renealtin A

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: renealtin A
• 英文别名: 2-[(2R,4R,5R)-4-hydroxy-5-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-yl]-1-(4-hydroxy-3-methoxyphenyl)ethanone
• 化学式: C₂₁H₂₄O₇
• 分子量: 388.417
• InChiKey: LAISPMSUAQZCQJ-FIKMYACPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 renealtin A 在 吡啶 作用下， 反应 3.0h， 以0.06 mg的产率得到Acetic acid (2S,3S,5S)-2-(4-acetoxy-3-methoxy-benzyl)-5-[2-(4-acetoxy-3-methoxy-phenyl)-2-oxo-ethyl]-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Renealtins A and B, New Diarylheptanoids with a Tetrahydrofuran Ring from the Seeds of Renealmia exaltata

  摘要：

  Two new diarylheptanoids, renealtins A (1) and B (2), have been isolated from the seeds of the Brazilian medicinal plant Renealmia exaltata ("Pacova-catinga", Zingiberaceae), and their structures were elucidated by spectroscopic data. Renealtins A (1) and B (2) are the first example of naturally occurring diarylheptanoids containing a tetrahydrofuran ring.

  DOI：

  10.1021/np0104370
• 作为产物：
  描述：

  2-[(2R,4R,5R)-5-(4-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-3-methoxybenzyl)-4-hydroxytetrahydro-2-furanyl]-1-(4-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-3-methoxyphenyl)-1-ethanone 在 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到renealtin A
  参考文献：
  名称：

  A short and efficient synthesis of renealtins A and B

  摘要：

  The total syntheses of the first examples of diarylheptanoid natural products, renealtins A (1) and B (2), isolated from Renealmia exaltata are described, utilizing a delta-lactone intermediate 9. The key reactions involved are asymmetric dihydroxylation and oxy-Michael addition. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.025

文献信息

• First Asymmetric Synthesis of New Diarylheptanoids, Renealtin A and B, with a Tetrahydrofuran Ring
  作者：Hidemi Yoda、Tomoki Katoh、Daisuke Matsuura、Nobuyuki Mase、Kunihiko Takabe

  DOI：10.1055/s-2006-948168

  日期：2006.8

  An efficient and convenient process is described for the first preparation of a new diarylheptanoid, renealtin A, isolated from the seeds of the Brazilian medicinal plant Renealmia exaltata. The key trisubstituted tetrahydrofuran ring was constructed through Lewis acid mediated stereoselective allylation of the lactol derivative by featuring the elaboration of the functionalized homochiral lactone

  描述了从巴西药用植物 Reealmia exaltata 的种子中分离出的一种新的二芳基庚烷类 reealtin A 的首次制备方法，该方法有效且方便。关键的三取代四氢呋喃环是通过路易斯酸介导的内酯衍生物立体选择性烯丙基化构建的，其特征是对 L-酒石酸衍生的功能化同手性内酯进行了精心设计。还建立了其他次要立体异构体肾素 B 的合成。
• A short and efficient synthesis of renealtins A and B
  作者：Gowravaram Sabitha、K. Yadagiri、J.S. Yadav

  DOI：10.1016/j.tetlet.2007.09.025

  日期：2007.11

  The total syntheses of the first examples of diarylheptanoid natural products, renealtins A (1) and B (2), isolated from Renealmia exaltata are described, utilizing a delta-lactone intermediate 9. The key reactions involved are asymmetric dihydroxylation and oxy-Michael addition. (C) 2007 Elsevier Ltd. All rights reserved.
• Renealtins A and B, New Diarylheptanoids with a Tetrahydrofuran Ring from the Seeds of <i>Renealmia exaltata</i>
  作者：Mitsuhiro Sekiguchi、Hideyuki Shigemori、Ayumi Ohsaki、Jun'ichi Kobayashi

  DOI：10.1021/np0104370

  日期：2002.3.1

  Two new diarylheptanoids, renealtins A (1) and B (2), have been isolated from the seeds of the Brazilian medicinal plant Renealmia exaltata ("Pacova-catinga", Zingiberaceae), and their structures were elucidated by spectroscopic data. Renealtins A (1) and B (2) are the first example of naturally occurring diarylheptanoids containing a tetrahydrofuran ring.

表征谱图