chroman-2-yl acetate | 23800-61-5

• 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: chroman-2-yl acetate
• 英文别名: (±)-chroman-2-yl acetate；2-acetoxy-chroman；Acetoxychromane；3,4-dihydro-2H-chromen-2-yl acetate
• CAS: 23800-61-5
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: ZQXQVNOKVIKPJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  chroman-2-yl acetate 在 Phenomenex Cellulose 4 作用下， 以 正己烷 、 异丙醇 为溶剂， 生成 (R)-chroman-2-yl acetate 、 [(2S)-3,4-dihydro-2H-chromen-2-yl] acetate
  参考文献：
  名称：

  Hydrolase-mediated resolution of the hemiacetal in 2-chromanols: The impact of remote substitution

  摘要：

  Hydrolase-catalysed dynamic kinetic resolutions of chroman-2-ol and 3-methyl chroman-2-ol can be effected with up to 88% conversion and 92% ee through the use of organic solvents. Extension to the resolution of the tolterodine precursor 1 proved more challenging. The presence of the remote phenyl substituent had a significant impact on the resolution and it was not possible to achieve high enantioselectivity together with efficient conversion from the focussed panel of enzymes screened. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2017.04.001
• 作为产物：
  描述：

  氢化肉桂酸内酯 在 吡啶 、 4-二甲氨基吡啶 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.5h， 生成 chroman-2-yl acetate
  参考文献：
  名称：

  Hydrolase-mediated resolution of the hemiacetal in 2-chromanols: The impact of remote substitution

  摘要：

  Hydrolase-catalysed dynamic kinetic resolutions of chroman-2-ol and 3-methyl chroman-2-ol can be effected with up to 88% conversion and 92% ee through the use of organic solvents. Extension to the resolution of the tolterodine precursor 1 proved more challenging. The presence of the remote phenyl substituent had a significant impact on the resolution and it was not possible to achieve high enantioselectivity together with efficient conversion from the focussed panel of enzymes screened. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2017.04.001

文献信息

• Methods for producing chiral chromones, chromanes, amino substituted chromanes and intermediates therefor
  申请人：——

  公开号：US20040053992A1

  公开（公告）日：2004-03-18

  Disclosed are process steps and novel processes for producing chromane compositions enriched in at least one (2R or 2S) enantiomer, preferably chroman-2-yl carboxylic acid compounds and chroman-2-yl carboxylic acid esters which are intermediates for producing platelet aggregation inhibitors and/or are themselves potent platelet aggregation inhibitors. Further disclosed are enzymatic processes for resolving chiral intermediates or final products to provide desired enantiomers.

  揭示了生产富含至少一种(2R或2S)对映体的香豆素组合物的工艺步骤和新型工艺，优选为香豆素-2-基羧酸化合物和香豆素-2-基羧酸酯，它们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。进一步揭示了用于解析手性中间体或最终产品以提供所需对映体的酶促过程。
• Asymmetric Catalysis via Cyclic, Aliphatic Oxocarbenium Ions
  作者：Sunggi Lee、Philip S. J. Kaib、Benjamin List

  DOI：10.1021/jacs.6b11993

  日期：2017.2.15

  A direct enantioselective synthesis of substituted oxygen heterocycles from lactol acetates and enolsilanes has been realized using a highly reactive and confined imidodiphosphorimidate (IDPi) catalyst. Various chiral oxygen heterocycles, including tetrahydrofurans, tetrahydropyrans, oxepanes, chromans, and dihydrobenzofurans, were obtained in excellent enantioselectivities by reacting the corresponding

  已经使用高反应性和受限的亚胺二磷亚胺酯 (IDPi) 催化剂实现了由乳醇乙酸酯和烯醇硅烷直接对映选择性合成取代氧杂环。各种手性氧杂环，包括四氢呋喃、四氢吡喃、氧杂环己烷、色满和二氢苯并呋喃，通过相应的内酯乙酸酯与多种烯醇硅烷反应以优异的对映选择性获得。机理研究表明，该反应通过与受限手性抗衡阴离子配对的不稳定、脂肪族、环状氧代碳鎓离子中间体进行。
• Methods for producing amino-substituted chromanes
  申请人：——

  公开号：US20040014804A1

  公开（公告）日：2004-01-22

  Disclosed are processes for producing benzopyran compounds, reduced 2-(chroman-2-yl) acetic acid compounds and 2-(6-aminochroman-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。
• 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。
• Chiral and achiral synthesis of 2-acyl substituted chromanes and their derivatives
  申请人：——

  公开号：US20040044225A1

  公开（公告）日：2004-03-04

  Disclosed are processes for producing a (2S) or (2R) 4-oxo-chroman-2-yl acyl compounds and chroman-2-yl acyl compounds, esters or amides thereof as well as derivatives thereof. Such processes may involve chiral synthesis or achiral synthesis, preferably coupled with a resolution procedure. Such compounds, particularly (2S) or (2R) acetic acid esters, are useful intermedates for producing platelet aggregation inhibitors and/or are themselves potent platelet aggregation inhibitors. Further disclosed are processes for making derivatives of such substantially pure, or enhanced compositions of single (2R) or (2S) enantiomer intermediates or processes for producing final products or salts from such desired enantiomers.

  本发明涉及制备（2S）或（2R）4-氧代-2-基香豆素酰基化合物和香豆素酰基化合物、酯或酰胺以及它们的衍生物的方法。这些方法可以涉及手性合成或非手性合成，优选与分离程序相结合。这些化合物，特别是（2S）或（2R）乙酸酯，可用作生产血小板聚集抑制剂的中间体，或者它们本身就是强效的血小板聚集抑制剂。本发明还涉及制备这些纯度高的单一（2R）或（2S）对映体中间体的衍生物的方法，或者从这些所需对映体制备最终产品或盐的方法。