(E)-N-(hex-2-en-1-yl)aniline | 351387-10-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-N-(hex-2-en-1-yl)aniline
• 英文别名: (E)-N-(2-hexenyl)aniline；N-[(E)-hex-2-enyl]aniline
• CAS: 351387-10-5
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: ZRCXVUQKIIGSQF-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-(hex-2-en-1-yl)aniline 在 N-叔丁基苯硫腈氯化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以66%的产率得到
  参考文献：
  名称：

  N-叔丁基苯基亚磺酰亚胺酰氯氧化各种仲胺为亚胺

  摘要：

  通过使用 N-叔丁基苯基亚磺酰亚胺酰氯和 DBU，各种仲胺在 -78 °C 下顺利氧化为相应的亚胺。

  DOI：

  10.1246/cl.2001.390
• 作为产物：
  描述：

  反式-2-已烯-1-醇 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 吡啶 、 正丙胺 、 (R)-O,O'-BINAP-N,N-[(R)-1-(1-naphthyl)ethyl]2phosphoramidite 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-N-(hex-2-en-1-yl)aniline
  参考文献：
  名称：

  Effects of Catalyst Activation and Ligand Steric Properties on the Enantioselective Allylation of Amines and Phenoxides

  摘要：

  The yields, enantioselectivities, and regioselectivities of the reactions of amines and phenoxides with allylic carbonates in the presence of a metallacyclic iridium catalyst were compared. These data show that both preactivation of the catalyst and the size of the ligand affect the yield, enantioselectivity, and regioselectivity. With the activated catalyst containing a bis-naphthethylamino group, the allylic amination and etherification of a broad range of allylic carbonates occurred in high yields and with high regioselectivities and enantioselectivities.

  DOI：

  10.1021/ol050029d

文献信息

• N-Alkylation of amines with alcohols over nanosized zeolite beta
  作者：Marri Mahender Reddy、Macharla Arun Kumar、Peraka Swamy、Mameda Naresh、Kodumuri Srujana、Lanka Satyanarayana、Akula Venugopal、Nama Narender

  DOI：10.1039/c3gc41345d

  日期：——

  Direct N-alkylation of amines with alcohols was successfully performed by using nanosized zeolite beta, which showed the highest catalytic activity among other conventional zeolites. This method has several advantages, such as eco-friendliness, moderate to high yields, and simple work-up procedure. The catalyst was successfully recovered and reused without significant loss of activity and only water is produced as co-product. In addition, imines were also efficiently prepared from the tandem reactions of amines with 2-, 3- and 4-nitrobenzyl alcohols using nanosized zeolite beta.

  使用纳米尺寸的Beta沸石成功实现了胺与醇的直接N-烷基化反应，Beta沸石在其他传统沸石中显示出最高的催化活性。该方法具有多个优点，如环保性、适中至高产率以及简便的后续处理程序。催化剂可成功回收并重复使用，活性无明显损失，副产物仅为水。此外，通过使用纳米尺寸的Beta沸石，胺与2-、3-和4-硝基苄醇的串联反应也能高效制备亚胺。
• BF₃·Et₂O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant
  作者：Zhenli Luo、Yixiao Pan、Zhen Yao、Ji Yang、Xin Zhang、Xintong Liu、Lijin Xu、Qing-Hua Fan

  DOI：10.1039/d1gc01468d

  日期：——

  direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the

  在廉价的 BF 3 ·Et 2催化下，使用甲酸作为还原剂的醛与胺的通用无金属和无碱直接还原胺化O 已开发。广泛的伯胺和仲胺以及不同取代的醛与这种转化相容，从而可以轻松获得各种仲胺和叔胺，高产率和广泛的官能团耐受性。此外，该方法有利于生物活性化合物的后期功能化以及商业化药物分子和生物相关氮杂环的制备。该工艺操作简单，易于放大，不需要干燥条件、惰性气氛或除水剂。机理研究揭示了 BF 3对亚胺的活化和甲酸的氢化物转移的参与。
• One-pot synthesis of α-aminophosphonates via a cascade sequence of allylamine isomerization/hydrophosphonylation
  作者：Liu-Liang Mao、Chen-Chen Li、Qiang Yang、Ming-Xing Cheng、Shang-Dong Yang

  DOI：10.1039/c7cc01391d

  日期：——

  A Rh/Ni-catalyzed cascade sequence of allylamine isomerization and hydrophosphonylation to synthesize [small alpha]-aminophosphonates has been disclosed.

  已经公开了Rh / Ni催化的烯丙胺异构化和氢膦酰化以合成α-氨基膦酸酯的级联序列。
• Diastereoselective Aminooxygenation and Diamination of Alkenes with Amidines by Hypervalent Iodine(III) Reagents
  作者：Hui Chen、Atsushi Kaga、Shunsuke Chiba

  DOI：10.1021/ol503000c

  日期：2014.12.5

  Diastereoselective anti-aminooxygenation and anti-diamination of alkenes with amidines were enabled by hypervalent iodine(III) reagents such as PhI(OCOR)2 and PhI(NMs2)2, respectively. The present transformation offers diastereochemically pure dihydroimidazoles divergently from E- and Z-alkenes.

  非对映选择性的抗-aminooxygenation和抗与脒烯烃-diamination由高价碘（III）试剂如岛（OCOR）启用2和phi（NMS 2）2，分别。本转化提供了不同于E-和Z-烯烃的非对映化学纯二氢咪唑。
• (π-Allyl)palladium Complexes Bearing Diphosphinidenecyclobutene Ligands (DPCB):  Highly Active Catalysts for Direct Conversion of Allylic Alcohols
  作者：Fumiyuki Ozawa、Hideyuki Okamoto、Seiji Kawagishi、Shogo Yamamoto、Tatsuya Minami、Masaaki Yoshifuji

  DOI：10.1021/ja0274406

  日期：2002.9.1

  The (pi-allyl)palladium complex bearing an sp2-hybridized phosphorus ligand (DPCB-OMe: 1,2-bis(4-methoxyphenyl)-3,4-bis[(2,4,6-tri-tert-butylphenyl)phosphinidene]cyclobutene) efficiently catalyzes direct conversion of allylic alcohols in the absence of activating agents of alcohols such as Lewis acids. N-Allylation of aniline proceeds at room temperature to afford monoallylated anilines in 90-97% yields

  带有 sp2-杂化磷配体的（pi-烯丙基）钯配合物（DPCB-OMe：1,2-双（4-甲氧基苯基）-3,4-双[（2,4,6-三叔丁基苯基）在不存在醇（例如路易斯酸）的活化剂的情况下，膦亚基]环丁烯）有效地催化烯丙醇的直接转化。苯胺的 N-烯丙基化在室温下进行，以 90-97% 的产率得到单烯丙基化的苯胺。使用催化量的吡啶作为碱，活性亚甲基化合物的 C-烯丙基化也在 50 摄氏度下成功，以 85-95% 的产率得到单烯丙基化产物。涉及氢化和（π-烯丙基）钯中间体的催化机制已根据使用假定中间体的模型化合物进行的化学计量检验提出。