(±)-chrycolide | 91362-91-3

• 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: (±)-chrycolide
• 英文别名: Chrycolide；7-Hydroxy-3-(thiophen-2-yl)isobenzofuran-1(3H)-one；7-hydroxy-3-thiophen-2-yl-3H-2-benzofuran-1-one
• CAS: 91362-91-3
• 化学式: C₁₂H₈O₃S
• 分子量: 232.26
• InChiKey: CLGIBOHWUJNNKL-UHFFFAOYSA-N

物化性质

• 沸点：
  432.6±45.0 °C(Predicted)
• 密度：
  1.468±0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  115-116°C

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (±)-chrycolide 生成 (+/-)-chrycolide methyl eter
  参考文献：
  名称：

  TADA, MASAHIRO;CHIBA, KAZUHIRO, AGR. AND BIOL. CHEM., 1984, 48, N 5, 1367-1369

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氟-6-碘苯甲酸 在 lithium chloro-isopropyl-magnesium chloride 、 草酰氯 、 硫酸 、 四丁基氟化铵 、 magnesium sulfate 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (±)-chrycolide
  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

• Tada, Masahiro; Chiba, Kazuhiro, Agricultural and Biological Chemistry, 1984, vol. 48, # 5, p. 1367 - 1370
  作者：Tada, Masahiro、Chiba, Kazuhiro

  DOI：——

  日期：——
• Tada, Masahiro; Chiba, Kazuhiro, Agricultural and Biological Chemistry, <hi>1984</hi>, vol. 48, # 5, p. 1367 - 1370
  作者：Tada, Masahiro、Chiba, Kazuhiro

  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.
• TADA, MASAHIRO;CHIBA, KAZUHIRO, AGR. AND BIOL. CHEM., 1984, 48, N 5, 1367-1369
  作者：TADA, MASAHIRO、CHIBA, KAZUHIRO

  DOI：——

  日期：——