d-benzylphenyl-allylmethylammonium iodide | 7620-82-8

• 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: d-benzylphenyl-allylmethylammonium iodide
• 英文别名: (+)-N-allyl-N-benzyl-N-methyl-anilinium; iodide；(+)-N-Allyl-N-benzyl-N-methyl-anilinium; Jodid；(+)-Allylbenzyl-methylphenylammonium iodide；benzyl-methyl-phenyl-prop-2-enylazanium;iodide
• CAS: 7620-82-8；25458-39-3
• 化学式: C₁₇H₂₀N*I
• 分子量: 365.257
• InChiKey: JZMQDCAWXAADCI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  d-benzylphenyl-allylmethylammonium iodide 生成 N-烯丙基-n-甲基苯胺 、 苄基碘
  参考文献：
  名称：

  Wedekind,E., Chemische Berichte, 1902, vol. 35, p. 766

  摘要：

  DOI：
• 作为产物：
  描述：

  N-烯丙基-n-甲基苯胺 在 sodium iodide 作用下， 反应 168000.0h， 生成 d-benzylphenyl-allylmethylammonium iodide
  参考文献：
  名称：

  Lamellar Racemic Twinning as an Obstacle for the Resolution of Enantiomers by Crystallization:  The Case of Me(All)N⁺(CH₂Ph)Ph X^- (X = Br, I) Salts

  摘要：

  Ammonium salts Me(All)N+(CH2Ph)Ph X- (X = Br, 1; X = I, 2) (Asymmetric nitrogen, communication 89, prev. see Kostyanovsky, R. G.; Kostyanovsky, V. R.; Kadorkina, G. K.; Lyssenko, K. A. Mendeleev Commun. 2003, 111) were historically the first compounds with a chiral nitrogen center obtained in optically pure forms via diastereoisomers. We were astonished by the fact that W. J. Pope, who first carried out the resolution (1899), mentioned in his articles that salts have features for conglomerate formation but nowhere did he note the registration of optical activity and manual sorting of left- and right-handed single crystals. We reinvestigated these salts with the help of X-ray diffraction and found that the space groups of both of them are P2(1)2(1)2(1). However, despite the chiral space group, the enantiomeric composition of the majority of the crystals obtained by crystallization from solutions of racemates was found to be near racemic. Such crystal growth behavior, called lamellar twinning between enantiomers, represents a serious obstacle to the methods of enantiomeric resolution by straightforward crystallization that are used in the chiral industry. The phenomenon probably results from a high concentration in solution of heterochiral growth clusters, which promote the formation of the intergrowth region of twins. To glance experimentally at what might possibly be the first crystal growth units, electrospray ionization FT-ICR mass spectrometry was applied. We were able to register polyionic clusters containing up to five chiral cations. The relative stability of the simplest dimeric clusters (two cations linked by an anion) of 1 with homo- and heterochiral composition was estimated with a B3LYP/SDD calculation, and heterochiral one was found to be more stable by 0.883 kcal/mol.

  DOI：

  10.1021/jp035588l

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Hg: MVol.B1, 17, page 387 - 398
  作者：

  DOI：——

  日期：——
• Wedekind, Chemische Berichte, 1899, vol. 32, p. 521
  作者：Wedekind

  DOI：——

  日期：——
• LXXXVIII.—Optically active nitrogen compounds and their bearing on the valency of nitrogen. d- and 1-α-Benzylphenylallylmethylammonium salts
  作者：William Jackson Pope、Alfred William Harvey

  DOI：10.1039/ct9017900828

  日期：——
• US4268456A
  申请人：——

  公开号：US4268456A

  公开（公告）日：1981-05-19
• Lamellar Racemic Twinning as an Obstacle for the Resolution of Enantiomers by Crystallization:  The Case of Me(All)N⁺(CH₂Ph)Ph X^- (X = Br, I) Salts
  作者：Vladimir Yu. Torbeev、Konstantin A. Lyssenko、Oleg N. Kharybin、Mikhail Yu. Antipin、Remir G. Kostyanovsky

  DOI：10.1021/jp035588l

  日期：2003.12.1

  Ammonium salts Me(All)N+(CH2Ph)Ph X- (X = Br, 1; X = I, 2) (Asymmetric nitrogen, communication 89, prev. see Kostyanovsky, R. G.; Kostyanovsky, V. R.; Kadorkina, G. K.; Lyssenko, K. A. Mendeleev Commun. 2003, 111) were historically the first compounds with a chiral nitrogen center obtained in optically pure forms via diastereoisomers. We were astonished by the fact that W. J. Pope, who first carried out the resolution (1899), mentioned in his articles that salts have features for conglomerate formation but nowhere did he note the registration of optical activity and manual sorting of left- and right-handed single crystals. We reinvestigated these salts with the help of X-ray diffraction and found that the space groups of both of them are P2(1)2(1)2(1). However, despite the chiral space group, the enantiomeric composition of the majority of the crystals obtained by crystallization from solutions of racemates was found to be near racemic. Such crystal growth behavior, called lamellar twinning between enantiomers, represents a serious obstacle to the methods of enantiomeric resolution by straightforward crystallization that are used in the chiral industry. The phenomenon probably results from a high concentration in solution of heterochiral growth clusters, which promote the formation of the intergrowth region of twins. To glance experimentally at what might possibly be the first crystal growth units, electrospray ionization FT-ICR mass spectrometry was applied. We were able to register polyionic clusters containing up to five chiral cations. The relative stability of the simplest dimeric clusters (two cations linked by an anion) of 1 with homo- and heterochiral composition was estimated with a B3LYP/SDD calculation, and heterochiral one was found to be more stable by 0.883 kcal/mol.