(E)-3-(2,2-dimethyl-8-prenyl-2H-1-benzopyran-6-yl)-2-propenoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-3-(2,2-dimethyl-8-prenyl-2H-1-benzopyran-6-yl)-2-propenoic acid
• 英文别名: 2,2-dimethyl-8-prenylchromene-6-propenoicacid；culifolin；(E)-3-[2,2-dimethyl-8-(3-methylbut-2-enyl)chromen-6-yl]prop-2-enoic acid
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: ZKUFWHYBAKVWMB-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(2,2-dimethyl-8-prenyl-2H-1-benzopyran-6-yl)-2-propenoic acid 以 甲醇 为溶剂， 反应 288.0h， 生成 (Z)-3-[2,2-Dimethyl-8-(3-methyl-but-2-enyl)-2H-chromen-6-yl]-acrylic acid
  参考文献：
  名称：

  Enhanced Cytotoxicity in a Z-Photoisomer of a Benzopyran Derivative of Propolis

  摘要：

  (Z)-2,2-Dimethyl-8-(3-methyl-2-butenyl) acid (1) was isolated from Brazilian propolis, together with-the known benzopyran derivative, (E)-2,2-dimethyl-8-(3-met-2-butenyl)-benzopyran-6-propenoic acid (2). The structure was determined by spectroscopic analyses, which included 1D and 2D H-1 and C-13 NMR experiments, as well as MS, IR, and UV spectroscopy, Compound 2 rapidly changed to 1 under UV irradiation conditions (365 nm), and. the reverse reaction was also observed. The ratio of 1 to 2 reached 2.3 when the reaction began from either 1 or 2, indicating a photostationary state. Compound 1 displayed an approximate 7-fold stronger cytotoxicity against human lung carcinoma cells (HPLC-2) compared with 2.

  DOI：

  10.1021/np990463m
• 作为产物：
  描述：

  4-碘-2-(3-甲基-2-丁烯基)-苯酚 在 copper(II) choride dihydrate 、 三苯基膦双(三氟甲磺酰亚胺)金 、 palladium diacetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 46.0h， 生成 (E)-3-(2,2-dimethyl-8-prenyl-2H-1-benzopyran-6-yl)-2-propenoic acid
  参考文献：
  名称：

  Ph3PAuNTf2 作为 2H-Chromenes 选择性合成的优良催化剂：在苯并吡喃天然产物的简洁合成中的应用

  摘要：

  Ph3PAuNTf2 (≈1 mol-%) 以优异的产率催化取代的芳基炔丙基醚选择性环异构化成 2H-色烯。苯并呋喃副产物仅在缺电子芳烃的情况下形成，相对产率高达 7%。Ph3PAuNTf2 催化的芳炔基醚环化被用作简明合成天然苯并吡喃 seselin、xanthyletin、precocenes I 和 II、8-(3',3'-二甲基烯丙基)wenteria chromene 和 2, 2-二甲基-8-异戊二烯-6-丙烯酸。

  DOI：

  10.1002/ejoc.201001674

文献信息

• Inhibitory activity of Brazilian green propolis components and their derivatives on the release of cys-leukotrienes
  作者：Hiroko Tani、Keiko Hasumi、Tomoki Tatefuji、Ken Hashimoto、Hiroyuki Koshino、Shunya Takahashi

  DOI：10.1016/j.bmc.2009.11.007

  日期：2010.1

  their phenethyl esters were synthesized and evaluated as inhibitors of cys-LTs release. Artepillin C, baccharin, and kaempferide were the major active components of the ethanol extract. The inhibitory activity of artepillin C phenethyl ester was comparable to that of existing LT synthesis inhibitors.

  研究了巴西绿色蜂胶乙醇提取物对变应性鼻炎患者Cry j1诱导的cys-白三烯和组胺从外周白细胞释放的影响。提取物抗过敏特性的关键机制之一是抑制cys-LTs释放。此外，合成了一系列蜂胶成分及其苯乙基酯，并评估了它们是cys-LTs释放的抑制剂。Artepillin C，baccharin和kaempferide是乙醇提取物中的主要活性成分。青霉素C苯乙酯的抑制活性与现有的LT合成抑制剂相当。
• TYPING NATURAL PRODUCTS
  申请人：Marcucci Ribeiro, Maria Cristina

  公开号：EP1575689A2

  公开（公告）日：2005-09-21
• Typing natural products
  申请人：——

  公开号：US20040126437A1

  公开（公告）日：2004-07-01

  The present invention refers to achemical process for separation of different kinds of substances which are present in Brazilian propolis, by means of HPLC and GC-MS combined techniques. This provided a process for a HPLC separation which is able to identify the majority components of the propolis sample by using a suitable analysis software for this end.
• [EN] TYPING NATURAL PRODUCTS<br/>[FR] PROCEDE DE TYPAGE DE PRODUITS NATURELS
  申请人：MARCUCCI RIBEIRO MARIA CRISTIN

  公开号：WO2002051516A2

  公开（公告）日：2002-07-04

  The present invention refers to achemical process for separation of different kinds of substances which are present in Brazilian propolis, by means of HPLC and GC-MS combined techniques. This provided a process for a HPLC separation which is able to identify the majority components of the propolis sample by using a suitable analysis software for this end.
• Ph3PAuNTf2 as a Superior Catalyst for the Selective Synthesis of 2H-Chromenes: Application to the Concise Synthesis of Benzopyran Natural Products
  作者：Ioannis N. Lykakis、Christina Efe、Charis Gryparis、Manolis Stratakis

  DOI：10.1002/ejoc.201001674

  日期：2011.4

  Ph3PAuNTf2 (≈1 mol-%) catalyzes the selective cycloisomerization of substituted aryl propargyl ethers into 2H-chromenes in excellent yields. Benzofuran byproducts are formed only in the case of electron-deficient arenes, in up to 7 % relative yield. The Ph3PAuNTf2-catalyzed cyclization of aryl propargyl ethers was applied as a key step to the concise synthesis of the naturally occurring benzopyrans

  Ph3PAuNTf2 (≈1 mol-%) 以优异的产率催化取代的芳基炔丙基醚选择性环异构化成 2H-色烯。苯并呋喃副产物仅在缺电子芳烃的情况下形成，相对产率高达 7%。Ph3PAuNTf2 催化的芳炔基醚环化被用作简明合成天然苯并吡喃 seselin、xanthyletin、precocenes I 和 II、8-(3',3'-二甲基烯丙基)wenteria chromene 和 2, 2-二甲基-8-异戊二烯-6-丙烯酸。