ethyl rac-(6-amino-3,4-dihydro-2H-1-benzopyran-2-yl)acetate | 181074-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: ethyl rac-(6-amino-3,4-dihydro-2H-1-benzopyran-2-yl)acetate
• 英文别名: 6-amino-2[2H]-chromaneacetic acid ethyl ester；ethyl 2-(6-aminochroman-2-yl)acetate；ethyl [6-(amino)chroman-2-yl]acetate；ethyl (6-aminochroman-2-yl)-acetate；ethyl (6-aminochroman-2-yl)acetate；ethyl 2-(6-amino-3,4-dihydro-2H-chromen-2-yl)acetate
• CAS: 181074-34-0
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: FOBRYDDFZKXCFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  385.6±35.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl rac-(6-amino-3,4-dihydro-2H-1-benzopyran-2-yl)acetate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 ethyl 2-(6-aminochroman-2-yl)acetate hydrochloride
  参考文献：
  名称：

  Methods for producing amino-substituted chromanes

  摘要：

  本发明涉及生产苯并吡喃化合物、还原的2-(色满-2-基)乙酸化合物和2-(6-氨基色满-2-基)乙酸酯的过程，这些化合物是生产血小板聚集抑制剂的中间体和/或本身是有效的血小板聚集抑制剂。

  公开号：

  US20040014804A1
• 作为产物：
  描述：

  6-[[(1,1-dimethylethoxy)carbonyl]amino]-3,4-dihydro-2-oxo-2H-benzopyran 在 二异丁基氢化铝 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.5h， 生成 ethyl rac-(6-amino-3,4-dihydro-2H-1-benzopyran-2-yl)acetate
  参考文献：
  名称：

  Fused Bicyclic Gly-Asp β-Turn Mimics with Specific Affinity for GPIIb-IIIa

  摘要：

  Disubstituted isoquinolones 2 and 3 have affinity for GPIIb-IIIa and represent leads for further structural evaluation. Structure-activity studies centered on the bicyclic beta-turn mimic contained in these molecules indicated that this moiety could accommodate a variety of modifications. Specifically, monocyclic, 6,5-bicyclic, and 6,7-bicyclic structures provide compounds with affinity for GPIIb-IIIa. Within the 6,6-series, isoquinoline, tetralin, tetralone, and benzopyran nuclei yield potent antagonists that are specific for GPIIb-IIIa. Attachment of the arginine isostere (benzamidine) to the supporting nucleus can be accomplished with an ether or amide linkage, although the latter enhances activity. Several compounds in this series provided measurable blood levels after oral dosing. Conversion of the acid moiety in these molecules to an ester generally provided compounds which gave greater systemic exposure after oral administration. Absolute bioavailabilities in the rat for the ethyl ester prodrug derivatives of the tetralin, tetralone, and benzopyran analogues of 3 were 28%, 23%, and 24%, respectively.

  DOI：

  10.1021/jm990365y

文献信息

• Synthesis of 2-Acyl substituted chromanes and intermediates thereof
  申请人：——

  公开号：US20030233002A1

  公开（公告）日：2003-12-18

  Novel processes for producing enantiomerically enriched and enantiomerically pure compositions of 2-acyl substituted chromane compounds, and 2-acylchromane compounds that are intermediates for producing platelet aggregation inhibitors and/or are themselves potent platelet aggregation inhibitors are disclosed. Further disclosed are processes for producing salts such as acid addition salts for such enantiomerically enriched compositions.

  本发明揭示了用于生产富含对映体和对映纯2-酰基取代基色酮化合物的新工艺，以及用于生产血小板聚集抑制剂的中间体2-酰基色酮化合物和/或它们本身是有效的血小板聚集抑制剂的工艺。还揭示了用于生产酸盐等对这些富含对映体的成分的工艺。
• Glycoprotein IIb/IIIa antagonists
  申请人：Eli Lilly and Company

  公开号：US05731324A1

  公开（公告）日：1998-03-24

  This invention relates to certain bicyclic compounds having a nucleus formed of two fused six membered rings, for example, benzopyran, isoquinoline, isoquinolone, tetrahydronaphthalene, dihydronaphthalene, or tetralone, substituted with both basic and acidic functionality, which are useful in inhibition of platelet aggregation.

  该发明涉及具有由两个融合的六元环组成的核的某些双环化合物，例如苯并吡喃、异喹啉、异喹酮、四氢萘、二氢萘或四酮，这些化合物被取代为既具有碱性功能又具有酸性功能，对抑制血小板聚集具有用处。
• Methods for producing amino substituted chromanes and intermediates therefor
  申请人：Scarborough Robert

  公开号：US20050004377A1

  公开（公告）日：2005-01-06

  Disclosed are process steps and processes for producing chromane compounds, preferably 2-(6-amino-chroman-2yl) acetic acid esters which are intermediates for producing platelet aggregation inhibitors and/or are themselves potent platelet aggregation inhibitors.

  公开了生产色苷化合物的过程步骤和工艺，优选为生产血小板聚集抑制剂的中间体或本身是有效的血小板聚集抑制剂的2-(6-氨基色苷基)乙酸酯。
• Method for resolving chiral (2s) and (2r) chromanes
  申请人：——

  公开号：US20040014994A1

  公开（公告）日：2004-01-22

  Disclosed are processes for resolving chiral (2S) and (2R) benzopyrans, racemizing benzopyrans, and recycling racemized benzopyrans to increase yield of a desired enantiomer to provide purified or substantially purified bicyclic amino substituted benzopyran derivatives. Such benzopyran derivatives are preferably chromans which can be coupled with benzoyl derivatives via an amide bond to produce potent platelet aggregation inhibitors.

  公开了用于解决手性（2S）和（2R）苯并吡喃、使苯并吡喃消旋以及回收消旋苯并吡喃的方法，以提高所需对映体的产量，从而提供纯化或基本纯化的双环氨基取代苯并吡喃衍生物。这些苯并吡喃衍生物最好是色苷，可以通过酰苯衍生物通过酰胺键耦合，生产出强效的血小板聚集抑制剂。
• Methods for producing amino substituted chromanes and intermediates thereof
  申请人：——

  公开号：US20040225137A1

  公开（公告）日：2004-11-11

  Disclosed are processes for producing chromane compounds, preferably chroman-2-yl acetic acid compounds and 6-amino-chroman-2-yl acetic acid esters which are intermediates for producing platelet aggregation inhibitors and/or are themselves potent platelet aggregation inhibitors.

  本发明涉及生产色烷化合物的方法，优选生产色烷-2-乙酸化合物和6-氨基色烷-2-乙酸酯，它们是生产血小板聚集抑制剂的中间体和/或本身具有强效的血小板聚集抑制剂。