2-(1-羟基-7-甲氧基-1,2,3,4-四氢-萘-1-基)-乙腈 | 59081-65-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 2-(1-羟基-7-甲氧基-1,2,3,4-四氢-萘-1-基)-乙腈
• 英文名称: 2-(1-hydroxyl-7-methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetonitrile
• 英文别名: 1-hydroxy-7-methoxy-1,2,3,4-tetrahydro-1-naphthylacetonitrile；2-(1-hydroxyl-7-methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetcnitrile；2-(1-hydroxy-7-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetonitrile；2-(1-hydroxy-7-methoxy-3,4-dihydro-2H-naphthalen-1-yl)acetonitrile
• CAS: 59081-65-1
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: WEYNDQBNPRNRPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-羟基-7-甲氧基-1,2,3,4-四氢-萘-1-基)-乙腈 在 Raney-Ni 氢气 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 30.0~40.0 ℃ 、1.1 MPa 条件下， 反应 5.0h， 生成 阿戈美拉汀
  参考文献：
  名称：

  [EN] AGOMELATINE INTERMEDIATES AND PREPARATION METHOD THEREOF
  [FR] INTERMÉDIAIRES D'AGOMÉLATINE ET LEUR PROCÉDÉ DE PRÉPARATION

  摘要：

  本发明提供了用于制备阿戈美拉汀的中间化合物及其制备方法。同时，还提供了两种新型中间体化合物。该方法操作简单、控制良好、适用于工业生产，且具有高纯度，无需繁琐的操作如精馏和柱层析分离。同时，这两种新中间体的制备方法简单且收率高。

  公开号：

  WO2011153939A1
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 、 乙腈 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以95%的产率得到2-(1-羟基-7-甲氧基-1,2,3,4-四氢-萘-1-基)-乙腈
  参考文献：
  名称：

  萘系褪黑素受体配体的合成

  摘要：

  描述了一种高效且通用的合成方法，用于合成褪黑激素、化合物 7 及其 2-烷基取代类似物 8 的萘类似物。该方法的特点是通过将 LiCH2CN 亲核加成到取代的 1-四氢萘酮，然后通过 2 步反应序列进行芳构化、用 DDQ 脱氢和 TsOH 催化脱水来合成取代的 1-萘基乙腈 12 和 19。

  DOI：

  10.1081/scc-100000591

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF AGOMELATINE USING NOVEL INTERMEDIATES<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION D'AGOMÉLATINE À L'AIDE DE NOUVEAUX INTERMÉDIAIRES
  申请人：SYMED LABS LTD

  公开号：WO2014064706A1

  公开（公告）日：2014-05-01

  Provided herein are novel, commercially viable and industrially advantageous processes for the preparation of Agomelatine or a salt thereof, in high yield and purity, using novel intermediates.

  本文提供了一种新颖、商业可行且在工业上具有优势的过程，用于制备阿戈美拉汀或其盐，高产率和纯度，使用新颖的中间体。
• Process for the preparation of agomelatine
  申请人：Procos S.p.A.

  公开号：EP2703383A1

  公开（公告）日：2014-03-05

  Disclosed is a process for the synthesis of Agomelatine (1), N-(2-(7-methoxynaphthalen-1-yl)ethyl)acetamide from ethyl 2-(7-methoxynaphthalen-1-yl)acetate (4). Said synthesis method is particularly advantageous compared with known procedures because it uses low-cost reagents under mild reaction conditions and allows the isolation of a product with excellent yields and quality.

  本发明公开了一种合成Agomelatine（1），即N-（2-（7-甲氧基萘-1-基）乙基）乙酰胺的方法，该方法从乙酸2-（7-甲氧基萘-1-基）乙酯（4）开始。该合成方法与已知的方法相比具有特别的优势，因为它使用低成本试剂在温和反应条件下，可以得到产量和质量均优异的产物。
• AGOMELATINE INTERMEDIATES AND PREPARATION METHOD THEREOF
  申请人：Zhang Peng

  公开号：US20130267738A1

  公开（公告）日：2013-10-10

  The present invention relates to the intermediate compounds for preparation of agomelatine, as well as the preparation methods thereof. The intermediate of the present invention for preparation of agomelatine is compound A as shown in the following formula. Also provided are two novel intermediate compounds. When we use these new intermediate compounds to prepare agomelatine, it is simple to manipulate, well-controlled and with high purity, without complicated operations such as rectification and column chromatography separation, and suitable for industrial production. Meanwhile, the preparation methods of the two new intermediates themselves is simple and high yield, only using the most commonly-used 7-methoxy-tetralone as original starting material and undergoing one step of reaction to obtain the intermediates, followed by one more step of converting the intermediate compounds to desired product agomelatine. Said reaction processes are greatly simplified, with the reaction yield being improved and the difficulty in purification of previous method being overcome, as compare with the previous technique for preparation of agomelatine. Typically, the yield of the present invention is over 70%.

  本发明涉及用于制备阿戈美拉汀的中间化合物及其制备方法。本发明用于制备阿戈美拉汀的中间体是以下式子中的化合物A。同时提供了两种新的中间化合物。当我们使用这些新的中间化合物来制备阿戈美拉汀时，操作简单、控制良好、纯度高，无需如精馏和柱层析分离等复杂操作，适合工业生产。同时，这两种新中间体本身的制备方法简单且产率高，只需使用最常用的7-甲氧基四氢萘作为原始起始材料，经过一步反应即可获得中间体，然后再进行一步将中间体化合物转化为所需的产品阿戈美拉汀。与以往制备阿戈美拉汀的技术相比，本发明的反应过程大大简化，反应产率提高，克服了以往方法中净化困难的问题。通常情况下，本发明的产率超过70%。
• Agomelatine intermediates and preparation method thereof
  申请人：Zhang Peng

  公开号：US08779199B2

  公开（公告）日：2014-07-15

  The present invention relates to the intermediate compounds for preparation of agomelatine, as well as the preparation methods thereof The intermediate of the present invention for preparation of agomelatine is compound A as shown in the following formula. Also provided are two novel intermediate compounds. When we use these new intermediate compounds to prepare agomelatine, it is simple to manipulate, well-controlled and with high purity, without complicated operations such as rectification and column chromatography separation, and suitable for industrial production. Meanwhile, the preparation methods of the two new intermediates themselves is simple and high yield, only using the most commonly-used 7-methoxy-tetralone as original starting material and undergoing one step of reaction to obtain the intermediates, followed by one more step of converting the intermediate compounds to desired product agomelatine. Said reaction processes are greatly simplified, with the reaction yield being improved and the difficulty in purification of previous method being overcome, as compare with the previous technique for preparation of agomelatine. Typically, the yield of the present invention is over 70%.

  本发明涉及用于制备阿戈美拉汀的中间化合物及其制备方法。本发明用于制备阿戈美拉汀的中间体是以下式子中所示的化合物A。同时提供了两种新型中间化合物。当使用这些新型中间化合物制备阿戈美拉汀时，操作简单、易于控制、纯度高，无需繁琐的操作如精馏和柱层析分离，适用于工业生产。同时，这两种新型中间体的制备方法简单且高产，只需使用最常用的7-甲氧基四氢萘酮作为原始起始材料，经过一步反应即可得到中间体，再经过一步将中间化合物转化为所需产品阿戈美拉汀。与以前制备阿戈美拉汀的技术相比，本发明的反应过程大大简化，反应产率提高，克服了以前方法中净化困难的问题。通常，本发明的产率超过70%。
• [EN] PROCESS FOR PREPARATION OF N-[2-(7-METHOXY-1-NAPHTITYL)ETHYL] ACETAMIDE AND ITS NOVEL CRYSTALLINE FORMS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE N-[2- (7-MÉTHOXY-L-NAPHTHYL) ÉTHYL] ACÉTAMIDE ET SES NOUVELLES FORMES CRISTALLINES
  申请人：MSN LAB LTD

  公开号：WO2012046253A3

  公开（公告）日：2012-05-31