6,8-difluoro-2H-chromene-3-carbonitrile | 1043421-43-7

• 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: 6,8-difluoro-2H-chromene-3-carbonitrile
• CAS: 1043421-43-7
• 化学式: C₁₀H₅F₂NO
• 分子量: 193.153
• InChiKey: IUSDGKMRLNYAAA-UHFFFAOYSA-N

物化性质

• 沸点：
  301.0±42.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,8-difluoro-2H-chromene-3-carbonitrile 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以95%的产率得到6,8-difluoro-2H-chromene-3-carboxamide
  参考文献：
  名称：

  Process Research for Multikilogram Production of Etamicastat: A Novel Dopamine β-Hydroxylase Inhibitor

  摘要：

  In order to develop a manufacturing route to etamicastat, three synthetic approaches to the pivotal chiral 3-aminochroman intermediate have been studied as well as four methods for the construction of the 2-aminoethyl imidazolethione fragment. The evolution of the synthetic strategy based on the early discovery route was described. By focusing on the use of readily available starting materials it was possible to avoid chromatography steps and expensive reagents, bringing about significant improvements in cost and throughput. The best route involves construction of the chiral centre by asymmetric hydrogenation.

  DOI：

  10.1021/op300012d
• 作为产物：
  描述：

  2,4-二氟苯酚 在 三乙烯二胺 、 乌洛托品 作用下， 反应 34.0h， 生成 6,8-difluoro-2H-chromene-3-carbonitrile
  参考文献：
  名称：

  Process Research for Multikilogram Production of Etamicastat: A Novel Dopamine β-Hydroxylase Inhibitor

  摘要：

  In order to develop a manufacturing route to etamicastat, three synthetic approaches to the pivotal chiral 3-aminochroman intermediate have been studied as well as four methods for the construction of the 2-aminoethyl imidazolethione fragment. The evolution of the synthetic strategy based on the early discovery route was described. By focusing on the use of readily available starting materials it was possible to avoid chromatography steps and expensive reagents, bringing about significant improvements in cost and throughput. The best route involves construction of the chiral centre by asymmetric hydrogenation.

  DOI：

  10.1021/op300012d

文献信息

• [EN] PROCESSES FOR PREPARING MEDICAMENTS FOR THE TREATMENT OF CARDIOVASCULAR DISEASES AND INTERMEDIATES FOR USE THEREIN<br/>[FR] PROCÉDÉS DE PRÉPARATION DE MÉDICAMENTS POUR LE TRAITEMENT DE MALADIES CARDIOVASCULAIRES ET INTERMÉDIAIRES PRÉVUS À CET EFFET
  申请人：BIAL PORTELA & CA SA

  公开号：WO2015038022A1

  公开（公告）日：2015-03-19

  The present invention provides a compound of formula N wherein: X is CH2, oxygen or sulphur; R1, R2 and R3 are the same or different and signify hydrogens, halogens, alkyl, alkyloxy, hydroxy, nitro, alkylcarbonylamino, alkylamino or dialkylamino group, wherein N is in the form of the individual R- and S-enantiomer or a mixture of the (R)- and (S)-enantiomer. The present invention also provides a compound of formula MA. The present invention also provides processes for preparing the above compounds, and processes involving their use. The compounds are particularly useful as intermediates in the synthesis of peripherally-selective inhibitors of dopamine-ß-hydroxylase.

  本发明提供了一个公式为N的化合物，其中：X为CH2、氧或硫；R1、R2和R3相同或不同，表示氢、卤素、烷基、烷氧基、羟基、硝基、烷基羰基氨基、烷基氨基或二烷基氨基基团，其中N以单一的R-和S-对映体形式存在，或者是(R)-和(S)-对映体的混合物。本发明还提供了一个公式为MA的化合物。本发明还提供了制备上述化合物的方法，以及涉及它们使用的方法。这些化合物在外周选择性多巴胺-ß-羟化酶抑制剂的合成中特别有用。
• Chroman Compounds
  申请人：Taugerbeck Andreas

  公开号：US20100102274A1

  公开（公告）日：2010-04-29

  The chroman compounds of the formula I according to the invention R 1 -(A 1 -Z 1 ) a —W 1 —(Z 2 -A 2 ) b -Z 3 —W 2 —(Z 4 -A 3 ) n -R 2 in which R 1 , A 1 , A 2 , A 3 , W 1 , W 2 , Z 1 , Z 2 , Z 3 , Z 4 , a, b and c have the meanings indicated in claim 1 , have two moieties W 1 and W 2 derived from chroman. The compounds are suitable as components of anisotropic switching media, as used, for example, in liquid-crystal display devices.

  根据本发明的公式I中的铬曼化合物，其化学结构为R1-(A1-Z1)a—W1—(Z2-A2)b-Z3—W2—(Z4-A3)n-R2，其中R1、A1、A2、A3、W1、W2、Z1、Z2、Z3、Z4、a、b和c的含义如权利要求书中所示，具有两个源自铬曼的分子W1和W2。这些化合物适用于各种各样的各向异性开关介质，例如液晶显示器件的组成部分。
• Chroman compounds
  申请人：Merck Patent Gesellschaft

  公开号：US07955664B2

  公开（公告）日：2011-06-07

  The chroman compounds of the formula I according to the invention R1-(A1-Z1)a—W1—(Z2-A2)b-Z3—W2—(Z4-A3)c-R2 in which R1, A1, A2, A3, W1, W2, Z1, Z2, Z3, Z4, a, b and c have the meanings indicated in claim 1, have two moieties W1 and W2 derived from chroman. The compounds are suitable as components of anisotropic switching media, as used, for example, in liquid-crystal display devices.

  本发明的公式I中的铬曼化合物为R1-(A1-Z1)a—W1—(Z2-A2)b-Z3—W2—(Z4-A3)c-R2，在该式中，R1、A1、A2、A3、W1、W2、Z1、Z2、Z3、Z4、a、b和c的含义如权利要求书1所示，其中含有两个源自铬曼的分子W1和W2。这些化合物适用于各向异性开关介质的组成部分，例如在液晶显示器件中使用。
• Processes for Preparing Medicaments for the Treatment of Cardiovascular Diseases and Intermediates for Use Therein
  申请人：Bial - Portela & CA., S.A.

  公开号：US20160221981A1

  公开（公告）日：2016-08-04

  The present invention provides a compound of formula N wherein: X is CH 2 , oxygen or sulphur; R 1 , R 2 and R 3 are the same or different and signify hydrogens, halogens, alkyl, alkyloxy, hydroxy, nitro, alkylcarbonylamino, alkylamino or dialkylamino group, wherein N is in the form of the individual R- and S-enantiomer or a mixture of the (R)- and (S)-enantiomer. The present invention also provides a compound of formula MA. The present invention also provides processes for preparing the above compounds, and processes involving their use. The compounds are particularly useful as intermediates in the synthesis of peripherally-selective inhibitors of dopamine-β-hydroxylase.

  本发明提供了一个化合物的公式N，其中：X是CH2，氧或硫；R1、R2和R3相同或不同，表示氢、卤素、烷基、烷氧基、羟基、硝基、烷基羰基氨基、烷基氨基或二烷基氨基基团，其中N以单个R-和S-对映体或(R)-和(S)-对映体的混合物形式存在。本发明还提供了一个化合物的公式MA。本发明还提供了制备上述化合物的方法以及涉及它们使用的方法。这些化合物在外周选择性多巴胺-β-羟化酶抑制剂的合成中特别有用。
• Process for the Preparation of 2H-Chromene-3-Carbamate Derivatives
  申请人：Broadbelt Brian

  公开号：US20100298580A1

  公开（公告）日：2010-11-25

  Compounds of formula I, V, VI and II, and processes for their preparation, wherein R 1 , R 2 and R 3 are the same or different and signify hydrogens, halogens, alkyl, alkyloxy, hydroxy, nitro, alkylcarbonylamino, alkylamino or dialkylamino group; and R 4 is alkyl or aryl. There is also provided a process for preparing a compound of formula B from the compounds of formula V and I.

  公式I、V、VI和II的化合物及其制备方法，其中R1、R2和R3相同或不同，表示氢、卤素、烷基、烷氧基、羟基、硝基、烷基羰基氨基、烷基氨基或二烷基氨基基团; 而R4是烷基或芳基。还提供了一种从公式V和I的化合物制备公式B化合物的方法。