(+)-1-phenyl-N-(p-tolyl)prop-2-en-1-amine | 793726-45-1

• 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-phenyl-N-(p-tolyl)prop-2-en-1-amine
• 英文别名: N-(1-Phenyl-2-propenyl)-4-methylaniline；4-methyl-N-(1-phenylprop-2-enyl)aniline
• CAS: 793726-45-1
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: ULWWXDDBBCNOBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-苯基丙-2-烯-1-醇 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 吡啶 、 三乙烯二胺 、 (R)-1-naphthyl chiral phosphoramidite 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (+)-1-phenyl-N-(p-tolyl)prop-2-en-1-amine
  参考文献：
  名称：

  原位生成活化的环金属化铱催化剂后，芳香胺的对映选择性烯丙基化。

  摘要：

  DOI：

  10.1002/anie.200460276

文献信息

• Palladium(0)-Catalyzed Allylation of Highly Acidic and Nonnucleophilic Anilines. The Origin of Stereochemical Scrambling When Using Allylic Carbonates
  作者：Marcial Moreno-Mañas、Lurdes Morral、Roser Pleixats

  DOI：10.1021/jo980209j

  日期：1998.9.1

  nitroanilines are efficiently allylated under palladium catalysis using allyl carbonates as allylating reagents. A stereochemical study of the reactions of ethyl cis-5-methyl-2-cyclohexenylcarbonate with 4-nitro- and 2,4-dinitroaniline was performed. Bidentate phosphines as stabilizing ligands gave clean retention of configuration whereas triphenylphosphine permitted cis-trans isomerization of the allylic carbonate

  酸性苯胺（如二苯胺，吩噻嗪和硝基苯胺）在钯催化下使用碳酸烯丙酯作为烯丙基化试剂可以有效地烯丙基化。进行了立体化学研究顺式5-甲基-2-环己烯基碳酸乙酯与4-硝基和2,4-二硝基苯胺的反应。二齿膦作为稳定的配体，使构型保持清晰，而三苯膦则允许烯丙基碳酸酯的顺反异构化，烯丙基化反应发生在Curtin-Hammet预平衡条件下。
• Enantioselective Phosphoramidite Compounds and Catalysts
  申请人：Hartwig F. John

  公开号：US20070259774A1

  公开（公告）日：2007-11-08

  This invention relates to phosphoramidite compounds and catalyst complexes which can be used to provide enantioselective reactions including hydroamination reactions, etherification reactions and conjugate addition reactions and allylic substitution reactions, among others. In a first aspect, the present invention is directed to phosphoramidite and related compounds according to general structure (I), where Z is absent or is a group containing O, N or S, preferably O; R 1 and R 2 are independently an optionally substituted C 1-12 alkyl group, an optionally substituted (CH 2 ) n -aromatic group or (CH 2 ) n -heteroaromatic group, or are linked together to form an optionally substituted aliphatic or (CH 2 ) n -aromatic dianion of a diol, diamine, dithiol, aminoalcohol, aminohiolate or a alcoholthiol group; R 3′ and R 3 are each independently H, an optionally substituted C 1 -C 12 alkyl group or an optionally substituted (CH 2 ) n -aromatic group with the proviso that R 3′ and R 3 are not both H, or together R 3′ and R 3 form an optionally substituted C 5 -C 15 saturated or unsaturated carbocyclic ring; R 4 is H, an optionally substituted C 1 -C 12 alkyl group or an optionally substituted (CH 2 ) n -aromatic group; R 5 is absent, H, an optionally substituted C 1 -C 12 alkyl group or an optionally substituted (CH 2 ) n -aromatic or (CH 2 ) n -heteroaromatic group; R a and R a′ are each independently H or a C 1 -C 3 alkyl group, or R a and R a′ together with the carbon to which they are attached form a optionally substituted C 5 -C 15 saturated or unsaturated carbocyclic or heterocyclic ring, or an aromatic or heteroaromatic ring; R 6 and R 7 are each independently H, an optionally substituted C 1 -C 12 alkyl group or an optionally substituted (CH 2 ) n -aromatic group, with the proviso that R 5 , R 6 and R 7 cannot simultaneously be H, and when R a and R a′ , together with the carbon to which they are attached, form a carbocyclic ring, heterocyclic ring or an aromatic or heteroaromatic ring, R 5 is absent or is preferably H; R 6 and R 7 are preferably H or CH 3 ; and each n is independently 0, 1, 2, 3, 4, 5 or 6 and wherein at least one of the carbon atoms attached to the nitrogen of the phosphoramidite group is a chiral center.

  本发明涉及磷酰胺类化合物和催化剂复合物，可用于提供对映选择性反应，包括羟胺化反应、醚化反应和共轭加成反应以及联烯取代反应等。在第一个方面，本发明涉及磷酰胺和相关化合物，其一般结构如下（I），其中Z不存在或是包含O、N或S的基团，优选为O；R1和R2分别为可选取代的C1-12烷基、可选取代的（CH2）n-芳基或（ ）n-杂芳基，或相互连接形成可选取代的脂肪族或（ ）n-芳香基的二阴离子的二元醇、二胺、二硫醇、氨基醇、氨基硫醇或醇硫基基团；R3'和R3各自独立地为H、可选取代的C1-C12烷基或可选取代的（ ）n-芳基，但须满足R3'和R3不能同时为H，或者R3'和R3共同形成可选取代的C5-C15饱和或不饱和的碳环；R4为H、可选取代的C1-C12烷基或可选取代的（ ）n-芳基；R5不存在、为H、可选取代的C1-C12烷基或可选取代的（ ）n-芳基或（ ）n-杂芳基；Ra和Ra'各自独立地为H或C1-C3烷基，或者Ra和Ra'与它们附着的碳共同形成可选取代的C5-C15饱和或不饱和的碳环或杂环，或芳香或杂芳环；R6和R7各自独立地为H、可选取代的C1-C12烷基或可选取代的（ ）n-芳基，但须满足R5、R6和R7不能同时为H，且当Ra和Ra'与它们附着的碳共同形成碳环、杂环或芳香或杂芳环时，R5不存在或优选为H；R6和R7优选为H或CH3；每个n独立地为0、1、2、3、4、5或6，其中至少有一个连接到磷酰胺基团氮上的碳原子是手性中心。