2-(3,4-methylenedioxyphenyl)-1-phenylethanamine | 179397-86-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(3,4-methylenedioxyphenyl)-1-phenylethanamine
• 英文别名: 2-benzo[1,3]dioxol-5-yl-1-phenyl-ethylamine；2-Benzo[1,3]dioxol-5-yl-1-phenyl-aethylamin；1-phenyl-2-(benzo[1,3]dioxol-5-yl)-ethylamine；Phenethylamine, 3,4-methylenedioxy-alpha-phenyl-；2-(1,3-benzodioxol-5-yl)-1-phenylethanamine
• CAS: 179397-86-5
• 化学式: C₁₅H₁₅NO₂
• mdl: MFCD01708023
• 分子量: 241.29
• InChiKey: UYTHWQMJKBSROW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,4-methylenedioxyphenyl)-1-phenylethanamine 、 乙酸酐 生成 N-(2-benzo[1,3]dioxol-5-yl-1-phenyl-ethyl)-acetamide
  参考文献：
  名称：

  Dey; Ramanathan, Proceedings of the National Institute of Sciences of India, 1943, vol. 9, p. 193,222

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-5-styrylbenzo[d][1,3]dioxole 在 对苯二腈 、 氨 作用下， 以 水 、 乙腈 、 苯 为溶剂， 反应 20.0h， 以21%的产率得到2-(3,4-methylenedioxyphenyl)-1-phenylethanamine
  参考文献：
  名称：

  Regiochemistry on photoamination of stilbene derivatives with ammonia via electron transfer

  摘要：

  The regiochemistry of photoamination of 1,2-diarylethene (1) with ammonia in the presence of p-dicyanobenzene (DCNB) has been investigated. The photoamination of stilbene and p,p'-dimethoxystilbene gave 1-amino-1,2-diphenylethane and 1-amino-1,2-bis(p-methoxyphenyl)ethane, respectively. The photoamination of unsymmetric 1-aryl-2-phenylethene having an alkoxy group on the para position occurred selectively to give 1-amino-2-aryl-1-phenylethane. On the other hand, the photoamination of 1-aryl-2-phenylethene having a methyl and chloro group on the para position or methoxy group on the meta and ortho positions gave both 1-amino-2-aryl-1-phenylethane and 1-amino-1-aryl-2-phenylethane. The regiochemistry is related with the distribution of positive charge in the cation radicals of 1 generated from photochemical electron transfer to DCNB.

  DOI：

  10.1021/jo00031a010

文献信息

• Conformational analysis of 1,2,3,4-tetrahydroisoquinolines
  作者：Adriana F. Ibañez、Graciela Y. Moltrasio Iglesias、José M. Delfino

  DOI：10.1002/jhet.5570330209

  日期：1996.3

  conformer and the le′3e conformer are always large (3.80–6.10 kcal/mole for the NHe conformers and 3.60–3.80 kcal/mole for the NHa conformers). The lack of a γ1a upfield shift at C3 also points to the preference for the pseudoequatorial-equatorial conformer. For N-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline a preference for the NMe group in the equatorial position is predicted (0.60–2.00 kcal/mole)

  环和氮的反转解释了3-苯基-1、2,3、4-四氢异喹啉的构象平衡。为了量化每个构象异构体对平衡的相对贡献，我们对几种取代的3-苯基-1、2、3、4-四氢异喹啉进行了分子力学研究。根据cmr化学位移数据检查了来自计算的预测。没有船形显着促进平衡。我们计算的总体结果是，在所有情况下，赤道位置的3-苯基均受到强烈青睐（至少2.50 kcal / mole）。对于在氮上没有取代的3-苯基-1、2、3、4-四氢异喹啉，尽管两者之间的能量差总是很小（0.30-1.10 kcal / mol），但赤道位置的NH比轴向构型的NH更可取。为了唯一的le'3e构象是顺式-1,3-二取代的化合物（至少99.8％）。la'3a构象异构体和le'3e构象异构体之间的计算出的能量差始终很大（NHE构象异构体为3.80–6.10 kcal / mol，NHa构象异构体为3.60–3.80 kcal / mol）。缺乏γ
• [EN] PROCESS FOR PREPARING HYDROCINNAMIC ALDEHYDES IN ENANTIOPURE OR ENANTIOMERICALLY ENRICHED FORM<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ALDÉHYDES HYDROCINNAMIQUES DE FORME ÉNANTIOPURE OU ÉNANTIOMÉRIQUEMENT ENRICHIE
  申请人：ENDURA SPA

  公开号：WO2010131274A1

  公开（公告）日：2010-11-18

  A process is described for preparing hydrocinnamic aldehydes in enantiopure or enantiomerically enriched form of Formula I, in which R is isopropyl or tert-butyl and R' is hydrogen, or R and R' when taken together are a methylenedioxolyl group, comprising the following steps: a) reacting the hydrocinnamic aldehyde of Formula I with the alcohol of Formula Il in enantiopure or enantiomerically enriched form to give the crystallized hemiacetal of Formula III, in which R, R' have the same meaning as Formula I and (*) indicates a stereogenic centre in the absence of a solvent or in one or more aprotic solvents or mixtures thereof with apolar solvents; b) recovering the hydrocinnamic aldehyde of Formula I in enantiopure or enantiomerically enriched form from the crystallized hemiacetal of Formula III and the aldehyde of opposite configuration in enantiopure or enantiomerically enriched form from the hemiacetal crystallization mother liquors. The invention also concerns a process for preparing the alcohol of Formula Il to be introduced into step a).

  描述了一种制备式I的羟基肉桂醛的过程，其中R是异丙基或叔丁基，R'是氢，或者当一起时R和R'是一个亚甲二氧苯基团，包括以下步骤：a)将式I的羟基肉桂醛与式II的醇在对映纯或对映富集形式中反应，得到结晶的半缩醛III的结晶体，其中R，R'的含义与式I相同，(*)表示在无溶剂或一个或多个无极性溶剂或与极性溶剂混合物中具有立体异构中心；b)从半缩醛III的结晶体中以对映纯或对映富集形式回收式I的羟基肉桂醛，同时从半缩醛结晶母液中回收对映纯或对映富集形式的相反构型的醛。该发明还涉及一种制备式II醇的过程，以引入到步骤a)中。
• Synthetische Versuche in der Isochinolinreihe I
  作者：A. Dobrowsky

  DOI：10.1007/bf01044198

  日期：——
• The Preparation of Substituted Diphenylethylamines and Diphenylethanolamines
  作者：Warren D. McPhee、Ernst S. Erickson

  DOI：10.1021/ja01208a028

  日期：1946.4
• Owari, Pharmaceutical Bulletin, 1953, vol. 1, p. 174
  作者：Owari

  DOI：——

  日期：——