2-碘-4-甲氧基苯甲醛 | 105469-13-4

• 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-碘-4-甲氧基苯甲醛
• 英文名称: 2-iodo-4-methoxybenzaldehyde
• 英文别名: 2-Iod-4-methoxy-benzaldehyd
• CAS: 105469-13-4
• 化学式: C₈H₇IO₂
• 分子量: 262.047
• InChiKey: HYWMSRPGGMIKKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C
• 沸点：
  331.4±27.0 °C(Predicted)
• 密度：
  1.780±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  2-碘-4-甲氧基苯甲醛 在 硝酸 、 溶剂黄146 作用下， 生成 3-碘-4-硝基茴香醚
  参考文献：
  名称：

  Synthesis and Antiplasmodial Activity of New Indolone N-Oxide Derivatives

  摘要：

  A series of 66 new indolone-N-oxide derivatives was synthesized with three different methods. Compounds were evaluated for in vitro activity against CQ-sensitive (3D7), CQ-resistant (FcB1), and CQ and pyrimethamine cross-resistant (K1) strains of Plasmodium falciparum (P.f.), its well as for cytotoxic concentration (CC50) on MCF7 and KB human tumor Cell lines. Compound 26 (5-methoxy-indolone-N-oxide analogue) had the most potent antiplasmodial activity in vitro (< 3 nM on FcB1 and = 1.7 nM on 3D7) with a very satisfactory selectivity index (CC50 MCF7/IC50 FcB1: 14623; CC50 KB/IC50 3D7: 198823). In in vivo experiments, compound 1 (dioxymethylene derivatives of the indolone-N-oxide) showed the best antiplasmodial activity against Plasmodium berghei, 62% inhibition of the parasitaemia at 30 mg/kg/day.

  DOI：

  10.1021/jm901300d
• 作为产物：
  描述：

  2-iodo-4-methoxy-N,N-dimethylbenzamide 在 二氯二茂锆 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.13h， 以89%的产率得到2-碘-4-甲氧基苯甲醛
  参考文献：
  名称：

  Schwartz试剂的实用原位生成。还原叔胺为醛和加氢锆

  摘要：

  描述了一种新的高效原位实验方案（Cp 2 ZrCl 2 / LiAlH（OBu- t）3），用于产生Schwartz试剂，该试剂为酰胺到醛的还原以及炔烃的区域选择性加氢锆化加碘提供了便利的方法。和烯烃。突出显示的是通过定向邻位金属化（D o M）化学反应生成的苯甲酰胺的化学选择性还原，可合成有价值的1,2,3-取代的苯甲醛。单步三组分过程在非常短的反应时间内进行，显示出极好的官能团相容性，并使用廉价且长期保存的稳定还原剂。

  DOI：

  10.1021/ol403183a

文献信息

• A Direct Transformation of Aryl Aldehydes to Benzyl Iodides Via Reductive Iodination
  作者：Jayaraman Sembian Ruso、Nagappan Rajendiran、Rajendran Senthil Kumaran

  DOI：10.5012/jkcs.2014.58.1.39

  日期：2014.2.20

  A facile transformation of aryl aldehydes to benzyl iodides through one-pot reductive iodination is reported. This protocol displays remarkable functional group tolerance and the title compound was obtained in good to excellent yield.

  报道了一种通过一锅法还原碘化将芳基醛便捷转化为苄基碘的过程。该方案显示出显著的功能基团耐受性，并且目标化合物以良好至优异的产率获得。
• Coupling‐Isomerization‐Cycloisomerization Reaction (CICIR) – An Unexpected and Efficient Domino Approach to Luminescent 2‐(Hydroxymethylene)indenones
  作者：Helya Janatian Ghazvini、Mahsa Armaghan、Christoph Janiak、Saeed Balalaie、Thomas J. J. Müller

  DOI：10.1002/ejoc.201901413

  日期：2019.11.14

  A Pd/Cu‐catalyzed, base mediated domino coupling‐isomerization‐cycloisomerization reaction (CICIR) unexpectedly furnishes tunable emission‐solvatochromic 2‐(hydroxymethylene)indenones in good to excellent yields.

  Pd / Cu催化的碱介导的多米诺偶联-异构化-环异构化反应（CICIR）出人意料地提供了可调谐发射-溶剂变色2-（羟基亚甲基）茚满，其收率非常好。
• Molybdenum(0)-Promoted Carbonylative Cyclization of<i>o</i>-Haloaryl- and β-Haloalkenylimine Derivatives by Oxidative Addition of a Carbon(sp²)Halogen Bond: Preparation of Two Types of γ-Lactams
  作者：Jun Takaya、Kenichiro Sangu、Nobuharu Iwasawa

  DOI：10.1002/anie.200902884

  日期：2009.9.7

  Lovely lactams: Synthetically useful γ‐lactam derivatives have been prepared through the unique title transformation. By utilizing the characteristic property of the molybdenum complex, two kinds of products (both of which have rarely been obtained by reactions catalyzed by late transition metals) were obtained selectively by adjusting the reaction conditions (see scheme).

  可爱的内酰胺：通过独特的标题转换已制备出可用于合成的γ-内酰胺衍生物。通过利用钼配合物的特性，通过调节反应条件有选择地获得了两种产物（两种产物很少通过后期过渡金属催化的反应获得）。
• Schwartz Reagents: Methods of In Situ Generation and Use
  申请人：Zhao Yigang

  公开号：US20100145060A1

  公开（公告）日：2010-06-10

  Embodiments of the invention provide a method of using Schwartz Reagent, Cp 2 Zr(H)Cl, without accumulating or isolating it. Methods provide mixtures of Cp 2 ZrCl 2 , reductants that selectively reduce Cp 2 ZrCl 2 , and substrates. After reaction of Cp 2 ZrCl 2 and the reductant, an intermediate reduction product is formed, apparently Schwartz Reagent. The in situ Schwartz Reagent then selectively reduces certain functional groups on the substrate. Substrates include tertiary amides, tertiary benzamides, aryl O-carbamates, and heteroaryl N-carbamates, which are reduced to aldehydes, benzaldehydes, aromatic alcohols, and heteroaromatics, respectively. Compared to prior methods, reagents are inexpensive and stable, reaction times are short, and reaction temperature in certain cases is conveniently room temperature. It has been estimated that using the in situ method described herein instead of synthesized or commercially obtained Schwartz Reagent provides a 50% reduction in cost.

  本发明的实施例提供了一种使用Schwartz试剂，Cp2Zr（H）Cl的方法，而无需积累或隔离它。方法提供了Cp2ZrCl2的混合物，选择性还原Cp2ZrCl2的还原剂，以及底物。在Cp2ZrCl2和还原剂发生反应后，形成了一个中间还原产物，显然是Schwartz试剂。然后，原位的Schwartz试剂选择性地还原底物上的某些官能团。底物包括三级酰胺、三级苯酰胺、芳基O-氨基甲酸酯和杂环N-氨基甲酸酯，它们分别被还原为醛、苯甲醛、芳香醇和杂环化合物。与先前的方法相比，试剂价格低廉且稳定，反应时间短，某些情况下的反应温度方便地为室温。据估计，使用本文描述的原位方法而不是合成或商业获得的Schwartz试剂可使成本降低50%。
• Galanthamine Chemistry. V. Formation of Hydroxyapogalanthamine from Galanthaminone and the Synthesis of its Trimethyl Ether.
  作者：Junji Koizumi、Shigeru Kobayashi、Shojiro Uyeo

  DOI：10.1248/cpb.12.696

  日期：——

  Treatment of galanthaminone with hydriodic acid gave hydroxyapogalanthamine, the structure of which has been elucidated by degradation to the known diphenic acid (IV). The trimethyl ether of hydroxyapogalanthamine has been synthesized by two methods, confirming the structure of this important transformation product of galanthaminone. Based on this and other chemical evidence it has been concluded that galanthamine is represented by formula (III).

  用氢碘酸处理过时的加兰他敏，得到了羟基阿波加兰他敏，其结构通过降解已知的二苯酸（IV）得到阐明。羟基阿波加兰他敏的三甲基醚已经通过两种方法合成，确认了这一重要的加兰他敏转化产物的结构。基于此及其他化学证据，得出的结论是，加兰他敏的结构可表示为公式（III）。

表征谱图