2-氯-6-碘苯甲醛 | 51738-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氯-6-碘苯甲醛
• 英文名称: 2-chloro-6-iodobenzaldehyde
• CAS: 51738-07-9
• 化学式: C₇H₄ClIO
• 分子量: 266.466
• InChiKey: NWXVAUFKPOPUAV-UHFFFAOYSA-N

物化性质

• 沸点：
  289.6±25.0 °C(Predicted)
• 密度：
  1.971±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件为2-8°C，避光，并保存在惰性气体中。

反应信息

• 作为反应物：
  描述：

  2-氯-6-碘苯甲醛 在 甲酸 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 3-(2-chloro-6-iodophenyl)-N-methylpropanamide
  参考文献：
  名称：

  Palladium-Catalyzed, Norbornene-Mediated, ortho-Amination ipso-Amidation: Sequential C–N Bond Formation

  摘要：

  A palladium-catalyzed, norbornene-mediated ortho- and ipso-C-N bond-forming Catellani reaction is reported. This reaction proceeds through a sequential intermolecular amination followed by intramolecular cyclization of a tethered amide. The products, ortho-aminated dihydroquinolinones, were generated in moderate to good yields and, are present in bioactive, molecules. This work highlights the challenge Of competing intra-vs intermolecular palladium-catalyzed processes.

  DOI：

  10.1021/acs.orglett.7b03577
• 作为产物：
  描述：

  2-氨基-6-氯苯甲酸 在 盐酸 、 重铬酸吡啶 、 硼酸三甲酯 、 dimethyl sulfide borane 、 silica gel 、 sodium nitrite 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 14.0h， 生成 2-氯-6-碘苯甲醛
  参考文献：
  名称：

  Palladium-Catalyzed, Norbornene-Mediated, ortho-Amination ipso-Amidation: Sequential C–N Bond Formation

  摘要：

  A palladium-catalyzed, norbornene-mediated ortho- and ipso-C-N bond-forming Catellani reaction is reported. This reaction proceeds through a sequential intermolecular amination followed by intramolecular cyclization of a tethered amide. The products, ortho-aminated dihydroquinolinones, were generated in moderate to good yields and, are present in bioactive, molecules. This work highlights the challenge Of competing intra-vs intermolecular palladium-catalyzed processes.

  DOI：

  10.1021/acs.orglett.7b03577

文献信息

• Mild, Efficient, and Highly Regioselective Synthesis of 2,6-Diiodobenzaldehyde Derivatives
  作者：Raed M. Al-Zoubi、Khaled T. Jaradat、Walid K. Al-Jammal、Robert McDonald

  DOI：10.1055/s-0040-1708004

  日期：2020.6

  via highly regioselective metal–iodine exchange (MIE) of 5-substituted 1,2,3-triiodobenzenes is reported. The nature of substituents (R) on the phenyl has a large influence on the reactivity of reaction but not on the regioselectivity. The regioselectivity of the MIE can be controlled by the use of ethyl formate as a formylating agent providing only the internal benzaldehyde derivatives in excellent

  报道了通过 5-取代的 1,2,3-三碘苯的高区域选择性金属碘交换 (MIE) 高效且通用的合成 2,6-二碘苯甲醛。苯基上的取代基 (R) 的性质对反应的反应性有很大影响，但对区域选择性没有影响。MIE 的区域选择性可以通过使用甲酸乙酯作为甲酰化剂来控制，仅提供具有优异位点选择性的内部苯甲醛衍生物。最好的反应性和最高的分离产率是由带有富电子取代基的产品提供的。还证明了目标化合物作为合成中有价值的前体的几种化学转化，以良好的分离产率提供了所需的衍生物。本报告公开了合成 2 的方案，
• Brønsted-Acid-Catalyzed Synthesis of 3-Alkoxy and 3-Sulfamido Indanones via a Tandem Cyclization
  作者：Ni-Ni Zhou、Si-Si Ning、Xiao-Juan Tong、Ting-Ting Luo、Jin Yang、Lin-Qiang Li、Ming-Jin Fan、De-Suo Yang、Hai-Tao Zhu

  DOI：10.1021/acs.joc.9b00791

  日期：2019.7.5

  Brønsted-acid-catalyzed allylic substitution reactions of the in situ generated 3-hydroxy indanones with alcohols and sulfamides were investigated, which provided a facile route for the synthesis of a large variety of 3-alkoxy and 3-sulfamido indanones. The key intermediates, 3-hydroxy indanones, were obtained through the intramolecular Meyer–Schuster rearrangement of o-propargyl alcohol benzaldehydes. The resulting

  研究了布朗斯台德酸催化的原位生成的3-羟基茚满酮与醇和磺酰胺的烯丙基取代反应，这为合成大量的3-烷氧基和3-磺酰胺基茚满酮提供了便捷的途径。关键中间体3-羟基茚满酮是通过邻炔丙基醇苯甲醛的Meyer-Schuster分子内重排获得的。可以通过烯丙基磺酰胺化和还原反应选择性地修饰所得的3-苄氧基茚满酮。
• Method for the treatment of CNS disorders with substituted 2-imidazoles or imidazole derivatives
  申请人：Galley Guido

  公开号：US20070197621A1

  公开（公告）日：2007-08-23

  The present invention relates a method for treating depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders which comprises administering to an individual a therapeutically effective amount of a compound of formula I wherein R, R 1 , R 2 , A and n are as defined in the specification and to their pharmaceutically active salts. The invention also relates to novel compounds of formula I, pharmaceutical compositions containing them, and methods for their preparation.

  本发明涉及一种治疗抑郁症、焦虑症、双相情感障碍、注意力缺陷多动障碍、压力相关障碍、精神分裂症等精神障碍、帕金森病等神经系统疾病、阿尔茨海默病等神经退行性疾病、癫痫、偏头痛、高血压、物质滥用、进食障碍、糖尿病、糖尿病并发症、肥胖症、血脂异常、能量消耗和吸收障碍、体温稳态障碍、睡眠和昼夜节律障碍以及心血管疾病的方法，包括向个体施用化合物I的治疗有效量，其中R、R1、R2、A和n如规范中所定义，以及其药用活性盐。该发明还涉及化合物I的新颖化合物、含有它们的药物组合物以及它们的制备方法。
• Monodentate Transient Directing Group-Assisted Palladium-Catalyzed Direct <i>ortho</i>-C–H Iodination of Benzaldehydes for Total Synthesis of Hernandial
  作者：Ming La、Dandan Liu、Xuerong Chen、Fang-Lin Zhang、Yirong Zhou

  DOI：10.1021/acs.orglett.1c03491

  日期：2021.12.3

  as the optimal monodentate transient directing group (MonoTDG). Moderate to excellent yields and good selectivity were achieved for a broad substrate scope under mild conditions. More importantly, the synthetic application was demonstrated by a concise two-step total synthesis of the natural product hernandial, which was accomplished by merging this new MonoTDG-assisted C–H iodination and subsequent

  在市售的 2,5-双(三氟甲基)苯胺作为最佳单齿瞬态导向基团 (MonoTDG) 的帮助下，成功开发了第一个钯催化的苯甲醛直接o -C-H 碘化反应。在温和条件下，对于广泛的底物范围，实现了中等至优异的产率和良好的选择性。更重要的是，合成应用通过天然产物 hernandial 的简明两步全合成得到证明，这是通过合并这种新的 MonoTDG 辅助 C-H 碘化和随后的铜催化交叉偶联来完成的。
• 1,2,3-Triazoles as inhibitors of indoleamine 2,3-dioxygenase 2 (IDO2)
  作者：Ute F. Röhrig、Somi Reddy Majjigapu、Daniela Caldelari、Nahzli Dilek、Patrick Reichenbach、Kelly Ascencao、Melita Irving、George Coukos、Pierre Vogel、Vincent Zoete、Olivier Michielin

  DOI：10.1016/j.bmcl.2016.07.031

  日期：2016.9

  Indoleamine 2,3-dioxygenase 2 (IDO2) is a potential therapeutic target for the treatment of diseases that involve immune escape such as cancer. In contrast to IDO1, only a very limited number of inhibitors have been described for IDO2 due to inherent difficulties in expressing and purifying a functionally active, soluble form of the enzyme. Starting from our previously discovered highly efficient 4-aryl-1

  吲哚胺2，3-二加氧酶2（IDO2）是潜在的治疗靶标，用于治疗涉及免疫逃逸的疾病，例如癌症。与IDO1相比，由于表达和纯化酶的功能活性，可溶形式存在固有的困难，因此仅对IDO2的抑制剂进行了描述。从我们先前发现的高效4-芳基-1,2,3-三唑IDO1抑制剂支架开始，我们使用基于计算结构的方法设计IDO2抑制剂，然后在细胞分析中进行测试。我们的方法产生了IDO2的低分子量抑制剂，IDO2的活性最高，显示出IC 50mIDO2的选择性值为51μM，选择性是hIDO1的两倍。这些化合物可用作研究IDO2生物学作用的分子探针，并可能启发设计新的IDO2抑制剂。