(1R,2RS,4R)-camphane-2-amine hydrochloride

• 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: (1R,2RS,4R)-camphane-2-amine hydrochloride
• 英文别名: 1,7,7Trimethylbicyclo[2.2.1]heptan-2-amine hydrochloride；(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-amine;hydrochloride
• 化学式: C₁₀H₁₉N*ClH
• 分子量: 189.728
• InChiKey: XVVITZVHMWAHIG-VMKQZJJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2RS,4R)-camphane-2-amine hydrochloride 、 4-氯苯甲酰氯 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 72.33h， 以88%的产率得到N-{(1R,2RS)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl}-4-chlorobenzamide
  参考文献：
  名称：

  Synthesis of New Camphane-Type Amides: Potential Synthetic Adaptogenes

  摘要：

  A significant effect of the steric factor on the activity of 3,5-dimethyl-1H-pyrazolide as an acylating agent has been found using the example of acylation of camphane-type monoamines. The predominant contribution of the catalytic hydrogenation as a component of the Schwenk-Papa reaction has been confirmed by the synthesis of 4-chlorobenzoyl derivatives.

  DOI：

  10.1134/s1070363219030058
• 作为产物：
  描述：

  (1R)-樟脑肟 在 NiAl₂ 、 potassium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 、 甲基叔丁基醚 为溶剂， 以81%的产率得到(1R,2RS,4R)-camphane-2-amine hydrochloride
  参考文献：
  名称：

  Potential Synthetic Adaptogens: V. Synthesis of Cage Monoamines by the Schwenk–Papa Reaction

  摘要：

  The reduction of cage ketoximes under Schwenk-Papa reaction conditions was studied to establish that the D,L, D- and L-camphor oximes are smoothly reduced to the corresponding amines in high yields. At the same time, D,L-norcamphor and adamantan-2-one oximes undergo partial catalytic deoximation to form a mixture of the corresponding amines and alcohols.

  DOI：

  10.1134/s1070428019110162

文献信息

• Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: IX. N-(1,7,7-Trimethylbicyclo[2.2.1]heptan-2-yl) Ureas and Thioureas
  作者：Ya. P. Kuznetsov、E. K. Degtyarenko、V. V. Burmistrov、M. H. Abbas Saeef、D. A. Pitushkin、A. A. Vernigora、G. M. Butov

  DOI：10.1134/s1070428021040035

  日期：2021.4

  thioureas containing a lipophilic optically active natural bicyclic moiety have been synthesized by reactions of (R)-, (S)-, and (RS)-1,1,7-trimethylbicyclo[2.2.1]heptan-2-amines with aromatic isocyanates and isothiocyanates in up to 85% and 88% yield, respectively, with the goal of estimating enantiomeric stereospecificity of human soluble epoxide hydrolase (hsEH). The synthesized compounds are promising

  通过 (R)-、(S)- 和 (RS)-1,1,7-三甲基双环的反应合成了 N,N'-二取代脲和含有亲油性光学活性天然双环部分的硫脲[2.2.1]庚烷-2-胺与芳族异氰酸酯和异硫氰酸酯的产率分别高达 85% 和 88%，目的是估计人可溶性环氧化物水解酶 (hsEH) 的对映体立体特异性。合成的化合物有望作为 RNA 病毒和 hsEH 的抑制剂。
• Potential Synthetic Adaptogens: V. Synthesis of Cage Monoamines by the Schwenk–Papa Reaction
  作者：I. A. Novakov、M. B. Nawrozkij、A. S. Mkrtchyan、S. N. Voloboev、O. V. Vostrikova、A. A. Vernigora、R.V. Brunilin

  DOI：10.1134/s1070428019110162

  日期：2019.11

  The reduction of cage ketoximes under Schwenk-Papa reaction conditions was studied to establish that the D,L, D- and L-camphor oximes are smoothly reduced to the corresponding amines in high yields. At the same time, D,L-norcamphor and adamantan-2-one oximes undergo partial catalytic deoximation to form a mixture of the corresponding amines and alcohols.
• Synthesis of New Camphane-Type Amides: Potential Synthetic Adaptogenes
  作者：I. A. Novakov、R. V. Brunilin、G. M. Butov、A. A. Vernigora、M. B. Navrotskii、A. S. Yablokov、S. N. Voloboev

  DOI：10.1134/s1070363219030058

  日期：2019.3

  A significant effect of the steric factor on the activity of 3,5-dimethyl-1H-pyrazolide as an acylating agent has been found using the example of acylation of camphane-type monoamines. The predominant contribution of the catalytic hydrogenation as a component of the Schwenk-Papa reaction has been confirmed by the synthesis of 4-chlorobenzoyl derivatives.