(E)-N,2-dimethyl-3-phenylprop-2-en-1-amine | 98978-21-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-N,2-dimethyl-3-phenylprop-2-en-1-amine
• 英文别名: Methyl(2-methyl-3-phenylprop-2-en-1-yl)amine, trans
• CAS: 98978-21-3
• 化学式: C₁₁H₁₅N
• 分子量: 161.247
• InChiKey: BNPOQSIKPUBUEH-CSKARUKUSA-N

物化性质

• 沸点：
  262.8±19.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N,2-dimethyl-3-phenylprop-2-en-1-amine 、 (氯甲基)萘 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到(E)-N-methyl-N-(2-methyl-3-phenyl-2-propenyl)-1-naphthalenemethanamine
  参考文献：
  名称：

  Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics

  摘要：

  Naftifine (1) is the first representative of the new antifungal allylamine derivatives. Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals. A tertiary allylamine function seems to be a prerequisite for activity against fungi. By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations. Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.

  DOI：

  10.1021/jm00151a019
• 作为产物：
  描述：

  反式-alpha-甲基肉桂醛 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (E)-N,2-dimethyl-3-phenylprop-2-en-1-amine
  参考文献：
  名称：

  Photoenzymatic Synthesis of α-Tertiary Amines by Engineered Flavin-Dependent “Ene”-Reductases

  摘要：

  DOI：

  10.1021/jacs.1c09828

文献信息

• A General Acid‐Mediated Hydroaminomethylation of Unactivated Alkenes and Alkynes
  作者：Daniel Kaiser、Veronica Tona、Carlos R. Gonçalves、Saad Shaaban、Alberto Oppedisano、Nuno Maulide

  DOI：10.1002/anie.201906910

  日期：2019.10.7

  its considerable potential to streamline amine synthesis. State-of-the-art protocols for hydroaminomethylation of alkenes rely largely on transition-metal catalysis, enabling this transformation only under highly designed and controlled conditions. Here we report a broadly applicable, acid-mediated approach to the hydroaminomethylation of unactivated alkenes and alkynes. This methodology employs cheap

  与广泛研究的金属催化加氢胺化反应相比，加氢氨甲基化尽管具有极大的简化胺合成的潜力，但受到的关注却很少。烯烃加氢氨基甲基化的最新方案主要依赖于过渡金属催化，只有在高度设计和控制的条件下才能进行这种转化。在这里，我们报告了一种广泛适用的酸介导的方法，用于未活化的烯烃和炔烃的氢氨基甲基化。该方法采用廉价，易于获得且稳定的反应物，并提供所需的胺，且具有出色的官能团耐受性和无可挑剔的区域选择性。报道了这种转变的广泛范围，以及机理研究和原位多米诺骨牌功能化反应。
• Palladium-Catalyzed γ,γ′-Diarylation of Free Alkenyl Amines
  作者：Vinod G. Landge、Aaron J. Grant、Yu Fu、Allison M. Rabon、John L. Payton、Michael C. Young

  DOI：10.1021/jacs.1c04261

  日期：2021.7.14

  multiple C–C bonds in one-pot using a single functional group. The regioselective dicarbofunctionalization of alkenes is therefore an important area of research to rapidly obtain complex organic molecules. Herein, we report a palladium-catalyzed γ,γ′-diarylation of free alkenyl amines through interrupted chain walking for the synthesis of Z-selective alkenyl amines. Notably, while 1,3-dicarbofunctionalization

  烯烃的直接双官能化是使用单个官能团在一锅中构建多个 C-C 键的有效方法。因此，烯烃的区域选择性双碳功能化是快速获得复杂有机分子的重要研究领域。在此，我们报告了钯催化的游离链烯基胺的 γ,γ'-二芳基化反应，用于合成Z选择性链烯基胺。值得注意的是，虽然烯丙基的 1​​,3-二碳官能化是有先例的，但本公开允许高度取代的烯丙胺的 1,3-二碳官能化得到高Z-选择性三取代的烯烃产品。该级联反应通过未受保护的胺导向的 Mizoroki-Heck (MH) 途径进行，该途径具有 β-氢化物消除以选择性链行走以提供新的末端烯烃，然后在空间拥挤的烯丙基部分周围生成顺式选择性烯基胺。这种操作简单的协议适用于各种环状、支链和线性二级和三级烯胺，并且在芳烃偶联伙伴方面也具有广泛的底物范围。已经进行了机制研究以帮助阐明该机制，包括可能存在非生产性的 C-H 侧激活途径。
• Clavulanic acid derivatives and process for their preparation
  申请人：BEECHAM GROUP PLC

  公开号：EP0009302A1

  公开（公告）日：1980-04-02

  The present invention provides a process for the preparation of a compound of the formula (I): wherein R1 is a hydrogen atom, an alkyl group of up to 5 carbon atoms, a cycloalkyl group of 5 or 6 carbon atoms, a hydroxyalkyl group of up to 5 carbon atoms or a moiety of the sub formula (a): wherein R2 is a hydrogen, fluorine, chlorine or bromine atom or an alkyl group of 1-3 carbon atoms, an alkoxyl group of 1-3 carbon atoms, an acyloxyl group of 1-3 atoms, a hydroxyl group, an alkoxycarbonyl group containing 1-3 carbon atoms in the alkoxy part, or a group -N(Rs)CO . R6, -N(R5)SO2R6 or -CO-NRsR6 where R5 is a hydrogen atom or an alkyl group of 1-3 carbon atoms or a phenyl or benzyl group and R6 is an alkyl group of 1-3 carbon atoms or a phenyl or benzyl group: R3 is a hydrogen, fluorine or chlorine atom or an alkyl group of 1-3 carbon atoms, an alkoxyl group of 1-3 carbon atoms or an acyloxyl group of 1-3 carbon atoms; and R4 is a hydrogen fluorine or chlorine atom or an alkyl group of 1-3 carbon atoms or an alkoxyl group of 1-3 carbon atoms. The disclosed process comprises inter alia the hydrogenation of a compound of the formula (II): or a hydrogenolysable ester thereof wherein R1 is as defined in relation to formula (I) or R1 is R'1 a moiety that on hydrogenation provides a group R1 as defined in formula (I), R8 is a lower atom or a lower alkyl group and R10 is a hydrogen atom or a lower alkyl or phenyl group. The compounds of the formula (III) are useful intermediates and as such form part of this invention.

  本发明提供了一种制备式(I)化合物的工艺： 其中 R1 是氢原子、最多 5 个碳原子的烷基、5 或 6 个碳原子的环烷基、最多 5 个碳原子的羟烷基或亚式（a）的分子： 其中 R2 是氢、氟、氯或溴原子或 1-3 个碳原子的烷基、1-3 个碳原子的烷氧基、1-3 个原子的酰氧基、羟基、烷氧基部分含有 1-3 个碳原子的烷氧羰基或基团 -N(Rs)CO .R6、-N(R5)SO2R6 或 -CO-NRsR6 其中 R5 是氢原子或 1-3 个碳原子的烷基或苯基或苄基，R6 是 1-3 个碳原子的烷基或苯基或苄基：R3是氢、氟或氯原子或1-3个碳原子的烷基、1-3个碳原子的烷氧基或1-3个碳原子的酰氧基；R4是氢氟或氯原子或1-3个碳原子的烷基或1-3个碳原子的烷氧基。所公开的工艺包括将式（II）化合物氢化： 或其可氢解酯，其中 R1 如式 (I) 所定义，或 R1 是 R'1 的分子，氢化后可得到如式 (I) 所定义的基团 R1，R8 是低级原子或低级烷基，R10 是氢原子或低级烷基或苯基。式（III）化合物是有用的中间体，因此构成本发明的一部分。
• PRODUCTION OF AMINES VIA A HYDROAMINOMETHYLATION REACTION
  申请人：Universität Wien

  公开号：EP3569593A1

  公开（公告）日：2019-11-20

  Provided is a process for producing an amine via a hydroaminomethylation reaction of a non-aromatic C-C double bond or C-C triple bond, said process comprising a step of reacting a compound comprising a non-aromatic C-C double bond or C-C triple bond with a reactive component which is obtainable by combining an aminal with an acidic medium comprising trifluoroacetic acid, wherein the aminal contains two amino groups independently selected from a secondary and a tertiary amino group that are linked by a methylene group, and at least one of the amino groups carries a hydrogen atom at a carbon atom bound in α-position to its nitrogen atom.

  提供了一种通过非芳香族 C-C 双键或 C-C 三键的氢氨甲基化反应生产胺的工艺，所述工艺包括 使包含非芳香族 C-C 双键或 C-C 三键的化合物与反应组分反应的步骤，该反应组分可通过将氨基醛与包含三氟乙酸的酸性介质结合而获得、 其中氨基醛含有两个独立地选自仲氨基和叔氨基的氨基基团，这两个氨基基团通过亚甲基连接，并且至少有一个氨基基团的碳原子上带有一个氢原子，该氢原子以 α 位与氮原子结合。
• Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics
  作者：Anton Stuetz、Apostolos Georgopoulos、Waltraud Granitzer、Gabor Petranyi、Daniel Berney

  DOI：10.1021/jm00151a019

  日期：1986.1

  Naftifine (1) is the first representative of the new antifungal allylamine derivatives. Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals. A tertiary allylamine function seems to be a prerequisite for activity against fungi. By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations. Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.