5-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1H-pyrrole-2-carbaldehyde | 1337989-73-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1H-pyrrole-2-carbaldehyde
• 英文别名: 5-(oxan-2-yloxymethyl)-1H-pyrrole-2-carbaldehyde
• CAS: 1337989-73-7
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: ROPXKMOFKYFQLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1H-pyrrole-2-carbaldehyde 在 盐酸 、 戴斯-马丁氧化剂 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 55.0h， 生成 xylapyrroside B
  参考文献：
  名称：

  Xylapyrrosides A and B, two rare sugar-morpholine spiroketal pyrrole-derived alkaloids from Xylaria nigripes: isolation, complete structure elucidation, and total syntheses

  摘要：

  Two new [named xylapyrrosides A (1) and B (2)1 along with two known [pollenopyrrosides A (3) and B (=acortatarin A, 4)] naturally occurring spirocyclic pyrrole alkaloids were isolated and identified as minor components from the Et0H extract of the dried mycelia of the edible medicinal fungus Xylaria nigripes. Their structures were established by a combination of interpretation of spectroscopic data and single-crystal X-ray diffraction analyses. The isolates possess a unique tricyclic skeleton comprising a common bicyclic 2-formyl-pyrrole-fused morpholine, with a variable ketohexoside ring. This class of alkaloids is quite rare from natural sources. In this study, the total syntheses of compounds 1, 2 and 4 were successfully achieved by two alternative strategies, and three new analogs [named xylapyrrosides A(1) (1a), A(2) (1b) and B-1 (2a)] were also produced. Notably, the total synthesis of such spiroketal alkaloids with a pyranose ring (e.g.,1) was accomplished for the first time. The absolute configurations of the new isolates can be thereafter unequivocally secured by the total syntheses. The above isolated and synthesized spiro-alkaloids were found to show moderate antioxidant effects by preventing the oxidative stress-induced cytotoxicity of A7r5 rat vascular smooth muscle cells (VSMCs). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.020
• 作为产物：
  描述：

  1H-吡咯-2,5-二甲醛 在 sodium tetrahydroborate 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.25h， 生成 5-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1H-pyrrole-2-carbaldehyde
  参考文献：
  名称：

  Acortatarins A和B的全合成和立体化学修饰

  摘要：

  通过使用容易获得的d-糖描述了第一步的全合成的角蛋白A，B和对映体结构的对映体。这种聚合的总合成揭示了对阿考塔林A的绝对构型的修订和对阿考塔林B的结构的修订。涉及的关键步骤是用去质子化的2，5-二取代的吡咯进行的区域选择性环氧化物的开环和螺缩酮化。

  DOI：

  10.1021/ol202121k

文献信息

• 天然产物Xylapyr roside A的选择性合成方法
  申请人：复旦大学

  公开号：CN105859745B

  公开（公告）日：2018-05-25

  本发明属化学合成领域，涉及天然产物Xylapyrroside A的选择性合成方法。本发明以(R)‑(+)‑2,2‑二甲基‑1,3‑二氧戊环‑4‑甲醛为起始原料，经过格氏反应、羟基的苄基保护、脱叉酮保护、两羟基选择性的叔丁基二甲硅基和苄基保护、末端双键环氧化及碘代开环以及氧化得到(4S,5R)‑4,5‑双苄氧基‑6‑叔丁基二甲基硅氧基‑1‑碘代戊烷‑2‑酮与另一中间体5‑(((四氢‑2H‑吡喃‑2‑基)氧)甲基)‑1H‑吡咯‑2‑甲醛经碱性条件下缩合及酸性条件下脱保护同时环合，最后合成目标产物。本发明操作简便，收率较高，且试剂原料廉价易得。
• Total Synthesis and Stereochemical Revision of Acortatarins A and B
  作者：Gangarajula Sudhakar、Vilas D. Kadam、Shruthi Bayya、Gavinolla Pranitha、Bharatam Jagadeesh

  DOI：10.1021/ol202121k

  日期：2011.10.21

  A first total synthesis of acortatarins A, B, and an enantiomer of the proposed structure of acortatarin B is described by using readily available d-sugars. This convergent total synthesis revealed the revision of the absolute configuration of acortatarin A and structural revision of acortatarin B. The key steps involved are regioselective epoxide opening with deprotonated 2,5-disubstituted pyrrole

  通过使用容易获得的d-糖描述了第一步的全合成的角蛋白A，B和对映体结构的对映体。这种聚合的总合成揭示了对阿考塔林A的绝对构型的修订和对阿考塔林B的结构的修订。涉及的关键步骤是用去质子化的2，5-二取代的吡咯进行的区域选择性环氧化物的开环和螺缩酮化。
• 吡咯并吗啉螺环生物碱类化合物及其制备方法和用途
  申请人：复旦大学

  公开号：CN105884845A

  公开（公告）日：2016-08-24

  本发明属药学领域，涉及式Ⅰ结构的吡咯并吗啉螺环生物碱类化合物及其在制备抗氧化应激，治疗心血管疾病药物中的新用途，同时还涉及所述化合物的提取和制备方法。本发明的化合物可从中药乌灵菌粉中提取分离得到或化学合成获得，经试验结果表明，本发明的化合物对氧化应激所产生的细胞损伤具有保护作用，可用于制备治疗心血管等疾病的药物；所述化合物可进一步制备抗氧化药物和制剂，包括注射、口服药物和外用药物等剂型的抗氧化药物。其中，9位和11位构型为R或者S。
• Concise Total Synthesis of Acortatarin A
  作者：Takaaki TERANISHI、Masayuki KAGEYAMA、Shigefumi KUWAHARA

  DOI：10.1271/bbb.120862

  日期：2013.3.23

  The spirocyclic pyrrole alkaloid, acortatarin A, which had been isolated from a Chinese medicinal plant, was synthesized from a known olefinic compound by a concise six-step sequence involving N-alkylation of a pyrrole derivative with an a-bromo ketone intermediate as the key step.
• Xylapyrrosides A and B, two rare sugar-morpholine spiroketal pyrrole-derived alkaloids from Xylaria nigripes: isolation, complete structure elucidation, and total syntheses
  作者：Ming Li、Juan Xiong、Ya Huang、Li-Jun Wang、Yu Tang、Guo-Xun Yang、Xin-Hua Liu、Bang-Guo Wei、Hui Fan、Yun Zhao、Wen-Zhu Zhai、Jin-Feng Hu

  DOI：10.1016/j.tet.2015.06.020

  日期：2015.8

  Two new [named xylapyrrosides A (1) and B (2)1 along with two known [pollenopyrrosides A (3) and B (=acortatarin A, 4)] naturally occurring spirocyclic pyrrole alkaloids were isolated and identified as minor components from the Et0H extract of the dried mycelia of the edible medicinal fungus Xylaria nigripes. Their structures were established by a combination of interpretation of spectroscopic data and single-crystal X-ray diffraction analyses. The isolates possess a unique tricyclic skeleton comprising a common bicyclic 2-formyl-pyrrole-fused morpholine, with a variable ketohexoside ring. This class of alkaloids is quite rare from natural sources. In this study, the total syntheses of compounds 1, 2 and 4 were successfully achieved by two alternative strategies, and three new analogs [named xylapyrrosides A(1) (1a), A(2) (1b) and B-1 (2a)] were also produced. Notably, the total synthesis of such spiroketal alkaloids with a pyranose ring (e.g.,1) was accomplished for the first time. The absolute configurations of the new isolates can be thereafter unequivocally secured by the total syntheses. The above isolated and synthesized spiro-alkaloids were found to show moderate antioxidant effects by preventing the oxidative stress-induced cytotoxicity of A7r5 rat vascular smooth muscle cells (VSMCs). (C) 2015 Elsevier Ltd. All rights reserved.