014.05.124

  日期：2014.7

  While exploring water soluble rhodamine based fluorescent polymeric systems for biological imaging applications we came across new rhodamine derivatives that possess interesting optical properties. We report the synthesis of three different 2 ',7 '-diphenylated rhodamine derivatives (1-3) with distinct photophysical properties. The three rhodamine derivatives differ by the number of methyl groups present on the nitrogens and their absorption maxima are red-shifted on increased methylation. We observed an unusual inertness of these compounds toward traditional DCC-DMAP esterification conditions, which we attribute to the ease of lactonization in the presence of even minute amounts of the nucleophile/base DMAP (pK(a) = 9.2). Synthesis of acrylate esters was successfully accomplished using MSNT (1-(Mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole) coupling conditions using a much milder nucleophile/base, for example, N-methyl imidazole (pK(a) = 6.95). (C) 2014 Elsevier Ltd. All rights reserved.