(4-羟基-6-氧代四氢-2H-吡喃-2-基)乙腈 | 791115-49-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: (4-羟基-6-氧代四氢-2H-吡喃-2-基)乙腈
• 英文名称: 6-cyano-methyl-4-hydroxy-tetrahydropyran-2-one
• 英文别名: (4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-acetonitrile；2-(4-Hydroxy-6-oxooxan-2-yl)acetonitrile
• CAS: 791115-49-6
• 化学式: C₇H₉NO₃
• 分子量: 155.153
• InChiKey: NUTZEIABCUGDLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-羟基-6-氧代四氢-2H-吡喃-2-基)乙腈 、 原甲酸三乙酯 、 1,4-环己二酮 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以82%的产率得到
  参考文献：
  名称：

  一种他汀类药物中间体及其制备方法和应用

  摘要：

  本发明公开一种可作为他汀类药物中间体的具有如通式I所示结构的化合物及其制备方法和应用。通过引入环己二酮，本发明可经一步反应生成双分子中间体，可以实现利用价廉易得的原料、高收率且环境友好的制备他汀类药物中间体的目的，更适合工业化生产的进行。

  公开号：

  CN104447784B

文献信息

• [EN] PROCESS FOT THE PREPARATION OF (4-HYDROXY-6-OXO-TETRAHYDROPYRAN-2-YL) ACETONITRILE AND DERIVATIVES THEREOF<br/>[FR] PROCEDE DE PREPARATION DE (4-HYDROXY-6-OXO-TETRAHYDROPYRAN-2-YL)-ACETONITRILE ET DE DERIVES CORRESPONDANTS
  申请人：DSM IP ASSETS BV

  公开号：WO2004096788A1

  公开（公告）日：2004-11-11

  The invention relates to a process for the preparation of (4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-acetonitrile from 6-X-substituted-methyl-4-hydroxy-tetrahydro-pyran-2-one, wherein X stands for a leaving group, by reacting 6-X-substituted-methyl-4-hydroxy-tetrahydro-pyran-2-one with a cyanide ion in water and by subsequent lowering of the pH to a pH between 0 and 5. (4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-acetonitrile and other compounds obtainable from (4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-acetonitrile may suitably be used in the preparation of a pharmaceutical preparation, more in particular in the preparation of statins, more in particular in the preparation of Atorvastatine or a salt thereof, for instance its calcium salt. The invention also relates to (4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-acetonitrile and other compounds obtainable therefrom.

  该发明涉及一种从6-X-取代-甲基-4-羟基-四氢吡喃-2-酮制备(4-羟基-6-氧代-四氢吡喃-2-基)-乙腈的方法，其中X代表一个离去基团，通过在水中将6-X-取代-甲基-4-羟基-四氢吡喃-2-酮与氰离子反应，然后将pH降低至0至5之间的pH。从(4-羟基-6-氧代-四氢吡喃-2-基)-乙腈获得的化合物和其他化合物可适用于制备药物制剂，更具体地用于制备他汀类药物，更具体地用于制备阿托伐他汀或其盐，例如其钙盐。该发明还涉及(4-羟基-6-氧代-四氢吡喃-2-基)-乙腈和可从中获得的其他化合物。
• PROCESS FOR THE PREPARATION OF (4-HYDROXY-6-OXO-TETRAHYDROPYRAN-2-YL) ACETONITRILE AND DERIVATIVES THEREOF
  申请人：DSM IP Assets B.V.

  公开号：EP1620423B1

  公开（公告）日：2008-02-20
• Process for the preparation of (4-hydroxy-6-oxo-tetrahydropyran-2-yl) acetonitrile and derivatives
  申请人：Mink Daniel

  公开号：US20060258733A1

  公开（公告）日：2006-11-16

  The invention relates to a process for the preparation of (4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-acetonitrile from 6-X-substituted-methyl-4-hydroxy-tetrahydro-pyran-2-one, wherein X stands for a leaving group, by reacting 6-X-substituted-methyl-4-hydroxy-tetrahydro-pyran-2-one with a cyanide ion in water and by subsequent lowering of the pH to a pH between 0 and 5. (4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-acetonitrile and other compounds obtainable from (4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-acetonitrile may suitably be used in the preparation of a pharmaceutical preparation, more in particular in the preparation of statins, more in particular in the preparation of Atorvastatine or a salt thereof, for instance its calcium salt. The invention also relates to (4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-acetonitrile and other compounds obtainable therefrom.
• US7423162B2
  申请人：——

  公开号：US7423162B2

  公开（公告）日：2008-09-09
• [EN] PROCESS FOR THE PREPARATION OF EPOXIDE INTERMEDIATES FOR PHARMACEUTICAL COMPOUNDS SUCH AS STATINS<br/>[FR] PROCÉDÉ DE PRÉPARATION D'INTERMÉDIAIRES ÉPOXIDÉS POUR DES COMPOSÉS PHARMACEUTIQUES TELS QUE DES STATINES
  申请人：DSM IP ASSETS BV

  公开号：WO2007137816A1

  公开（公告）日：2007-12-06

  [EN] The invention relates to a process for the preparation of intermediates, which can suitably be used in the preparation of active pharmaceutical ingredients, in particular in the preparation of HMG-CoA reductase inhibitors, more in particular in the preparation of statines, for example lovastatin, cerivastatin, rosuvastatin, simvastatin, pravastatin, atorvastatin or fluvastatin, most in particular of atorvastatin. The intermediates are prepared according to the process of the invention by reaction of (enantiomerically enriched) 6-chloromethyl-4-hydroxy-tetrahydro-pyran- 2-one or the ring opened formed thereof with cyanide in the presence of a haloalcohol dehalogenase, preferably HheA from Arthrobacter sp. strain AD2.
  [FR] La présente invention concerne un procédé de préparation d'intermédiaires qui peuvent être utilisés de manière appropriée dans la préparation de matières actives pharmaceutiques, en particulier dans la préparation d'inhibiteurs de la HMG-CoA réductase et tout particulièrement dans la préparation de statines, par exemple la lovastatine, la cérivastatine, la rosuvastatine, la simvastatine, la pravastatine, l'atorvastatine ou la fluvastatine, tout particulièrement l'atorvastatine. Selon le procédé de l'invention, les intermédiaires sont préparés par une réaction entre la 6-chlorométhyl-4-hydroxy-tétrahydro-pyran-2-one (enrichie sur le plan des énantiomères), ou le cycle ouvert formé à partir de ce composé, et du cyanure en présence d'une haloalcool-déshalogénase, de préférence la HheA de la souche AD2 d'une Arthrobacter sp.