(+/-)-1-(4-methylphenyl)-2-propenylamine | 688362-59-6

• 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: (+/-)-1-(4-methylphenyl)-2-propenylamine
• 英文别名: 1-(4-methylphenyl)-prop-2-en-1-amine；1-(p-tolyl)prop-2-en-1-amine；1-(4-Methylphenyl)prop-2-en-1-amine
• CAS: 688362-59-6
• 化学式: C₁₀H₁₃N
• 分子量: 147.22
• InChiKey: LELXCTMSPSFLDK-UHFFFAOYSA-N

物化性质

• 沸点：
  243.4±9.0 °C(Predicted)
• 密度：
  0.952±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(4-methylphenyl)-2-propenylamine 在 盐酸 、 [(DPEphos)Rh(COD)]BF₄ 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 50.0h， 生成 (1RS,2SR)-2-morpholino-1-(p-tolyl)propan-1-amine
  参考文献：
  名称：

  Regio- and Chemoselective Intermolecular Hydroamination of Allyl Imines for the Synthesis of 1,2-Diamines

  摘要：

  The synthesis of 1,2-diamines via a Rh-catalyzed intermolecular hydroamination of N-allyl imines with cyclic amines is presented. Coordinating groups proximal to the olefin bind to the catalyst and promote the transformation. The reaction affords 1,2-diamines in very good yields and is functional-group-tolerant and highly diastereoselective.

  DOI：

  10.1021/ja505794u
• 作为产物：
  描述：

  p-methylcinnamyl alcohol 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium hydroxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 48.25h， 生成 (+/-)-1-(4-methylphenyl)-2-propenylamine
  参考文献：
  名称：

  An efficient enzymatic approach to (S)-1-aryl-allylamines

  摘要：

  A range of 1-aryl-allylamines were prepared in moderate to excellent enantioselectivity (ee 63.5%-> 99.9%) using lipase B from a Candida antarctica catalyzed resolution of racemic amines. This is the first time that CaLB has been used for the resolution of 1-aryl-allylamines. Racemic amines were prepared starting from aromatic aldehydes with a [3,3]-sigmatropic rearrangement of the acyclic imidates as the key step followed by trichloroacetamidate hydrolysis. Aldehydes were converted into acrylic esters using Knoevenagel reaction. After reduction, the corresponding alcohols were used for the preparation of trichloroacetimidates, which were then used in an Overman rearrangement. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.004

文献信息

• Enantioselective synthesis of 1-aryl-2-propenylamines: a new approach to a stereoselective synthesis of the Taxol® side chain
  作者：Daniele Castagnolo、Silvia Armaroli、Federico Corelli、Maurizio Botta

  DOI：10.1016/j.tetasy.2004.01.035

  日期：2004.3

  lipase-catalysed resolution of the corresponding racemates. (R)-1-Phenyl-2-propenylamine was further synthesised into (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoic acid methyl ester, the side chain of Taxol®.

  通过脂肪酶催化的相应外消旋体的拆分，制备了各种高对映体纯度的取代的1-芳基-2-丙烯基胺。（- [R）-1-苯基-2-丙烯基胺进一步合成为（2 - [R，3小号）-3-苯甲酰氨基-2-羟基-3-苯基丙酸甲基酯，紫杉醇的侧链®。
• Synthesis of Unsymmetrical Vicinal Diamines via Directed Hydroamination
  作者：Byung Joo Lee、Andrew R. Ickes、Anil K. Gupta、Seth C. Ensign、Tam D. Ho、Anika Tarasewicz、Evan P. Vanable、Gregory D. Kortman、Kami L. Hull

  DOI：10.1021/acs.orglett.2c01911

  日期：2022.8.5

  found in biologically active molecules. The hydroamination of allyl amine derivatives is a powerful approach for the synthesis of substituted 1,2-diamines. Herein, the rhodium-catalyzed hydroamination of primary and secondary allylic amines using diverse amine nucleophiles, including primary, secondary, acyclic, and cyclic aliphatic amines to access a wide range of unsymmetrical vicinal diamines, is presented

  邻位二胺是生物活性分子中常见的基序。烯丙胺衍生物的加氢胺化是合成取代的 1,2-二胺的有效方法。在此，提出了使用不同的胺亲核试剂（包括伯胺、仲胺、无环脂肪胺和环状脂肪胺）对伯胺和仲烯丙胺进行铑催化的氢胺化，以获得各种不对称邻位二胺。通过快速合成几种生物活性分子和类似物，进一步证明了该方法的实用性。
• An efficient enzymatic approach to (S)-1-aryl-allylamines
  作者：Anamarija Knežević、Goran Landek、Irena Dokli、Vladimir Vinković

  DOI：10.1016/j.tetasy.2011.06.004

  日期：2011.5

  A range of 1-aryl-allylamines were prepared in moderate to excellent enantioselectivity (ee 63.5%-> 99.9%) using lipase B from a Candida antarctica catalyzed resolution of racemic amines. This is the first time that CaLB has been used for the resolution of 1-aryl-allylamines. Racemic amines were prepared starting from aromatic aldehydes with a [3,3]-sigmatropic rearrangement of the acyclic imidates as the key step followed by trichloroacetamidate hydrolysis. Aldehydes were converted into acrylic esters using Knoevenagel reaction. After reduction, the corresponding alcohols were used for the preparation of trichloroacetimidates, which were then used in an Overman rearrangement. (C) 2011 Elsevier Ltd. All rights reserved.
• Regio- and Chemoselective Intermolecular Hydroamination of Allyl Imines for the Synthesis of 1,2-Diamines
  作者：Andrew R. Ickes、Seth C. Ensign、Anil K. Gupta、Kami L. Hull

  DOI：10.1021/ja505794u

  日期：2014.8.13

  The synthesis of 1,2-diamines via a Rh-catalyzed intermolecular hydroamination of N-allyl imines with cyclic amines is presented. Coordinating groups proximal to the olefin bind to the catalyst and promote the transformation. The reaction affords 1,2-diamines in very good yields and is functional-group-tolerant and highly diastereoselective.