Ethanamine, 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)- | 1029134-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: Ethanamine, 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)-
• 英文别名: 2-(1,2,6,7-tetrahydrocyclopenta[e][1]benzofuran-8-ylidene)ethanamine
• CAS: 1029134-74-4
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: RYYNBBSULBXPJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Ethanamine, 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)- 在 盐酸 、 四(三苯基膦)钯 、 溴 、 sodium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 4.17h， 生成 N-(2-[7-(2-methoxyphenyl)-1,6-dihydro-2H-indeno[5,4-b]-furan-8-yl]ethyl)acetamide
  参考文献：
  名称：

  1,6-Dihydro-2H-indeno[5,4-b]furan Derivatives: Design, Synthesis, and Pharmacological Characterization of a Novel Class of Highly Potent MT₂-Selective Agonists

  摘要：

  A novel series of 1,6-dihydro-2H-indeno[5,4-b]furan derivatives were designed and synthesized as MT2-selective ligands. This scaffold was identified as a potent mimic of the 5-methoxy indole core of melatonin, and introduction of a cyclohexylmethyl group at the 7-position of this scaffold afforded an MT2-selective ligand 15 (K-i = 0.012 nM) with high MT1/MT2 selectivity (799). Compound 15 was identified as a potent full agonist for the MT2 subtype and exhibited reentrainment effects to a new light/dark cycle in ICR mice at 3-30 mg/kg. This result demonstrated the involvement of the MT2 receptors in chronobiotic activity.

  DOI：

  10.1021/jm200221q
• 作为产物：
  描述：

  2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile 在 氨 、 氢气 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 Ethanamine, 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)-
  参考文献：
  名称：

  1,6-Dihydro-2H-indeno[5,4-b]furan Derivatives: Design, Synthesis, and Pharmacological Characterization of a Novel Class of Highly Potent MT₂-Selective Agonists

  摘要：

  A novel series of 1,6-dihydro-2H-indeno[5,4-b]furan derivatives were designed and synthesized as MT2-selective ligands. This scaffold was identified as a potent mimic of the 5-methoxy indole core of melatonin, and introduction of a cyclohexylmethyl group at the 7-position of this scaffold afforded an MT2-selective ligand 15 (K-i = 0.012 nM) with high MT1/MT2 selectivity (799). Compound 15 was identified as a potent full agonist for the MT2 subtype and exhibited reentrainment effects to a new light/dark cycle in ICR mice at 3-30 mg/kg. This result demonstrated the involvement of the MT2 receptors in chronobiotic activity.

  DOI：

  10.1021/jm200221q

文献信息

• [EN] PROCESS FOR THE PREPARATION OF RAMELTEON<br/>[FR] PROCÉDÉ DE PRÉPARATION DE RAMELTÉON
  申请人：WATSON PHARMA PRIVATE LTD

  公开号：WO2010055481A1

  公开（公告）日：2010-05-20

  Disclosed herein is a process for resolving N-[2-(1, 6, 7, 8-tetrahydro-2H-indeno [5, 4-b] furan-8-yl)] ethylamine into its isomers using an optically active acid and a process for preparing ramelteon from the resolved isomer.

  本文揭示了一种使用光学活性酸将N-[2-(1,6,7,8-四氢-2H-茚并[5,4-b]呋喃-8-基)]乙胺分离成其异构体的过程，以及从分离的异构体制备拉美替嗪的过程。
• Bicyclic compounds and pharmaceutical composition containing tricyclic compound for treating or preventing sleep disorders
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1199304A1

  公开（公告）日：2002-04-24

  A compound having the following general fomula: wherein R1 is an optionally substituted hydrocarbon, amino or heterocyclic group; R2 is H or an optionally substituted hydrocarbon group; R3 is H or an optionally substituted hydrocarbon or heterocyclic group; X is CHR4, NR4, O or S in which R4 is H or an optionally substituted hydrocarbon group; R5 is H, a halogen atom, C1-6 alkyl group, a C1-6 alkoxy group, a hydroxy group, a nitro group, a cyano group or an amino group wherein the C1-6 alkyl group, the C1-6 alkoxy group and the amino group may be substituted by 1 to 5 substituents, Y is C or N; ring B is an optionally substituted benzene ring; m = 1 to 4 and n = 0 to 2; L represents a leaving group such as a halogen atom, an alkylsulfonyl group, an alkylsulfonlyoxy group and arylsulfonyloxy group; or a salt thereof.

  具有以下一般式的化合物： 其中R1是可选择取代的碳氢化合物、氨基或杂环基团；R2是H或可选择取代的碳氢基团；R3是H或可选择取代的碳氢基团或杂环基团；X是CHR4、NR4、O或S，其中R4是H或可选择取代的碳氢基团；R5是H、卤素原子、C1-6烷基基团、C1-6烷氧基团、羟基、硝基、氰基或氨基，其中C1-6烷基基团、C1-6烷氧基团和氨基可能被1至5个取代基取代，Y是C或N；环B是可选择取代的苯环；m = 1至4，n = 0至2；L代表离去基团，如卤素原子、烷基磺酰基团、烷基磺酰氧基团和芳基磺酰氧基团；或其盐。
• PROCESS FOR THE PREPARATION OF RAMELTEON
  申请人：Lenna Roberto

  公开号：US20100234622A1

  公开（公告）日：2010-09-16

  A process is described for the preparation on an industrial scale of N-[2-(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]propionamide, ramelteon, having the structure illustrated below:

  描述了一种工业规模制备N-[2-(8S)-1,6,7,8-四氢-2H-茚并[5,4-b]呋喃-8-基]乙基]丙酰胺，拉莫特嗪，具有下图所示结构的过程。
• [EN] PROCESS FOR THE PREPARATION OF RAMELTEON<br/>[FR] PROCÉDÉ DE PRÉPARATION DU RAMELTÉON
  申请人：IND CHIMICA SRL

  公开号：WO2010103553A1

  公开（公告）日：2010-09-16

  A process is described for the preparation on an industrial scale of N-[2-(8S)- 1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl] propionamide, ramelteon, having the structure illustrated below: (I).

  描述了一种工业规模制备N-[2-(8S)-1,6,7,8-四氢-2H-茚并[5,4-b]呋喃-8-基]丙酰胺，拉莫特龙的过程，其结构如下所示：（I）。
• [EN] PROCESS FOR THE PREPARATION OF AN INTERMEDIATE FOR RAMELTEON<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN PRODUIT INTERMÉDIAIRE DE RAMELTÉON
  申请人：RANBAXY LAB LTD

  公开号：WO2011027319A1

  公开（公告）日：2011-03-10

  The present invention relates to a process for the preparation of (2E)- 1,2,6,7- tetrahydro-8H-indeno[5,4-b]furan-8-ylideneethanenitrile of Formula (I). The present invention further relates to a process for the preparation of ramelteon using (2E)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylideneethanenitrile of Formula (I) as an intermediate.

  本发明涉及一种制备（2E）-1,2,6,7-四氢-8H-茚并[5,4-b]呋喃-8-基乙腈（化学式（I））的方法。本发明还涉及一种利用（2E）-1,2,6,7-四氢-8H-茚并[5,4-b]呋喃-8-基乙腈（化学式（I））作为中间体制备拉莫替昔的方法。