N-(2-chlorobenzylidene)methanamine | 17972-08-6

• 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: N-(2-chlorobenzylidene)methanamine
• 英文别名: Methanamine, N-[(2-chlorophenyl)methylene]-；1-(2-chlorophenyl)-N-methylmethanimine
• CAS: 17972-08-6
• 化学式: C₈H₈ClN
• 分子量: 153.611
• InChiKey: XWDRVQQSNBMADV-UHFFFAOYSA-N

物化性质

• 熔点：
  7°C
• 沸点：
  252.49°C (rough estimate)
• 密度：
  1.1558 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-chlorobenzylidene)methanamine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以100%的产率得到N-甲基-2-氯苄胺
  参考文献：
  名称：

  Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[ω-(benzylmethylamino)alkoxy]xanthen-9-ones

  摘要：

  In this work, we further investigated a previously introduced class of cholinesterase inhibitors. The removal of the carbarnic function from the lead compound xanthostigmine led to a reversible cholinesterase inhibitors 3. Some new 3-[omega-(benzylmethylamino)alkoxy]xanthen-9-one analogs were designed, synthesized, and evaluated for their inhibitory activity against both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The length of the alkoxy chain of compound 3 was increased and different substituents were introduced. From the IC50 values, it clearly appears that the carbamic residue is crucial to obtain highly potent AChE inhibitors. On the other hand, peculiarity of these compounds is the high selectivity toward BuChE with respect to AChE, being compound 12 the most selective one (6000-fold). The development of selective BuChE inhibitors may be of great interest to clarify the physiological role of this enzyme and to provide novel therapeutics for various diseases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.026
• 作为产物：
  描述：

  N-甲基-2-氯苄胺 在 CoPz(hmdtn)4 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 N-(2-chlorobenzylidene)methanamine
  参考文献：
  名称：

  一种可见光催化不对称仲胺氧化合成亚胺的 方法

  摘要：

  本发明属于化工和制药技术领域，具体涉及一种可见光催化不对称仲胺氧化合成亚胺的方法。以含硫氮杂金属卟啉为可见光催化剂，1,8‑二氮杂二环十一碳‑7‑烯为助剂，氧气为氧化剂，在λ≥420 nm可见光的照射下实现不对称仲胺的催化氧化，高选择性地获得氧化产物亚胺，为亚胺的生产提供一条高效、节能的新途径。

  公开号：

  CN108623494B

文献信息

• Asymmetric Synthesis of Tetrahydropyridines via an Organocatalytic One-Pot Multicomponent Michael/Aza-Henry/Cyclization Triple Domino Reaction
  作者：Marcus Blümel、Pankaj Chauhan、Robert Hahn、Gerhard Raabe、Dieter Enders

  DOI：10.1021/ol503024d

  日期：2014.11.21

  A low loading of a quinine-derived squaramide efficiently catalyzes the triple-domino Michael/aza-Henry/cyclization reaction between 1,3-dicarbonyl compounds, β-nitroolefins, and aldimines to provide tetrahydropyridines bearing three contiguous stereogenic centers in good yields, excellent enantiomeric excesses, and up to high diastereomeric ratios.

  低负载的奎宁衍生的方酰胺有效地催化 1,3-二羰基化合物、β-硝基烯烃和醛亚胺之间的三多米诺 Michael/aza-Henry/环化反应，以良好的收率提供具有三个连续立体中心的四氢吡啶。对映体过量，以及高达高的非对映体比率。
• Expedient preparation of active pharmaceutical ingredient ketamine under sustainable continuous flow conditions
  作者：Victor-Emmanuel H. Kassin、Romaric Gérardy、Thomas Toupy、Diégo Collin、Elena Salvadeo、François Toussaint、Kristof Van Hecke、Jean-Christophe M. Monbaliu

  DOI：10.1039/c9gc00336c

  日期：——

  ketamine. The scalability of the critical hydroxylation step was assessed in a commercial pilot continuous flow reactor. The process can also be adapted for the preparation of ketamine analogs. A thorough computational study on the backbone rearrangement of the cyclopentylphenylketone scaffold under thermal stress rationalizes the experimental selectivity and the various experimental observations reported

  为有效和可持续地制备活性药物成分氯胺酮，提出了一种鲁棒的三步连续流动程序。该程序依靠连续流处理的主要资产，从可商购获得的化学药品开始，在强化条件下使用低毒性试剂和FDA 3类溶剂。该程序具有独特的分子氧羟基化步骤，依靠硼酸三异丙酯的快速胺化以及采用蒙脱土K10作为非均相催化剂的热解法，所有这三个步骤均在乙醇中进行。这三个步骤可以独立运行，也可以串联在一起，从而为氯胺酮的生产提供了紧凑而有效的装置。在商业中试连续流反应器中评估了关键羟基化步骤的可扩展性。该方法也可以适用于氯胺酮类似物的制备。在热应力下对环戊基苯基酮骨架的骨架重排进行的全面计算研究合理化了实验选择性和本文报道的各种实验观察结果。
• Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron
  作者：Mingkang Zhou、Kaidi Li、Dongping Chen、Ronghua Xu、Guangqing Xu、Wenjun Tang

  DOI：10.1021/jacs.0c04558

  日期：2020.6.10

  We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method

  我们在此报告了一种通用、实用且高效的方法，通过手性二硼模板化的亚胺的还原偶联不对称合成各种手性邻二胺。该协议具有高对映选择性和立体特异性、温和的反应条件、简单的操作程序、使用现成的起始材料和广泛的底物范围。该方法表明了启用二硼的 [3,3]-σ 重排的普遍性。
• A Latent Reaction in a Model GFP Chromophore Revealed upon Confinement: Photohydroxylation of <i>ortho</i>-Halo Benzylidene-3-methylimidazolidiones via an Electrocylization Process
  作者：Shampa R. Samanta、José P. Da Silva、Anthony Baldridge、Laren M. Tolbert、V. Ramamurthy

  DOI：10.1021/ol5013058

  日期：2014.6.20

  Excited state behavior of halogen substituted model GFP chromophores was investigated in an acetonitrile solution and in a confined environment provided by an octa acid capsule in water. Of the ortho, meta, and para halogen substituted GFP chromophores only the ortho compounds gave a new product resulting from an unprecedented photosubstitution of halogens by the hydroxyl group. This unusual reaction

  在乙腈溶液中以及在辛酸胶囊在水中提供的密闭环境中，研究了卤素取代的GFP型发色团的激发态行为。在邻位，间位和对位卤素取代的GFP生色团中，仅邻位化合物会产生新产物，这是由于卤素通过羟基空前的光解而产生的。这种不寻常的反应凸显了密闭空间在实现某些无法实现的光反应中的重要性。
• Thiazolidinones Derived from Dynamic Systemic Resolution of Complex Reversible-Reaction Networks
  作者：Yan Zhang、Olof Ramström

  DOI：10.1002/chem.201304690

  日期：2014.3.17

  A complex dynamic system based on a network of multiple reversible reactions has been established. The network was applied to a dynamic systemic resolution protocol based on kinetically controlled lipase‐catalyzed transformations. This resulted in the formation of cyclized products, where two thiazolidinone compounds were efficiently produced from a range of potential transformations.

  建立了一个基于多个可逆反应网络的复杂动态系统。该网络应用于基于动力学控制的脂肪酶催化转化的动态系统分辨率协议。这导致环化产物的形成，其中从一系列潜在的转化中有效地产生了两种噻唑烷酮化合物。

表征谱图