(R)-N-(1-(naphthalen-1-yl)ethyl)-N-(3-(3-(trifluoromethyl)phenyl)propyl)formamide | 1601479-86-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-N-(1-(naphthalen-1-yl)ethyl)-N-(3-(3-(trifluoromethyl)phenyl)propyl)formamide
• 英文别名: N-[(1R)-1-naphthalen-1-ylethyl]-N-[3-[3-(trifluoromethyl)phenyl]propyl]formamide
• CAS: 1601479-86-0
• 化学式: C₂₃H₂₂F₃NO
• 分子量: 385.429
• InChiKey: BNDNPFUGZRHKJN-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-N-(1-(naphthalen-1-yl)ethyl)-N-(3-(3-(trifluoromethyl)phenyl)propyl)formamide 在 盐酸 作用下， 以 水 为溶剂， 反应 12.0h， 以100%的产率得到盐酸甲状旁腺激素
  参考文献：
  名称：

  Construction of 3-arylpropylamines using Heck arylations. The total synthesis of cinacalcet hydrochloride, alverine, and tolpropamine

  摘要：

  New synthetic routes toward the commercial drugs cinacalcet hydrochloride, alverine, and tolpropamine were developed using a Heck-Matsuda arylation as the key-step. Several reaction conditions were evaluated for the Heck-Matsuda reaction using allylamine derivatives and arenediazonium salts. For cinacalcet hydrochloride, N-formylamide provided the best result, furnishing the synthetic target in a very high overall yield (75% over five steps). For alverine, the best results were obtained using a double Heck-Matsuda strategy, providing alverine in an excellent overall yield (69%) from N-acetyl diallylamine in three steps. Tolpropamine was synthesized in a 46% yield over five steps using an efficient reductive Heck-Matsuda arylation between p-bromo-methylcinnamate with 3-chloro tolyldiazonium salt, generating the beta,beta-diaryl propionate that was converted to tolpropamine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.014
• 作为产物：
  描述：

  (R)-N-allyl-N-(1-(naphthalen-1-yl)ethyl)formamide 在 tris-(dibenzylideneacetone)dipalladium(0) 、 氢气 、 sodium acetate 作用下， 以 苯甲腈 为溶剂， 反应 13.0h， 生成 (R)-N-(1-(naphthalen-1-yl)ethyl)-N-(3-(3-(trifluoromethyl)phenyl)propyl)formamide
  参考文献：
  名称：

  Construction of 3-arylpropylamines using Heck arylations. The total synthesis of cinacalcet hydrochloride, alverine, and tolpropamine

  摘要：

  New synthetic routes toward the commercial drugs cinacalcet hydrochloride, alverine, and tolpropamine were developed using a Heck-Matsuda arylation as the key-step. Several reaction conditions were evaluated for the Heck-Matsuda reaction using allylamine derivatives and arenediazonium salts. For cinacalcet hydrochloride, N-formylamide provided the best result, furnishing the synthetic target in a very high overall yield (75% over five steps). For alverine, the best results were obtained using a double Heck-Matsuda strategy, providing alverine in an excellent overall yield (69%) from N-acetyl diallylamine in three steps. Tolpropamine was synthesized in a 46% yield over five steps using an efficient reductive Heck-Matsuda arylation between p-bromo-methylcinnamate with 3-chloro tolyldiazonium salt, generating the beta,beta-diaryl propionate that was converted to tolpropamine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.014

文献信息

• Carbon Dioxide Based N-Formylation of Amines Catalyzed by Fluoride and Hydroxide Anions
  作者：Martin Hulla、Felix D. Bobbink、Shoubhik Das、Paul J. Dyson

  DOI：10.1002/cctc.201601027

  日期：2016.11.8

  We described herein a simple approach for N‐formylation with CO2 and hydrosilane reducing agents. Fluoride and hydroxide salts efficiently catalyzed the reaction, principally through activation of the hydrosilanes, which led to hydrosilane reactivities comparable to those of NaBH4/LiAlH4. Consequently, the N‐formylation of amines with CO2 could be achieved at room temperature and atmospheric pressure

  我们在这里描述了一种简单的方法，用于用CO 2和氢硅烷还原剂进行N-甲酰化。氟化物和氢氧化物盐有效地催化了反应，主要是通过氢化硅烷的活化，这导致了与NaBH 4 / LiAlH 4相当的氢化硅烷反应性。因此，可以在室温和大气压下实现胺与CO 2的N-甲酰化。这些阴离子催化剂的机理与当前报道的体系形成了鲜明的对比，对于该体系，CO 2的活化是关键的机械步骤。使用四丁基氟化铵作为简单的铵盐催化剂，可以以高收率和高选择性获得脂族和芳族胺的N-甲酰化产物。
• Iron‐Catalyzed Selective <i>N</i> ‐Methylation and <i>N</i> ‐Formylation of Amines with CO ₂
  作者：Wen‐Duo Li、Dao‐Yong Zhu、Gang Li、Jie Chen、Ji‐Bao Xia

  DOI：10.1002/adsc.201900906

  日期：2019.11.19

  We herein describe an efficient iron‐catalyzed selective N‐methylation and N‐formylation of amines with CO2 and silane using mono‐phosphine as ligand. With commercially available [CpFe(CO)2]2 as catalyst, Fe‐catalyzed methylation of amines was achieved with triphenylphosphine as a ligand. Using tributylphosphine as a ligand, Fe‐catalyzed formylation of amines was realized at a lower temperature. The

  我们在此描述了使用单膦作为配体的一种有效的铁催化的胺与CO 2和硅烷的选择性N-甲基化和N-甲酰化反应。使用可商购的[CpFe（CO）2 ] 2作为催化剂，用三苯基膦作为配体实现了铁催化的胺甲基化。使用三丁基膦作为配体，可以在较低温度下实现铁催化的胺甲酰化反应。该方法已成功应用于含有胺部分的药物分子的晚期甲基化和甲酰化。
• Construction of 3-arylpropylamines using Heck arylations. The total synthesis of cinacalcet hydrochloride, alverine, and tolpropamine
  作者：Patrícia Prediger、Allan Ribeiro da Silva、Carlos Roque Duarte Correia

  DOI：10.1016/j.tet.2013.10.014

  日期：2014.5

  New synthetic routes toward the commercial drugs cinacalcet hydrochloride, alverine, and tolpropamine were developed using a Heck-Matsuda arylation as the key-step. Several reaction conditions were evaluated for the Heck-Matsuda reaction using allylamine derivatives and arenediazonium salts. For cinacalcet hydrochloride, N-formylamide provided the best result, furnishing the synthetic target in a very high overall yield (75% over five steps). For alverine, the best results were obtained using a double Heck-Matsuda strategy, providing alverine in an excellent overall yield (69%) from N-acetyl diallylamine in three steps. Tolpropamine was synthesized in a 46% yield over five steps using an efficient reductive Heck-Matsuda arylation between p-bromo-methylcinnamate with 3-chloro tolyldiazonium salt, generating the beta,beta-diaryl propionate that was converted to tolpropamine. (C) 2013 Elsevier Ltd. All rights reserved.