benzylidene dimethyl ammonium chloride | 52853-20-0

• 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: benzylidene dimethyl ammonium chloride
• 英文别名: benzylidene-dimethyl-ammonium chloride；N-benzylidene-N-methylmethanaminium chloride；benzylidenedimethylammonium chloride；N-Benzylidendimethylammonium-chlorid；Methanaminium, N-methyl-N-(phenylmethylene)-, chloride；benzylidene(dimethyl)azanium;chloride
• CAS: 52853-20-0
• 化学式: C₉H₁₂N*Cl
• 分子量: 169.654
• InChiKey: NNUFCPXGFRLSRB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.62
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  benzylidene dimethyl ammonium chloride 在 六甲基磷酰三胺 、 lithium 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到N,N-二甲基苄胺
  参考文献：
  名称：

  Iminopinacol coupling with lithium: electron-transfer mediators

  摘要：

  The addition of tert-butyl borate or ethyl formate to N-alkylbenzalimines directs the reaction pathway from the Birch reduction to the pinacol-type coupling with lithium in THF; an analogous reaction with a dimethylimmonium salt requires a trace titanium catalyst as the electron-transfer mediator.

  DOI：

  10.1070/mc2002v012n06abeh001617
• 作为产物：
  描述：

  N,n,N,N-四甲基-1-苯基甲烷二胺 在 乙酰氯 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以80%的产率得到benzylidene dimethyl ammonium chloride
  参考文献：
  名称：

  芳香醛亚胺衍生物与低价钛试剂还原偶联形成1,2-二芳基乙二胺的应用范围†

  摘要：

  使用低价钛试剂与形成1,2-二芳基乙二胺单元的芳香醛亚胺衍生物进行还原偶联的范围和限制

  DOI：

  10.1002/hlca.19880710818

文献信息

• 3-amin3-arylpropan-1-ol compounds, their preparation and use
  申请人：Gruenenthal GmbH

  公开号：US06410790B1

  公开（公告）日：2002-06-25

  3-amino-3-arylpropan-1-ol compounds of formula I: R1 and R2 independently denoting C1-6 alkyl, or together denoting a (CH2)2-6 ring optionally substituted by phenyl, R3 denoting C3-6 alkyl, C3-6 cycloalkyl, aryl optionally containing heteroatoms and optionally substituted by R6 to R8, or a substituted C1-3 alkylphenyl of formula XII:  R4 and R5 independently denoting C1-6 alkyl, C3-6 cycloalkyl, phenyl, benzyl, or phenethyl, or together forming a (CH2)3-6 or CH2CH2OCH2CH2 ring, R6 to R8 independently denoting H, F, Cl, Br, CHF2, CF3, OH, OCF3, OR14, NR15R16, SR14, phenyl, SO2CH3, SO2CF3, C1-6 alkyl, CN, COOR14, or CONR15R16, or together forming a OCH2O, OCH2CH2O, CH═CHO, CH═C(CH3)O or (CH2)4 ring, R14 denoting C1-6 alkyl, phenyl, benzyl, or phenethyl, R15 and R16 independently denoting H, C1-6 alkyl, phenyl, benzyl or phenethyl, and A denoting optionally substituted aryl optionally containing heteroatoms, or a diastereomer or enantiomer or pharmaceutically acceptable salt thereof, and their preparation and use in pharmaceutical compositions.

  公式I的3-氨基-3-芳基丙醇化合物： R1和R2独立表示C1-6烷基，或一起表示一个(CH2)2-6环，该环可以选择性地被苯基取代， R3表示C3-6烷基，C3-6环烷基，含有杂原子并且可以选择性地被R6至R8取代的芳基，或者是公式XII的取代C1-3烷基苯基： R4和R5独立表示C1-6烷基，C3-6环烷基，苯基，苄基，或苄乙基，或者一起形成一个(CH2)3-6或CH2CH2OCH2CH2环， R6至R8独立表示H，F，Cl，Br，CHF2，CF3，OH，OCF3，OR14，NR15R16，SR14，苯基，SO2CH3，SO2CF3，C1-6烷基，CN，COOR14，或CONR15R16，或者一起形成一个OCH2O，OCH2CH2O，CH═CHO，CH═C(CH3)O或(CH2)4环， R14表示C1-6烷基，苯基，苄基，或苄乙基， R15和R16独立表示H，C1-6烷基，苯基，苄基或苄乙基，以及 A表示可以选择性地被取代的芳基，该芳基可以含有杂原子， 或其对映异构体或对映体或其药学上可接受的盐，以及它们在制备和使用药物组合物中的用途。
• One-pot conversion of aromatic compounds to the corresponding bis(indolyl)methanes by the Vilsmeier–Haack reaction
  作者：Hojat Veisi、Meral Ataee、Pegah Darabi-Tabar、Effat Amiri、Ali Reza Faraji

  DOI：10.1016/j.crci.2013.09.011

  日期：2014.4

  Résumé Various electron-rich aromatics could be smoothly converted into the corresponding bis(indolyl)methanes in good to moderate yields by treatment of electron-rich aromatics with POCl3 and DMF, followed by treatment with indole at room temperature. The present article is the first report on a novel metal-free one-pot method for the preparation of bis(indolyl)methanes from electron-rich aromatics.

  摘要 通过电子丰富的芳香族化合物与POCl3和DMF的处理，随后在室温下与吲哚反应，可以顺利地将多种电子丰富的芳香族化合物转化为相应的二(吲哚基)甲烷，产率良好至中等。本文首次报道了一种新颖的无金属一步法，用于从电子丰富的芳香族化合物制备二(吲哚基)甲烷。
• The Vinylogous Mannich Reaction: An Efficient Access to Substituted Nicotinonitriles
  作者：Nikolaus Risch、Andreas Winter

  DOI：10.1055/s-2003-42044

  日期：——

  A straightforward method for the preparation of substituted nicotinonitriles has been developed. Starting from conjugated β-enaminonitriles and iminium salts, this methodology establishes a convenient access to 6-aryl- (5), 6-amino- (16) and 6-carboxylic ester-substituted derivatives 14 and as well to acetic acid-substituted pyrroles 12.

  已开发出一种制备取代烟腈的简单方法。从共轭 β-烯氨基腈和亚胺盐开始，该方法建立了对 6-芳基-(5)、6-氨基-(16) 和 6-羧酸酯取代衍生物 14 以及乙酸取代吡咯的便捷访问12.
• α-(Dimethylamino)amides from a carbamoylsilane and iminium salts
  作者：Jianxin Chen、Robert F. Cunico

  DOI：10.1016/s0040-4039(02)02093-2

  日期：2002.11

  The reaction of a carbamoylsilane with iminium salts derived from aldehydes lacking α-hydrogens affords the title compounds.

  氨基甲酰基硅烷与衍生自缺乏α-氢的醛的亚胺盐的反应得到标题化合物。
• Aminoalkylation of Electron-Rich Aromatic Compounds Using Performed Iminium Salts Derived from Aldehydes other than Formaldehyde
  作者：Hans-Joachim Grumbach、Michael Arend、Nikolaus Risch

  DOI：10.1055/s-1996-4301

  日期：1996.7

  Preformed iminium salts derived from aldehydes other than formaldehyde are demonstrated to be excellent reagents for the aminoalkylation of indoles, phenols and N,N-dimethylaniline. This method provides a simple and straightforward route to a variety of aromatic Mannich bases which are difficult to obtain by other procedures. Surprisingly, the reaction between N-methylindole or 2-naphthol with a preformed N-silyl iminium salt led to the formation of a bisindolylmethane or a dihydrooxazine derivative, respectively.

  预先形成的来自醛类（除了甲醛）的亚氨盐被证明是吲哚、酚和N,N-二甲基苯胺氨基烷基化的优良试剂。这种方法提供了一条简单直接的途径，用于合成多种难以通过其他方法获得的芳香Mannich碱。令人惊讶的是，N-甲基吲哚或2-萘酚与预先形成的N-硅亚氨盐反应分别产生了双吲哚甲烷或二氢吡咯啉衍生物。