N-(1-diamantyl)acetamide | 30545-21-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(1-diamantyl)acetamide
• 英文别名: N-(diamantan-1-yl)acetamide；1-acetamidodiamantane；1-Acetamidodiadamantan；1-Acetamidodiamantan；medial-1-Acetamidodiamantan；N-(2-diamantyl)acetamide；1-acetaminodiamantane；N-(1-pentacyclo[7.3.1.14,12.02,7.06,11]tetradecanyl)acetamide
• CAS: 30545-21-2
• 化学式: C₁₆H₂₃NO
• 分子量: 245.365
• InChiKey: XADNPTMHMQGTJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  双金刚烷 、 乙腈 在 硝酸 、 溶剂黄146 作用下， 反应 2.0h， 以85%的产率得到N-(1-diamantyl)acetamide
  参考文献：
  名称：

  硝酸介质中二金刚烷衍生物的合成

  摘要：

  摘要 通过使金刚烷与硝酸或HNO 3 -AcOH混合物反应，然后添加含氮亲核试剂，可以合成1-单-和1,4-双官能金刚烷衍生物。由2-金刚烷-1-醇和硫氰酸甲酯在硫酸中合成了N-（二金刚烷-1-基）氨基甲磺酸甲酯。

  DOI：

  10.1134/s1070428021020081

文献信息

• Amidation of Diamantane with Organic Nitriles and CBr4 Under the Action of Granulated Zeolite FeHY
  作者：R. I. Khusnutdinov、N. А. Shchadneda、Yu. Yu. Mayakova、А. А. Yulamanova、А. N. Khazipova、B. I. Kutepov

  DOI：10.1134/s1070363218040084

  日期：2018.4

  N-(1- and 4-diamantyl)amides have been synthesized by the reaction of diamantane with organic nitriles in the presence of CBr4 under the action of granulated zeolite FeHY. The optimal ratios of the catalyst, reagents and the conditions for preparation of 1-N-diamantylamides in high yield have been found.

  在CBr 4的存在下，在粒状沸石FeHY的作用下，金刚烷与有机腈反应合成了N-（1-和4-二金刚烷基）酰胺。已经找到了高产率的催化剂，试剂的最佳比例和制备1- N-二酰胺基酰胺的条件。
• Amidation of Diamantane with Carboxylic Acid Amides and Carbon Tetrachloride in the Presence of Binder-Free Ni-HY Zeolite
  作者：R. I. Khusnutdinov、N. A. Shchadneva、Yu. Yu. Mayakova、G. Z. Kashfetdinova、A. N. Khazipova

  DOI：10.1134/s1070428020120106

  日期：2020.12

  Abstract N-(Diamantan-1- and 4-yl) carboxamides were synthesized by reaction of diamantane with carboxylic acid amides in the presence of carbon tetrachloride and binder-free Ni-HY zeolite. Optimal amounts of the reactants and catalyst and reaction conditions were found to obtain the target products in high yields.

  摘要 通过在四氯化碳和无粘结剂的Ni-HY沸石存在下，金刚烷与羧酸酰胺反应合成N-（Diamantan-1-和4-yl）羧酰胺。发现最适量的反应物和催化剂以及反应条件可以高产率获得目标产物。
• Method for Producing Substituted Diamantanes
  申请人：Schreiner Peter R.

  公开号：US20100036153A1

  公开（公告）日：2010-02-11

  The invention at hand provides at least dinitroxylated diamantanes. In addition, it provides methods for producing substituted diamantanes with high yields and selectivity. According to the invention, dinitroxylated diamantanes are suitable for being reacted with nucleophiles to form the corresponding disubstituted diamantanes. Surprisingly, it was discovered that at least dinitroxylated or hydroxylated diamantanes are rearranged in the presence of a strong acid, creating at least 4,9-nitroxylated or hydroxylated diamantanes. On the basis of this, 4,9-substituted diamantanes are able to be produced in a targeted manner by reaction with further nucleophiles. Thus, the invention at hand provides the following methods according to the present invention for producing at least disubstituted diamantanes: a) at least dinitroxylation, followed by the substitution of all nitroxy groups by a nucleophile or b) at least dinitroxylation, subsequent rearrangement in the presence of a strong acid, after realised rearrangement all nitroxy groups are replaced by a nucleophile or c) at least dinitroxylation, subsequent reaction with water (as nucleophile), rearrangement of the at least dihydroxylated compound in the presence of a strong acid, after realised rearrangement all hydroxy groups are replaced by another nucleophile.

  该发明提供至少二硝基化二莽烷。此外，它提供了一种高产率和选择性生产取代二莽烷的方法。根据该发明，二硝基化的二莽烷适合与亲核试剂反应，形成相应的二取代二莽烷。令人惊讶的是，在强酸存在的情况下发现，至少二硝基化或羟基化的二莽烷会重排，形成至少4,9-硝基化或羟基化的二莽烷。基于此，通过与进一步的亲核试剂反应，可以有针对性地生产4,9-取代的二莽烷。因此，该发明提供了以下根据本发明的方法，用于生产至少二取代的二莽烷：a) 至少二硝基化，然后用亲核试剂替换所有硝基团或b) 至少二硝基化，后在强酸存在下重排，重排后用亲核试剂替换所有硝基团或c) 至少二硝基化，后与水（作为亲核试剂）反应，在强酸存在下重排，重排后用另一亲核试剂替换所有羟基。
• Amidation of adamantane and diamantane with acetonitrile and bromotrichloromethane in the presence of Mo(CO)6 in aqueous medium
  作者：R. I. Khusnutdinov、N. A. Shchadneva、L. F. Khisamova、Yu. Yu. Mayakova、U. M. Dzhemilev

  DOI：10.1134/s1070428011120220

  日期：2011.12
• US8716539B2
  申请人：——

  公开号：US8716539B2

  公开（公告）日：2014-05-06