[(1R,2S,5S)-5-[2,6-二羟基-4-(6-羟基-1-苯并呋喃-2-基)苯基]-2-(2,4-二羟基苯基)-3-甲基-1-环己-3-烯基]-[2,4-二羟基-3-(3-甲基丁-2-烯基)苯基]甲酮 | 76472-89-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 中文名称: [(1R,2S,5S)-5-[2,6-二羟基-4-(6-羟基-1-苯并呋喃-2-基)苯基]-2-(2,4-二羟基苯基)-3-甲基-1-环己-3-烯基]-[2,4-二羟基-3-(3-甲基丁-2-烯基)苯基]甲酮
• 英文名称: chalcomoracin
• 英文别名: [(1R,2S,6S)-2-[2,6-dihydroxy-4-(6-hydroxy-1-benzofuran-2-yl)phenyl]-6-(2,4-dihydroxyphenyl)-4-methylcyclohex-3-en-1-yl]-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]methanone
• CAS: 76472-89-4
• 化学式: C₃₉H₃₆O₉
• 分子量: 648.709
• InChiKey: SEHVRKPXIDOTRX-QQDDVHTNSA-N

物化性质

• 沸点：
  836.3±65.0 °C(Predicted)
• 密度：
  1.380±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  48
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  172
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(1R,2S,5S)-5-[2,6-二羟基-4-(6-羟基-1-苯并呋喃-2-基)苯基]-2-(2,4-二羟基苯基)-3-甲基-1-环己-3-烯基]-[2,4-二羟基-3-(3-甲基丁-2-烯基)苯基]甲酮 生成 (1R,9S,13S,21R)-1-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-17-(6-hydroxy-1-benzofuran-2-yl)-11-methyl-2,20-dioxapentacyclo[11.7.1.03,8.09,21.014,19]henicosa-3(8),4,6,11,14,16,18-heptaene-5,15-diol
  参考文献：
  名称：

  HANO, YOSHIO;SUZUKI, SHINKICHI;NOMURA, TARO;IITAKA, YOICHI, HETEROCYCLES, 27,(1988) N0, C. 2315-2325

  摘要：

  DOI：
• 作为产物：
  描述：

  <2-13C>cinnamic acid 以 乙醇 、 水 为溶剂， 反应 168.0h， 以30 mg的产率得到[(1R,2S,5S)-5-[2,6-二羟基-4-(6-羟基-1-苯并呋喃-2-基)苯基]-2-(2,4-二羟基苯基)-3-甲基-1-环己-3-烯基]-[2,4-二羟基-3-(3-甲基丁-2-烯基)苯基]甲酮
  参考文献：
  名称：

  Hano, Yoshio; Shimazaki, Manabu; Nomura, Taro, Heterocycles, 1999, vol. 50, # 2, p. 989 - 994

  摘要：

  DOI：

文献信息

• Mulberry Diels−Alder Adducts: Synthesis of Chalcomoracin and Mulberrofuran C Methyl Ethers
  作者：Christian Gunawan、Mark A. Rizzacasa

  DOI：10.1021/ol9026705

  日期：2010.4.2

  heptamethyl ethers of the mulberry Diels−Alder adducts chalcomoracin (1) and mulberrofuran J (2) is described. The key steps in each approach involved a biomimetic intermolecular [4+2]-cycloaddition between a dehydroprenylphenol diene derived from an isoprenoid-substituted phenolic compound and an α,β-unsaturated alkene of a chalcone as the dienophile. Critical to the success of the Diels−Alder reaction

  描述了桑树Diels-Alder加合物查库拉霉素（1）和桑fur呋喃J（2）的每种七甲基醚的合成。每种方法的关键步骤都涉及到由异戊二烯基取代的酚类化合物衍生的脱氢异戊二烯基苯酚二烯与查耳酮的α，β-不饱和烯烃作为亲二烯体之间的仿生分子间[4 + 2]-环加成反应。Diels-Alder反应成功的关键是2'-羟基查耳酮中存在游离酚。
• Synthetic studies towards the mulberry Diels–Alder adducts: H-bond accelerated cycloadditions of chalcones
  作者：Sompong Boonsri、Christian Gunawan、Elizabeth H. Krenske、Mark A. Rizzacasa

  DOI：10.1039/c2ob25115a

  日期：——

  The methyl ether derivatives 2, 4 and 6 of the mulberry Diels–Alder adducts chalcomoracin (1) and mulberrofuran C (3) and kuwanon J (5) respectively have been synthesized by a thermal [4 + 2]-cycloaddition reaction between a chalcone and dehydroprenyl diene. A H-bonded ortho OH substituent on the chalcone was found to be essential for Diels–Alder reactivity. Density functional theory calculations show that the OH group lowers the barrier for the Diels–Alder reaction by 2–3 kcal mol−1 compared with OMe. The acceleration by the OH group is traced to two transition-state effects: a stronger diene–chalcone interaction and better planarity of the aryl–diene unit.

  桑树Diels-Alder加合物白果草素（1）、桑酮C（3）和桑酮J（5）的甲基醚衍生物2、4和6分别通过查耳酮与脱氢 prenyl diene之间的热[4 + 2]环加成反应合成。研究发现，查耳酮上形成氢键的邻位羟基取代基对于Diels-Alder反应性至关重要。密度泛函理论计算表明，与甲氧基相比，羟基可将Diels-Alder反应的能垒降低2-3千卡/摩尔。羟基的加速作用归因于两种过渡态效应：更强的二烯-查耳酮相互作用和更好的芳基-二烯单元平面性。
• COMPOSITIONS AND METHODS FOR MANAGING WEIGHT
  申请人：Unigen, Inc.

  公开号：US20140004215A1

  公开（公告）日：2014-01-02

  The present disclosure provides Diels-Alder adducts of chalcone and prenylphenyl moieties capable of modulating the activity of cannabinoid receptors, and to oligomers of flavan-3-ol capable of modulating fat absorption and storage. Such Diels-Alder adducts of chalcone and prenylphenyl moieties or oligomers of flavan-3-ol can optionally be used in combination with other weight management agents, such as anorectic agents, a lipase inhibitors, other cannabinoid receptor modulators, psychotropic agents, insulin sensitizers, stimulants, or satiety agents, as well as to methods of use thereof such as treating or preventing weight gain or obesity, promoting weight loss, appetite suppression, modifying satiety, or the like.

  本公开提供了香豆素和异戊烯基苯基基团的Diels-Alder加合物，能够调节大麻素受体的活性，以及能够调节脂肪吸收和储存的黄烷类三酚寡聚体。这些香豆素和异戊烯基苯基团的Diels-Alder加合物或黄烷类三酚寡聚体可以选择性地与其他减重药物联合使用，例如厌食剂、脂肪酶抑制剂、其他大麻素受体调节剂、精神药物、胰岛素敏感剂、兴奋剂或饱腹感剂，以及使用方法，例如治疗或预防体重增加或肥胖，促进减肥，抑制食欲，调节饱腹感等。
• DIELS-ALDERASE AND USE THEREOF
  申请人：Peking University

  公开号：EP3825398A1

  公开（公告）日：2021-05-26

  The present invention provides a Diels-Alderase and use thereof, and belongs to the field of gene engineering technology. The Diels-Alderase is MaDA, and its amino acid sequence and gene sequence are represented by SEQ ID Nos. 1 and 2, respectively. The present invention also provides MaDA-1 and MaDA-2, both of which are homologous proteins of MaDA, and their amino acid sequences are represented by SEQ ID Nos. 10 and 12, respectively. The present invention has discovered that MaDA and its homologous proteins from Morus alba can stereospecifically synthesize natural products of endo configuration, and prepare D-A type natural products and their analogs in vitro using chalcones and dehydroprenyl-containing compounds as substrates, which helps to develop and utilize the medicinal value of such natural products, and also provides a possibility to synthesize other six-membered ring-containing important chemical precursors or natural products.

  本发明提供了一种 Diels-AlderaSE 及其用途，属于基因工程技术领域。该 Diels-AlderaSE 为 MaDA，其氨基酸序列和基因序列分别由 SEQ ID 编号 1 和 2 表示。本发明还提供了 MaDA-1 和 MaDA-2，它们都是 MaDA 的同源蛋白，其氨基酸序列分别由 SEQ ID 编号 10 和 12 表示。本发明发现，桑白皮中的MaDA及其同源蛋白可以立体定向合成内构型天然产物，并以查耳酮和含脱氢丙烯基化合物为底物，体外制备D-A型天然产物及其类似物，有助于开发和利用此类天然产物的药用价值，同时也为合成其他含六元环的重要化学前体或天然产物提供了可能。
• Compositions and methods for managing or improving bone disorders, joint disorders, cartilage disorders, or a combination thereof
  申请人：Unigen, Inc.

  公开号：US10583161B2

  公开（公告）日：2020-03-10

  Compositions and methods for bone health, cartilage health or both, are disclosed that include preparing and utilizing a mixture of at least one Morus extract enriched for one or more prenylated flavonoids, at least one Scutellaria extract enriched for one or more free-B-ring flavonoids, and at least one Acacia extract enriched for one or more flavans.

  已公开的用于骨骼健康、软骨健康或两者的组合物和方法包括制备和使用至少一种富含一种或多种前炔基黄酮的桑树提取物、至少一种富含一种或多种游离 B 环黄酮的黄芩提取物和至少一种富含一种或多种黄烷的金合欢提取物的混合物。