plicadin | 137551-37-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: plicadin
• 英文别名: 6-hydroxy-17,17-dimethyl-3,12,18-trioxapentacyclo[11.8.0.02,10.04,9.014,19]henicosa-1(13),2(10),4(9),5,7,14(19),15,20-octaen-11-one
• CAS: 137551-37-2
• 化学式: C₂₀H₁₄O₅
• 分子量: 334.328
• InChiKey: SPBFWPDNBGDCCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-Bis(N,N-diethylcarbamoyl)benzene 在 叔丁基锂 、 仲丁基锂 、 三氯化硼 、 sodium hydride 、 对甲苯磺酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 、 正戊烷 为溶剂， 反应 15.25h， 生成 plicadin
  参考文献：
  名称：

  Directed Metalation Linked to Transition Metal Catalyzed Cascade Reactions: Two Total Syntheses of Plicadin, the Alleged Coumestan fromPsoralea plicata

  摘要：

  The oxygen-rich heterocyclic compound 1-which was proposed to be the structure of plicadin, the alleged naturally occurring coumestan from the herb Psoralea plicata-was synthesized by the rational combinations of directed ortho and remote metalation reactions with cascades of Negishi, Sonogashira, Castro-Stephens, and carbamoyl Baker-Venkataraman reactions.

  DOI：

  10.1002/(sici)1521-3773(19990517)38:10<1435::aid-anie1435>3.0.co;2-b

文献信息

• Synthesis of Phenolic Coumestans via a Sequential Dehydrogenation/Oxa-Michael Addition Reaction of 2′,4′-Dihydroxyl-3-arylcoumarins
  作者：Qinfang Yan、Yi Jiang、Xianheng Song、Guoqing Lu、Qianzhong Zhang、Zhibo Du、Albert S. C. Chan、Yong Zou

  DOI：10.1021/acs.joc.2c00120

  日期：2022.5.6

  A facile and practical approach for the synthesis of natural coumestans and derivatives starting from 2′,4′-dihydroxyl-3-arylcoumarins has been developed. The process involved a seqential intramolecular dehydrogenation/oxa-Micheal reaction efficiently promoted by 1,8-diazabicyclo[5.4.0]undec-7-ene at 40 °C under metal- and ligand-free conditions with good functional group compatibility.

  已经开发了一种从 2',4'-二羟基-3-芳基香豆素开始合成天然香豆素及其衍生物的简便实用的方法。该过程涉及由 1,8-二氮杂双环[5.4.0]undec-7-ene 在 40°C 在无金属和无配体条件下有效促进的连续分子内脱氢/oxa-Micheal 反应，具有良好的官能团相容性。
• An Efficient Synthesis of Coumestrol and Coumestans by Iodocyclization and Pd-Catalyzed Intramolecular Lactonization
  作者：Tuanli Yao、Dawei Yue、Richard C. Larock

  DOI：10.1021/jo0517038

  日期：2005.11.1

  The iodocyclization of acetoxy-containing 2-(1-alkynyl)anisoles and subsequent direct palladium-catalyzed carbonylation/lactonization provide an efficient route to naturally occurring coumestan and coumestrol, and their related analogues.
• Directed Metalation Linked to Transition Metal Catalyzed Cascade Reactions: Two Total Syntheses of Plicadin, the Alleged Coumestan fromPsoralea plicata
  作者：Brian A. Chauder、Alexey V. Kalinin、Nicholas J. Taylor、Victor Snieckus

  DOI：10.1002/(sici)1521-3773(19990517)38:10<1435::aid-anie1435>3.0.co;2-b

  日期：1999.5.17

  The oxygen-rich heterocyclic compound 1-which was proposed to be the structure of plicadin, the alleged naturally occurring coumestan from the herb Psoralea plicata-was synthesized by the rational combinations of directed ortho and remote metalation reactions with cascades of Negishi, Sonogashira, Castro-Stephens, and carbamoyl Baker-Venkataraman reactions.