5-甲氧基-2H-色烯-3-甲醛 | 57543-41-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 中文名称: 5-甲氧基-2H-色烯-3-甲醛
• 英文名称: 5-methoxy-2H-chromene-3-carbaldehyde
• CAS: 57543-41-6
• 化学式: C₁₁H₁₀O₃
• mdl: MFCD08705724
• 分子量: 190.199
• InChiKey: GYZDPWCXCAHLIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-甲氧基-2H-色烯-3-甲醛 在 manganese(IV) oxide 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.83h， 生成 2’,4’-dihydroxyphenyl-5-methoxy-2H-chromen-3-ylmethanone
  参考文献：
  名称：

  Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists

  摘要：

  Farnesoid X receptor (FXR), a nuclear receptor mainly distributed in liver and intestine, has been regarded as a potential target for the treatment of various metabolic diseases, cancer and infectious diseases related to liver. Starting from two previously identified chalcone-based FXR antagonists, we tried to increase the activity through the design and synthesis of a library containing chalcones, flavones and chromenes, based on substitution manipulation and conformation (ring closure) restriction strategy. Many chalcones and four chromenes were identified as microM potent FXR antagonists, among which chromene 11c significantly decreased the plasma and hepatic triglyceride level in KKay mice. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.037
• 作为产物：
  描述：

  2-羟基-6-甲氧基苯甲醛 在 三乙烯二胺 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 5-甲氧基-2H-色烯-3-甲醛
  参考文献：
  名称：

  Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists

  摘要：

  Farnesoid X receptor (FXR), a nuclear receptor mainly distributed in liver and intestine, has been regarded as a potential target for the treatment of various metabolic diseases, cancer and infectious diseases related to liver. Starting from two previously identified chalcone-based FXR antagonists, we tried to increase the activity through the design and synthesis of a library containing chalcones, flavones and chromenes, based on substitution manipulation and conformation (ring closure) restriction strategy. Many chalcones and four chromenes were identified as microM potent FXR antagonists, among which chromene 11c significantly decreased the plasma and hepatic triglyceride level in KKay mice. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.037

文献信息

• Synthesis of Robalzotan, Ebalzotan, and Rotigotine Precursors via the Stereoselective Multienzymatic Cascade Reduction of α,β-Unsaturated Aldehydes
  作者：Elisabetta Brenna、Francesco G. Gatti、Luciana Malpezzi、Daniela Monti、Fabio Parmeggiani、Alessandro Sacchetti

  DOI：10.1021/jo4003097

  日期：2013.5.17

  The key step is based on a multienzymatic reduction of an α,β-unsaturated aldehyde or ketone to give the saturated primary or secondary alcohol, in a high yield and with a high ee. The catalytic system consists of the combination of an ene-reductase (ER; i.e., OYE2 or OYE3 belonging to the Old Yellow Enzyme family) with an alcohol dehydrogenase (ADH), applying the in situ substrate feeding product removal

  据报道，基于四氢化萘或苯并二氢吡喃结构部分的立体选择性合成双环伯胺或仲胺。这些胺是重要的活性药物成分（如罗替戈汀（Neupro），罗巴唑坦和依巴唑坦）的前体。关键步骤是基于α，β-不饱和醛或酮的多酶还原，以高收率和高ee值得到饱和伯醇或仲醇。催化系统由烯还原酶（ER；即属于Old Yellow Enzyme家族的OYE2或OYE3）与醇脱氢酶（ADH）结合而成，采用原位底物进料产品去除技术。通过该系统，烯丙基醇副产物的形成和手性不稳定的α-取代的醛中间体的外消旋化被最小化。通过库尔修斯重排精制伯醇。OYE2与Prelog或抗Prelog ADH的组合可以制备ee> 99％和de> 87％的仲醇。通过与真实样品进行比较，明确确定了伯胺的绝对构型。通过X射线晶体结构和Mosher酯的NMR分析确定仲醇的立体化学。
• 一种苯并吡喃类化合物、及其制备方法和药物组合物与用途
  申请人：中国医学科学院药物研究所

  公开号：CN110240583A

  公开（公告）日：2019-09-17

  本发明公开了如式Ⅰ所示的苯并吡喃类化合物，苯并吡喃类化合物的制备方法，含有这类化合物的组合物以及这类化合物在制备法尼酯X受体拮抗剂、肝脏保护剂、防治高血脂、防治2型糖尿病的药物中的用途。
• Productivity enhancement of CC bioreductions by coupling the in situ substrate feeding product removal technology with isolated enzymes
  作者：Elisabetta Brenna、Francesco G. Gatti、Daniela Monti、Fabio Parmeggiani、Alessandro Sacchetti

  DOI：10.1039/c1cc16014a

  日期：——

  To overcome the usually low productivities of the CC bond bioreduction of α,β-unsaturated aldehydes we combined the in situ substrate feeding product removal (SFPR) technology with a cascade system comprising an isolated ene-reductase and a chemoselective alcohol dehydrogenase.

  为了克服α、β-不饱和醛的 CC 键生物还原中通常存在的低生产率问题，我们将原位底物进料产物去除（SFPR）技术与由分离的烯还原酶和化学选择性醇脱氢酶组成的级联系统相结合。
• Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists
  作者：Guoning Zhang、Shuainan Liu、Wenjuan Tan、Ruchi Verma、Yuan Chen、Deyang Sun、Yi Huan、Qian Jiang、Xing Wang、Na Wang、Yang Xu、Chiwai Wong、Zhufang Shen、Ruitang Deng、Jinsong Liu、Yanqiao Zhang、Weishuo Fang

  DOI：10.1016/j.ejmech.2017.02.037

  日期：2017.3

  Farnesoid X receptor (FXR), a nuclear receptor mainly distributed in liver and intestine, has been regarded as a potential target for the treatment of various metabolic diseases, cancer and infectious diseases related to liver. Starting from two previously identified chalcone-based FXR antagonists, we tried to increase the activity through the design and synthesis of a library containing chalcones, flavones and chromenes, based on substitution manipulation and conformation (ring closure) restriction strategy. Many chalcones and four chromenes were identified as microM potent FXR antagonists, among which chromene 11c significantly decreased the plasma and hepatic triglyceride level in KKay mice. (C) 2017 Elsevier Masson SAS. All rights reserved.