6-氯二氮杂萘 | 78032-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 6-氯二氮杂萘
• 英文名称: 6-chlorophthalazine
• 英文别名: 6-chloro-phthalazine；6-Chlor-phthalazin
• CAS: 78032-07-2
• 化学式: C₈H₅ClN₂
• 分子量: 164.594
• InChiKey: AINDGCOQTNWCCB-UHFFFAOYSA-N

物化性质

• 熔点：
  132 °C
• 沸点：
  364.3±15.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-氯二氮杂萘 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 14.0h， 生成 diethyl 9-chloro-4,4-dicyano-3-phenyl-3,4-dihydro-1H-pyrido[2,1-a]phthalazine-1,1(2H,11bH)-dicarboxylate
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed [3 + 3] Cycloaddition of Cyclopropane 1,1-Diesters with Phthalazinium Dicyanomethanides

  摘要：

  The Sc(OTf)(3)-catalyzed diastereoselective [3 + 3] cycloaddition of phthalazinium dicyanomethanides with cyclopropane 1,1-diesters proceeded smoothly under mild reaction conditions, affording a variety of 3,4-dihydro-1H-pyrido[2,1-a]phthalazine derivatives in up to 99% yields with excellent diastereoselectivities.

  DOI：

  10.1021/acs.orglett.5b02003
• 作为产物：
  描述：

  4-氯苯甲醛 在 正丁基锂 、 Lithium N-(N,N-dimethyl-2-aminoethyl)-N-methylamide 、 N,N-二甲基甲酰胺 、 氯化铵 、 一水合肼 作用下， 以 正己烷 、 四氢呋喃 、 水 为溶剂， 反应 18.67h， 生成 6-氯二氮杂萘
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed [3 + 3] Cycloaddition of Cyclopropane 1,1-Diesters with Phthalazinium Dicyanomethanides

  摘要：

  The Sc(OTf)(3)-catalyzed diastereoselective [3 + 3] cycloaddition of phthalazinium dicyanomethanides with cyclopropane 1,1-diesters proceeded smoothly under mild reaction conditions, affording a variety of 3,4-dihydro-1H-pyrido[2,1-a]phthalazine derivatives in up to 99% yields with excellent diastereoselectivities.

  DOI：

  10.1021/acs.orglett.5b02003

文献信息

• Phthalazine derivatives from aromatic aldazines
  作者：Stefan K. Robev

  DOI：10.1016/0040-4039(81)80093-7

  日期：1981.1

  A Lewis acid mediated synthesis of phthalazine derivatives II and III from aromatic aldazines I is reported.

  报道了路易斯酸介导的由芳族醛嗪I合成邻苯二嗪衍生物II和III的过程。
• One-Pot Synthesis of Phthalazines and Pyridazino-aromatics: A Novel Strategy for Substituted Naphthalenes
  作者：Simon N. Kessler、Hermann A. Wegner

  DOI：10.1021/ol301167q

  日期：2012.7.6

  desired 1,2-diazine in good to excellent yields. The products have been applied to the bidentate Lewis acid catalyzed inverse electron-demand Diels–Alder (IEDDA) reaction opening a novel two-step entry into substituted naphthalenes, such as Naproxen.

  已经开发了一种新的一锅策略，从芳族醛开始合成酞嗪和哒嗪基-芳族化合物。容许从吸电子到供电子的各种取代基以良好或优异的产率提供所需的1,2-二嗪。该产品已应用于双齿路易斯酸催化的逆电子需求Diels–Alder（IEDDA）反应，开启了新型两步进入取代萘（如萘普生）的过程。
• Combining Bidentate Lewis Acid Catalysis and Photochemistry: Formal Insertion of <i>o</i>-Xylene into an Enamine Double Bond
  作者：Sebastian Ahles、Julia Ruhl、Marcel A. Strauss、Hermann A. Wegner

  DOI：10.1021/acs.orglett.9b01020

  日期：2019.6.7

  A bidentate Lewis acid catalyzed domino inverse-electron-demand Diels–Alder reaction combined with a photoinduced ring opening formally inserts o-xylene moieties into enamine double bonds. After reduction, phenethylamines were obtained in good yields. The scope of the reaction was determined by variation of all three starting compounds: phthalazines, aldehydes, and amines.

  双齿路易斯酸催化的多米诺骨牌逆电子需求的Diels-Alder反应与光致开环的结合将邻二甲苯基团正式插入烯胺双键中。还原后，以良好的产率获得了苯乙胺。通过改变所有三种起始化合物：酞嗪，醛和胺来确定反应范围。
• An Amine Group Transfer Reaction Driven by Aromaticity
  作者：Sebastian Ahles、Silas Götz、Luca Schweighauser、Mirko Brodsky、Simon N. Kessler、Andreas H. Heindl、Hermann A. Wegner

  DOI：10.1021/acs.orglett.8b02967

  日期：2018.11.16

  domino inverse electron-demand Diels–Alder/amine group transfer reaction catalyzed by a bidentate Lewis acid provides 1-amino-1,2-dihydronaphthalenes, a core structure in many bioactive compounds. A concerted mechanism is proposed based on experimental studies as well as DFT computations demonstrating a new general reactivity scheme. The broad scope of the reaction was evaluated by variation of all three

  双齿路易斯酸催化的立体选择性多米诺逆电子需求的Diels-Alder /胺基转移反应提供了1-氨基-1,2-二氢萘，这是许多生物活性化合物的核心结构。基于实验研究和DFT计算，提出了一种协调的机制，该机制证明了一种新的通用反应性方案。通过改变所有三种起始化合物，酞嗪，醛和胺来评估反应的广泛范围。通过克规模的反应证明了可伸缩性，而收率却没有降低。
• Synthesis of Medium-Sized Carbocycles via a Bidentate Lewis Acid-Catalyzed Inverse Electron-Demand Diels–Alder Reaction Followed by Photoinduced Ring-Opening
  作者：Julia Ruhl、Sebastian Ahles、Marcel A. Strauss、Christopher M. Leonhardt、Hermann A. Wegner

  DOI：10.1021/acs.orglett.1c00249

  日期：2021.3.19

  The combination of a Lewis acid-catalyzed inverse electron-demand Diels–Alder (IEDDA) reaction with a photoinduced ring-opening (PIRO) reaction in a domino process has been established as an efficient synthetic method to access medium-sized carbocycles. From readily available electron-rich and electron-poor phthalazines and enamines, respectively, as starting materials, various 9- and 11-membered carbocycles

  在多米诺骨牌工艺中，路易斯酸催化的逆电子需求Diels-Alder反应（IEDDA）与光致开环（PIRO）反应的结合已被确立为一种访问中型碳环化合物的有效合成方法。从容易获得的富电子和贫电子的酞嗪和烯胺分别作为起始原料，制备了各种9元和11元碳环。这种多功能的无过渡金属工具对于拓宽生物活性化合物和功能材料的结构空间将具有宝贵的价值。