(E)-3-(2,3-dihydrobenzofuran-5-yl)acrylaldehyde

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (E)-3-(2,3-dihydrobenzofuran-5-yl)acrylaldehyde
• 英文别名: 3-(2,3-Dihydrobenzofuran-5-yl)acrylaldehyde；(E)-3-(2,3-dihydro-1-benzofuran-5-yl)prop-2-enal
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: KENRJRQZQGCSKF-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-二氢苯并呋喃 、 丙醛 在 dipotassium peroxodisulfate 、 palladium diacetate 、 三氟乙酸 、 β-丙氨酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以53%的产率得到(E)-3-(2,3-dihydrobenzofuran-5-yl)acrylaldehyde
  参考文献：
  名称：

  Dehydrogenative β-Arylation of Saturated Aldehydes Using Transient Directing Groups

  摘要：

  An unprecedented cross-dehydrogenative-coupling (CDC) reaction of saturated aldehyde beta-C-H with arenes to form cinnamaldehydes via the cleavages of four C-H bonds has been developed. The reaction possesses complete E-stereoselectivity for the C = C double bond. The protocol is featured by atom and step economy, mild reaction conditions, and convenient operation.

  DOI：

  10.1021/acs.orglett.9b00695

文献信息

• Process for Production of Optically Active Amine Derivatives
  申请人：Urayama Shinichi

  公开号：US20090036521A1

  公开（公告）日：2009-02-05

  An industrial process for production of high-purity optically active amine derivatives in high yield while inhibiting the formation of by-products, which comprises subjecting (E)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)ethylamine to asymmetric reduction, catalytically reducing the obtained product at a reaction temperature of 40 to 100° C. and a pH of 3 to 9, subjecting the obtained (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine to propionylation, and then crystallizing the reaction mixture.

  一种工业过程，用于高产率制备高纯度光学活性胺衍生物，同时抑制副产物的形成，包括将（E）-2-（1,6,7,8-四氢-2H-茚并[5,4-b]呋喃-8-基）乙基胺进行不对称还原，催化还原所得产物在反应温度为40至100°C和pH为3至9的条件下，将所得的（S）-2-（1,6,7,8-四氢-2H-茚并[5,4-b]呋喃-8-基）乙基胺进行丙酰化，然后结晶反应混合物。
• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE AMINE DERIVATIVES
  申请人：Urayama Shinichi

  公开号：US20120088826A1

  公开（公告）日：2012-04-12

  An industrial process for production of high-purity optically active amine derivatives in high yield while inhibiting the formation of by-products, which comprises subjecting (E)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)ethylamine to asymmetric reduction, catalytically reducing the obtained product at a reaction temperature of 40 to 100° C. and a pH of 3 to 9, subjecting the obtained (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine to propionylation, and then crystallizing the reaction mixture.

  一种工业过程，用于高产量地生产高纯度的光学活性胺衍生物，同时抑制副产物的形成，包括将（E）-2-（1,6,7,8-四氢-2H-茚并[5,4-b]呋喃-8-亚基）乙胺经过不对称还原，催化还原所得产物在反应温度为40至100°C和pH为3至9的条件下，将所得的（S）-2-（1,6,7,8-四氢-2H-茚并[5,4-b]呋喃-8-基）乙胺进行丙酰化，然后结晶反应混合物。
• 6-membered aza-heterocyclic containing delta-opioid receptor modulating compounds, methods of using and making the same
  申请人：Trevena, Inc.

  公开号：US10246436B2

  公开（公告）日：2019-04-02

  The present embodiments are directed, in part, to compounds, or pharmaceutically acceptable salts thereof, or pharmaceutical compositions thereof for modulating the activity of delta opioid receptor, biased and/or unbiased, and/or methods for treating pain, migraines, headaches, depression, Parkinsons Disease, anxiety, and/or overactive bladder, and other disorders and conditions described herein or any combination thereof.

  本发明的实施方案部分涉及用于调节δ阿片受体活性的化合物或其药学上可接受的盐，或其药物组合物，偏向和/或不偏向，和/或用于治疗疼痛、偏头痛、头痛、抑郁症、帕金森病、焦虑和/或膀胱过度活动症，以及本文所述的其他疾病和病症或其任意组合的方法。
• 6-MEMBERED AZA-HETEROCYCLIC CONTAINING DELTA-OPIOID RECEPTOR MODULATING COMPOUNDS, METHODS OF USING AND MAKING THE SAME
  申请人：Trevena, Inc.

  公开号：EP3344248A1

  公开（公告）日：2018-07-11
• US8097737B2
  申请人：——

  公开号：US8097737B2

  公开（公告）日：2012-01-17