2-isopropenyl-2,3-dihydrofuro[3,2-g]benzopyran-7-one | 32375-25-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-isopropenyl-2,3-dihydrofuro[3,2-g]benzopyran-7-one
• 英文别名: (+)-isoangenomalin；(S)-ammirin；ent-ammirin；2-(Prop-1-EN-2-YL)-2H,3H,7H-furo[3,2-G]chromen-7-one；(2S)-2-prop-1-en-2-yl-2,3-dihydrofuro[3,2-g]chromen-7-one
• CAS: 32375-25-0
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: VMWUHWZFDITAOL-NSHDSACASA-N

物化性质

• 沸点：
  388.3±42.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-isopropenyl-2,3-dihydrofuro[3,2-g]benzopyran-7-one 在 间氯过氧苯甲酸 作用下， 以 苯 为溶剂， 生成 (S)-2-((S)-2-Methyl-oxiranyl)-2,3-dihydro-furo[3,2-g]chromen-7-one 、 (S)-2-((R)-2-Methyl-oxiranyl)-2,3-dihydro-furo[3,2-g]chromen-7-one
  参考文献：
  名称：

  Coumarins from Ferulago capillaris and F. brachyloba

  摘要：

  Four new coumarins, (+)-senecioylprangol, (-)-3 '-senecioyloxymarmesin, (+)-3 '-hydroxyprantschimgin and (+)-2"-senecioyloxymarmesin, besides 12 known coumarins have been isolated from two Ferulago species. Their structures have been established by spectroscopic methods and partial synthesis. New synthetic 3'-oxocoumarins are also described. There is a remarkable difference in the contents of the most abundant coumarins found in the roots of both species: osthol and aurapten are specific to F. capillaris and F. brachyloba, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00524-5
• 作为产物：
  描述：

  异紫花前胡素当归酯 在 氯化亚砜 、 sodium carbonate 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 2-isopropenyl-2,3-dihydrofuro[3,2-g]benzopyran-7-one
  参考文献：
  名称：

  Coumarins from Ferulago capillaris and F. brachyloba

  摘要：

  Four new coumarins, (+)-senecioylprangol, (-)-3 '-senecioyloxymarmesin, (+)-3 '-hydroxyprantschimgin and (+)-2"-senecioyloxymarmesin, besides 12 known coumarins have been isolated from two Ferulago species. Their structures have been established by spectroscopic methods and partial synthesis. New synthetic 3'-oxocoumarins are also described. There is a remarkable difference in the contents of the most abundant coumarins found in the roots of both species: osthol and aurapten are specific to F. capillaris and F. brachyloba, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00524-5

文献信息

• Absolute Structures of Some Naturally Occurring Isopropenyldihydrobenzofurans, Remirol, Remiridiol, Angenomalin, and Isoangenomalin
  作者：Seiji Yamaguchi、Shizuko Muro、Masahide Kobayashi、Masahiro Miyazawa、Yoshiro Hirai

  DOI：10.1021/jo034396j

  日期：2003.8.1

  (DHQD)(2)AQN gave the corresponding chiral 2-isopropenyl-2,3-dihydrobenzofurans. Chiral (S)-(+)-4 (99% ee, using (DHQD)(2)AQN) was converted to natural remirol (S)-(+)-1a and then to natural remiridiol (S)-(+)-1b. (S)-(+)-8 (97% ee, using (DHQD)(2)AQN) was converted to natural angenomalin (S)-(+)-2. (R)-(-)-11c (>99% ee, using (DHQ)(2)AQN), was converted to natural isoangenomalin (R)-(+)-3. Thus, the absolute

  一些天然存在的手性2-异丙烯基-2,3-二氢苯并呋喃，（+）-镜像醇（1a），（+）-反丙二醇（1b），（+）-血管内皮素（2）和（+）-的绝对结构异Angenomalin（3），通过各自的手性合成进行了研究。外消旋2-异丙烯基-2,3-二氢苯并呋喃，2-异丙烯基-4,6-二甲氧基-2,3-二氢苯并呋喃的动力学拆分（4），4-羟基-2-异丙烯基-2,3-二氢苯并呋喃-5-甲醛（8）和2-异丙烯基-6-（MOM）氧基-2,3-二氢苯并呋喃-5-甲醛（11c），使用（DHQ）（2）AQN或（DHQD）（2）AQN通过Sharpless二羟基化反应制得相应的手性2-异丙烯基-2,3-二氢苯并呋喃。将手性（S）-（+）-4（99％ee，使用（DHQD）（2）AQN）转化为天然视黄醇（S）-（+）-1a，然后转化为天然雷米洛二醇（S）-（+） -1b。（S）-（+）-8（97％ee，使用（DHQD）
• Coumarins from Ferulago capillaris and F. brachyloba
  作者：Benedicto Jiménez、Marı́a Concepción Grande、Josefa Anaya、Pascual Torres、Manuel Grande

  DOI：10.1016/s0031-9422(99)00524-5

  日期：2000.4

  Four new coumarins, (+)-senecioylprangol, (-)-3 '-senecioyloxymarmesin, (+)-3 '-hydroxyprantschimgin and (+)-2"-senecioyloxymarmesin, besides 12 known coumarins have been isolated from two Ferulago species. Their structures have been established by spectroscopic methods and partial synthesis. New synthetic 3'-oxocoumarins are also described. There is a remarkable difference in the contents of the most abundant coumarins found in the roots of both species: osthol and aurapten are specific to F. capillaris and F. brachyloba, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.