N-(3-methyl-cyclohexyl)-p-phenetidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(3-methyl-cyclohexyl)-p-phenetidine
• 英文别名: N-(3-Methyl-cyclohexyl)-p-phenetidin；3-p-Phenetidino-1-methyl-cyclohexan；4-ethoxy-N-(3-methylcyclohexyl)aniline
• 化学式: C₁₅H₂₃NO
• mdl: MFCD11121890
• 分子量: 233.354
• InChiKey: ZNYFTENBTASTDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-methyl-cyclohexyl)-p-phenetidine 在 硫酸 、 水 、 高碘酸 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以90%的产率得到3-甲基环己胺
  参考文献：
  名称：

  Synthesis of trans-3-Substituted Cyclohexylamines via Brønsted Acid Cata­lyzed and Substrate-Mediated Triple Organocatalytic Cascade Reaction

  摘要：

  我们报告了一种新的有机催化级联反应。胺底物与催化量的布氏酸相结合，在一个新的有机催化级联反应中将烯胺催化和亚胺催化与布氏酸催化合二为一。我们发现，苯胺底物本身与催化量的 PTSA-H2O 结合可作为胺催化剂，完成醛醇缩合-共轭物还原级联反应，最后在布氏酸催化下还原胺化，将胺底物纳入最终产物。这一转化过程能以良好的产率和非对映选择性生成反式-3-取代的环己胺。

  DOI：

  10.1055/s-2007-984877
• 作为产物：
  描述：

  1-溴-3-甲基环己烷 、 对乙氧基苯胺 生成 N-(3-methyl-cyclohexyl)-p-phenetidine
  参考文献：
  名称：

  Loevenich et al., Chemische Berichte, 1929, vol. 62, p. 3095

  摘要：

  DOI：

文献信息

• Organocatalytic Asymmetric Reaction Cascade to Substituted Cyclohexylamines
  作者：Jian Zhou、Benjamin List

  DOI：10.1021/ja072134j

  日期：2007.6.1

  We report a new strategy for organocatalytic cascade reactions. Accordingly, enamine catalysis, iminium catalysis, and Bronsted acid catalysis can work in concert in a highly enantioselective organocatalytic cascade sequence toward chiral cis-3-substituted cyclohexylamines. We found that an achiral amine in combination with a catalytic amount of a chiral Bronsted acid can accomplish an aldol additi

  我们报告了一种有机催化级联反应的新策略。因此，烯胺催化、亚胺鎓催化和布朗斯台德酸催化可以在高度对映选择性的有机催化级联序列中协同作用，形成手性顺式 3-取代环己胺。我们发现，非手性胺与催化量的手性布朗斯台德酸结合可以完成醛醇加成-脱水-共轭还原-还原胺化，以良好的产率和出色的对映选择性提供药物活性化合物的潜在中间体。
• [EN] PURINE DERIVATIVES AND THEIR USE AS PHARMACEUTICALS FOR PREVENTION OR TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] DÉRIVÉS DE PURINE ET LEUR UTILISATION COMME PRODUITS PHARMACEUTIQUES POUR PRÉVENIR OU TRAITER LES INFECTIONS BACTÉRIENNES
  申请人：BIODIM LAB

  公开号：WO2012172043A1

  公开（公告）日：2012-12-20

  The invention relates to the compounds of general formula (I) and their addition salts thereof with acids and bases: wherein A is phenyl, naphthyl and 5-10 membered monocyclic or bicyclic unsaturated heterocycle, optionally substituted by a group R1 which is as defined in the application and is itself optionally substitutes by a group R2 which is as defined in the application and is itself optionally substituted by a group R3 which is defined in the application, Y and W, identical or different, are H, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, phenyl or 4-10 monocyclic or bicyclic saturated or unsaturated heterocycle, optionally substituted by R1, or Y and/or W form a 4-10 membered cycle with R1, or Y and W form with N a saturated or unsaturated nitrogenous 4-10 membered mono, bi or tricyclic system, fused, bridged or spiro system, said system being optionally substituted by R1, said system being different from morpholine, with the proviso that when Y and A are phenyl or heterocycle, W is not H, a process and intermediates for their preparation and their use in the antibacterial prevention and therapy, used alone or in association with antibacterials, antivirulence agents or drugs reinforcing the host innate immunity, and pharmaceutical compositions and associations containing them.
• Loevenich et al., Chemische Berichte, 1929, vol. 62, p. 3095
  作者：Loevenich et al.

  DOI：——

  日期：——
• Synthesis of <i>trans</i>-3-Substituted Cyclohexylamines via Brønsted Acid Cata­lyzed and Substrate-Mediated Triple Organocatalytic Cascade Reaction
  作者：Benjamin List、Jian Zhou

  DOI：10.1055/s-2007-984877

  日期：——

  We report a new organocatalytic cascade reaction. A combination of the amine substrate with a catalytic amount of a Brønsted acid merges enamine and iminium catalysis with Brønsted acid catalysis in a new organocatalytic cascade reaction. We found that the aniline substrate itself in combination with a catalytic amount of PTSA·H2O can function as an aminocatalyst accomplishing an aldol condensation-conjugate reduction cascade, which ­terminates in a Brønsted acid catalyzed reductive amination incorporating the amine substrate into the final product. This transformation furnishes trans-3-substituted cyclohexyl amines in good yields and good diastereoselectivities.

  我们报告了一种新的有机催化级联反应。胺底物与催化量的布氏酸相结合，在一个新的有机催化级联反应中将烯胺催化和亚胺催化与布氏酸催化合二为一。我们发现，苯胺底物本身与催化量的 PTSA-H2O 结合可作为胺催化剂，完成醛醇缩合-共轭物还原级联反应，最后在布氏酸催化下还原胺化，将胺底物纳入最终产物。这一转化过程能以良好的产率和非对映选择性生成反式-3-取代的环己胺。