4-(chloromethyl)-N-methyl-2-nitrobenzenamine | 130597-56-7

• 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: 4-(chloromethyl)-N-methyl-2-nitrobenzenamine
• 英文别名: N-methyl-4-chloromethyl-2-nitroaniline；4-methylamino-3-nitrobenzyl chloride；4-(chloromethyl)-N-methyl-2-nitroaniline
• CAS: 130597-56-7
• 化学式: C₈H₉ClN₂O₂
• 分子量: 200.625
• InChiKey: VYTKQQBCZAWJMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2921430090

反应信息

• 作为反应物：
  描述：

  4-(chloromethyl)-N-methyl-2-nitrobenzenamine 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 31.67h， 生成 2-[(7α-O-10-methyl-7-isoalloxyazinyl)methyl]-α-cyclodextrin
  参考文献：
  名称：

  Artificial redox enzymes. 1. Synthetic strategies

  摘要：

  Organic models of flavoenzymes consist of a binding site covalently attached to a flavin derivative acting as the catalytic site. The earlier reported synthesis of such a model using alpha-cyclodextrin as the binding site proved to be difficult to reproduce with beta-cyclodextrin. The synthetic strategy involved attaching a fully constructed riboflavin onto a cyclodextrin by a nucleophilic reaction. Riboflavin was found to decompose under the reaction conditions. A new method for the synthesis of flavocyclodextrins involving construction of the flavin moiety onto cyclodextrin is convenient and can be used to synthesize 6-flavocyclodextrins and 2-flavocyclodextrins.

  DOI：

  10.1021/jo00027a031
• 作为产物：
  描述：

  4-氯-3-硝基苯甲醛 在 盐酸 、 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 4-(chloromethyl)-N-methyl-2-nitrobenzenamine
  参考文献：
  名称：

  Artificial redox enzymes. 1. Synthetic strategies

  摘要：

  Organic models of flavoenzymes consist of a binding site covalently attached to a flavin derivative acting as the catalytic site. The earlier reported synthesis of such a model using alpha-cyclodextrin as the binding site proved to be difficult to reproduce with beta-cyclodextrin. The synthetic strategy involved attaching a fully constructed riboflavin onto a cyclodextrin by a nucleophilic reaction. Riboflavin was found to decompose under the reaction conditions. A new method for the synthesis of flavocyclodextrins involving construction of the flavin moiety onto cyclodextrin is convenient and can be used to synthesize 6-flavocyclodextrins and 2-flavocyclodextrins.

  DOI：

  10.1021/jo00027a031

文献信息

• Selective modification at the 3-position of β-cyclodextrin
  作者：Shengping Tian、Peter Forgo、Valerian T. D'Souza

  DOI：10.1016/0040-4039(96)01944-2

  日期：1996.11

  Heptakis(6-O-tert-butyldimethylsilyl)β-cyclodextrin reacts with N-methyl-4-chloromethyl-2-nitroaniline to produce the 3-modified cyclodextrin after the necessary deprotection step. Complete NMR assignment and its comparison with cyclodextrin derivatives modified by the same group at the 2- and 6-position is reported.

  Heptakis（6- ø -叔丁基二甲基）β环糊精发生反应与ñ -甲基-4-氯甲基-2-硝基苯胺，以产生必要的脱保护步骤之后的3改性的环糊精。报告了完整的NMR归属及其与在2和6位上被同一基团修饰的环糊精衍生物的比较。
• Selective protection of the secondary side of β-cyclodextrin
  作者：Shengping Tian、Valerian T. D'Souza

  DOI：10.1016/s0040-4039(00)78537-6

  日期：1994.12

  Selective protection of the secondary side of β-cyclodextrin by reaction with t-butyldimethylsilyl chloride in the presence of NaH in dry DMF, is reported. Although, all the hydroxyl groups are not silylated in this reaction, these groups offer steric protection and direct the incoming electrophile to the primary side of the molecule.

  据报道，在干燥的DMF中，在NaH存在下，通过与叔丁基二甲基甲硅烷基氯反应，对β-环糊精的次级侧进行了选择性保护。尽管所有羟基均未在该反应中被甲硅烷基化，但这些基团可提供空间保护，并将进入的亲电子体引导至分子的初级侧。
• Artificial redox enzymes
  申请人：Curators of the University of Missouri

  公开号：US05258370A1

  公开（公告）日：1993-11-02

  Artificial redox enzymes are disclosed wherein one or more redox coenzymes or cofactors are linked to the 2-O, 3-O or 6-O positions of a D-glucopyranose ring of .alpha.-, .beta.-, or .gamma.-cyclodextrins. Also disclosed are facile synthetic methods for producing said artificial redox enzymes in good yield, and methods of use of such compositions.

  公开了一种人工氧化还原酶，其中一个或多个氧化还原辅酶或辅因子与α-、β-或γ-环糊精的2-O、3-O或6-O位置连接。同时还公开了制备该类人工氧化还原酶的简便合成方法，并公开了使用这种组合物的方法。
• Selectively Monomodified Cyclodextrins. Synthetic Strategies
  作者：Shengping Tian、Henghu Zhu、Peter Forgo、Valerian T. D'Souza

  DOI：10.1021/jo991347r

  日期：2000.5.1

  ;Monomodifications of cyclodextrins to give selectively 2-, 3-, or 6-substituted product is a challenging task because of the number of hydroxyl groups that can potentially react with the incoming reagent. The principles and the methods involved in manipulations of the differences in the chemistry of these hydroxyl groups to control the outcome of an electrophilic reaction with them to produce monoalkylated (ether-linkaged) cyclodextrin derivatives are discussed and illustrated.
• A convenient method for functionalization of the 2-position of cyclodextrins
  作者：Ding Rong、Valerian T. D'Souza

  DOI：10.1016/s0040-4039(00)97599-3

  日期：1990.1