(+/-)-N-(2-exo-bicyclo<2.2.1>heptyl)acetamide | 1485-59-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+/-)-N-(2-exo-bicyclo<2.2.1>heptyl)acetamide
• 英文别名: 2-exo-acetamidobicyclo<2.2.1>-heptane；N-bicyclo[2.2.1]hept-2-yl-acetamide；N-(exo-2-norbornyl)acetamide；exo-2-acetylaaminonorbornane；exo-2-acetylaminonorbornane；exo-N-norbornylacetamide；N-[(1R,2R,4S)-Bicyclo[2.2.1]heptan-2-yl]acetamide；N-[(1R,2R,4S)-2-bicyclo[2.2.1]heptanyl]acetamide
• CAS: 1485-59-2；28607-02-5；56895-94-4；67815-08-1；67844-28-4
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: QURAXMRQNAFYID-DJLDLDEBSA-N

物化性质

• 熔点：
  139-140 °C
• 沸点：
  313.7±9.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-N-(2-exo-bicyclo<2.2.1>heptyl)acetamide 在 水 作用下， 反应 30.0h， 以138 kg的产率得到(1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamine
  参考文献：
  名称：

  Comparison of Large-Scale Routes to Manufacture Chiral exo-2-Norbornyl Thiourea

  摘要：

  Two routes aimed at the manufacture of chiral exo-2-norbornyl thiourea (1) on large scale are described. The first approach involves live chemical steps and hinges on a classical resolution via diastereomeric salt formation. The synthesis utilizes amine 2 as the resolution handle. The second approach includes two chemical steps and a chiral chromatography of (+/-)-1. Despite the larger initial investment necessary to acquire the chiral stationary phase used in the chromatographic approach, the shorter reaction sequence and efficiency of the chromatographic separation make the second route a more attractive option tor long-term applications.

  DOI：

  10.1021/op9002328
• 作为产物：
  描述：

  降莰烷 在 ferrous perchlorate 、 双氧水 、 乙腈 作用下， 生成 (+/-)-N-(2-exo-bicyclo<2.2.1>heptyl)acetamide
  参考文献：
  名称：

  Kotani, Eiichi; Kobayashi. Shigeki; Ishii, Yoko, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 11, p. 4671 - 4679

  摘要：

  DOI：

文献信息

• Radical Transfer Hydroamination with Aminated Cyclohexadienes Using Polarity Reversal Catalysis:  Scope and Limitations
  作者：Joyram Guin、Christian Mück-Lichtenfeld、Stefan Grimme、Armido Studer

  DOI：10.1021/ja0692581

  日期：2007.4.1

  The synthesis of various new 1-aminated-2,5-cyclohexadienes is described. These reagents can be used in radical transfer hydroaminations of unactivated and electron-rich double bonds. With thiols as polarity reversal catalysts good yields are obtained. The radical hydroamination occurs with good to excellent anti-Markovnikov selectivity. Many functional groups such as alcohols, silyl ethers, phosphonates

  描述了各种新的 1-胺化-2,5-环己二烯的合成。这些试剂可用于未活化和富电子双键的自由基转移加氢胺化。使用硫醇作为极性反转催化剂可获得良好的产率。自由基加氢胺化以良好至极好的抗马尔可夫尼科夫选择性发生。许多官能团如醇、甲硅烷基醚、膦酸酯、芳基溴化物、酰亚胺、酰胺以及酸性质子在反应条件下是可以耐受的。DFT 计算提供了对甲硅烷基、烷基和氨基取代的环己二烯基的芳构化以生成相应的 C-、Si-和 N-中心自由基的见解。
• Amidation of norbornene with organic nitriles in the presence of water catalyzed by iron compounds
  作者：Ravil I. Khusnutdinov、Tatyana M. Oshnyakova

  DOI：10.1016/j.tetlet.2015.09.131

  日期：2015.11

  The amidation of norbornene with various nitriles was performed in the presence of water under the action of FeCl3·6H2O to give N-(exo-2-norbornyl)acylamides in 76–95% yield.

  在水存在下，在FeCl 3 ·6H 2 O的作用下，将降冰片烯与各种腈酰胺化，以76-95％的收率得到N-（exo -2-norbornyl）acylamide。
• Elemental fluorine. Part 14.1 Electrophilic fluorination and nitrogen functionalisation of hydrocarbons
  作者：Richard D. Chambers、Alan M. Kenwright、Mandy Parsons、Graham Sandford、John S. Moilliet

  DOI：10.1039/b204776b

  日期：2002.10.1

  achieved by reaction with either elemental fluorine or Selectfluor™, an electrophilic fluorinating reagent of the N–F class. An electrophilic mechanism is envisaged. On prolonged reaction, the strongly acidic reaction medium that is formed upon substitution of hydrogen by fluorine when Selectfluor™ is used as the fluorinating reagent, promotes loss of fluoride from the initial fluorinated product. Trapping

  可选择的 氟化作用 的范围 碳氢化合物 通过与任何一个反应来实现 元素氟或Selectfluor™，一种N-F级的亲电氟化试剂。设想了亲电机理。在长时间的反应中，当Selectfluor™用作氟化试剂时，氢被氟取代时形成的强酸性反应介质会促进氟化物从初始氟化产物中损失。乙腈捕集后续碳正离子溶剂 在Ritter类型的过程中给出了总体 氮 功能化 碳氢化合物。酰胺化碳氢化合物 也可以通过 烃 含氟和路易斯酸，例如三氟化硼乙醚， 在 乙腈。
• Alder; Stein, Justus Liebigs Annalen der Chemie, 1934, vol. 514, p. 197,200, 208
  作者：Alder、Stein

  DOI：——

  日期：——
• Reactions of Thianthrene Cation Radical with Acyclic and Cyclic Alcohols
  作者：Henry J. Shine、Wang Yueh

  DOI：10.1021/jo00092a011

  日期：1994.7

  Thianthrene cation radical perchlorate (Th*(ClO4-)-Cl-+) reacted readily with cycloalkanols (C-5, C-7, C-8, and C-12), alkan-2-ols (C-3, C-5, C-6, and C-8), 3-hexanol, neopentyl alcohol, a number of benzyl alcohols, dl- and (S)-1-phenylethanol, cyclopentyl- and cyclohexylmethanols, the exo- and endo-borneols, and norborneols. Reactions were carried out with an excess of the alcohol in acetonitrile solution containing 2,6-di-tert-butyl-4-methylpyridine. Products were alkenes, ethers, and N-substituted acetamides, depending on the structure of the alcohol. Thianthrene(Th) and its 5-oxide (ThO) were formed in equal amounts. The sum of amounts of products from the alcohol was equal to the amount of ThO. All reactions are interpretable on the basis of the ultimate formation and further reactions of a 5-alkoxythianthreniumyl ion (ROTh(+)). The predominant formation of nortricyclene from the norborneols is striking and is discussed. Swern-Moffatt-type oxidations of the alcohols were not observed.