(±)-3-(but-3-en-1-yl)isobenzofuran-1(3H)-one | 1438281-39-0

• 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: (±)-3-(but-3-en-1-yl)isobenzofuran-1(3H)-one
• 英文别名: 3-(but-3-en-1-yl)isobenzofuran-1(3H)-one；3-but-3-enyl-3H-2-benzofuran-1-one
• CAS: 1438281-39-0
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: ZOSCOLADEXHWEX-UHFFFAOYSA-N

物化性质

• 沸点：
  310.5±31.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (±)-3-(but-3-en-1-yl)isobenzofuran-1(3H)-one 在 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 碘苯二乙酸 、 potassium bromide 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 24.0h， 生成 spiro<(2-oxo-tetrahydrofuran)-5,3'-(1'-oxo-benzofuran)>
  参考文献：
  名称：

  通过氧化 C-H 螺环化合成 Azaspiro-γ-内酯的新合成方法

  摘要：

  报道了一种新的氮杂螺-γ-内酯合成方法。关键的 C-H 螺内酯化反应是通过使用二乙酸碘苯和溴化钾来实现的，以高产率提供各种氮杂螺-γ-内酯。该反应也适用于双内酯衍生物的制备。

  DOI：

  10.1055/s-0037-1611941
• 作为产物：
  描述：

  4-戊烯醛 、 2-碘苯甲酸甲酯 在 lithium chloro-isopropyl-magnesium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到(±)-3-(but-3-en-1-yl)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

• Pd-Catalyzed carbonylative lactonization of 2-halidearomatic aldehydes with H₂O as a nucleophile
  作者：Min Si、Jiaqi Yan、Yongzheng Ding、Hanmin Huang

  DOI：10.1039/d2ob00623e

  日期：——

  A palladium-catalyzed carbonylative cyclization reaction of 2-halidebenzaldehydes with H2O is described, which provides a strategy for the synthesis of diversely substituted 3,3′-oxyphthalides. Notably, the obtained 3,3′-oxyphthalide could be easily transformed into 3-aryl and alkyl phthalides with excellent efficiency using organozinc reagents under mild reaction conditions.

  描述了钯催化的 2-卤代苯甲醛与 H 2 O 的羰基环化反应，为合成多种取代的 3,3'-邻苯二甲酸酯提供了策略。值得注意的是，在温和的反应条件下，使用有机锌试剂，获得的 3,3'-邻苯二甲酸可以很容易地转化为 3-芳基和烷基苯二甲酸苯并具有优异的效率。
• 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.
• New Synthetic Methodology Toward Azaspiro-γ-Lactones by Oxidative C–H Spirocyclization
  作者：Hidemi Yoda、Tetsuya Sengoku、Yuichiro Nagai、Toshiyasu Inuzuka

  DOI：10.1055/s-0037-1611941

  日期：2019.1

  A new synthetic methodology for azaspiro-γ-lactones is reported. The key C–H spirolactonization was accomplished by employing iodobenzene diacetate and potassium bromide to afford a variety of azaspiro-γ-lactones in high yields. The reaction was also applicable to the preparation of a bislactone derivative.

  报道了一种新的氮杂螺-γ-内酯合成方法。关键的 C-H 螺内酯化反应是通过使用二乙酸碘苯和溴化钾来实现的，以高产率提供各种氮杂螺-γ-内酯。该反应也适用于双内酯衍生物的制备。