1-(2-(1-hydroxyethyl)-3,6-dimethoxyphenyl)-prop-2-en-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-(1-hydroxyethyl)-3,6-dimethoxyphenyl)-prop-2-en-1-ol
• 英文别名: (1R)-1-[2-[(1S)-1-hydroxyethyl]-3,6-dimethoxyphenyl]prop-2-en-1-ol
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: WTDCLBHVOVQJRA-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-(1-hydroxyethyl)-3,6-dimethoxyphenyl)-prop-2-en-1-ol 在 silver(II) oxide 、 palladium diacetate 、 硝酸 、 copper dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 29.5h， 生成 (3aS,5S,11bS)-5-Methyl-7-trimethylsilanyloxy-3,3a,5,6a,7,10,10a,11b-octahydro-1,4-dioxa-cyclopenta[a]anthracene-2,6,11-trione
  参考文献：
  名称：

  Direct Total Syntheses of Frenolicin B and Kalafungin via Highly Regioselective Diels-Alder Reactions

  摘要：

  Frenolicin B, an anticoccidial agent, has been synthesized in six steps from ketone 3. Racemic kalafungin, an antifungal agent, has been synthesized in five steps. The key step in both syntheses, a regioselective Diels-Alder reaction, proceeds with complete regiocontrol and in excellent yield. One rationale for the remarkable stereocontrol is that the lactone ring induces ring-puckering in the quinone subunit which, in consort with electrostatic repulsion, contributes to the regioselectivity.

  DOI：

  10.1021/jo00110a017
• 作为产物：
  描述：

  4,7-Dimethoxy-3-methyl-1,3-dihydro-2-benzofuran-1-ol 、 乙烯基氯化镁 在 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以1.76 g的产率得到1-(2-(1-hydroxyethyl)-3,6-dimethoxyphenyl)-prop-2-en-1-ol
  参考文献：
  名称：

  Total Synthesis of Crisamicin A

  摘要：

  Stereoselective total synthesis of natural product crisamicin A (1) was accomplished for the first time via the Pd/TMTU-catalyzed alkoxycarbonylative annulation to generate a unique cis-pyran-fused lactone, an intermolecular Diels-Alder reaction to construct the pyranonaphthoquinone unit, and a novel Pd-thiourea pincer complex-catalyzed homocoupling of functionalized naphthoquinones.

  DOI：

  10.1021/ol800977n

文献信息

• Total Synthesis of Crisamicin A
  作者：Zhengtao Li、Yingxiang Gao、Yefeng Tang、Mingji Dai、Guoxin Wang、Zhigang Wang、Zhen Yang

  DOI：10.1021/ol800977n

  日期：2008.7.17

  Stereoselective total synthesis of natural product crisamicin A (1) was accomplished for the first time via the Pd/TMTU-catalyzed alkoxycarbonylative annulation to generate a unique cis-pyran-fused lactone, an intermolecular Diels-Alder reaction to construct the pyranonaphthoquinone unit, and a novel Pd-thiourea pincer complex-catalyzed homocoupling of functionalized naphthoquinones.
• Direct Total Syntheses of Frenolicin B and Kalafungin via Highly Regioselective Diels-Alder Reactions
  作者：George A. Kraus、Jun Li、Mark S. Gordon、Jan H. Jensen

  DOI：10.1021/jo00110a017

  日期：1995.3

  Frenolicin B, an anticoccidial agent, has been synthesized in six steps from ketone 3. Racemic kalafungin, an antifungal agent, has been synthesized in five steps. The key step in both syntheses, a regioselective Diels-Alder reaction, proceeds with complete regiocontrol and in excellent yield. One rationale for the remarkable stereocontrol is that the lactone ring induces ring-puckering in the quinone subunit which, in consort with electrostatic repulsion, contributes to the regioselectivity.