7-碘吲哚-3-甲醛 | 123020-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 7-碘吲哚-3-甲醛
• 英文名称: 7-Iodo-1H-indole-3-carbaldehyde
• CAS: 123020-22-4
• 化学式: C₉H₆INO
• 分子量: 271.057
• InChiKey: WHGDHUAKWNEPJU-UHFFFAOYSA-N

物化性质

• 熔点：
  111-115°C
• 沸点：
  417.6±25.0 °C(Predicted)
• 密度：
  1.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  7-碘吲哚-3-甲醛 在 sodium cyanide 、 manganese(IV) oxide 、 异丙基氯化镁 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium hexamethyldisilazane 作用下， 生成 methyl 7-[1-[(2-methylpropan-2-yl)oxycarbonyl]-3-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxo-3-phenylmethoxyprop-1-enyl]indol-4-yl]-1-(2-phenylmethoxybenzoyl)indole-3-carboxylate
  参考文献：
  名称：

  Diazonamide Synthesis Studies:  Use of Negishi Coupling to Fashion Diazonamide-Related Biaryls with Defined Axial Chirality

  摘要：

  [GRAPHICS]The syntheses of a bis indole and an indole salicylate with the required axial chirality for diazonamide A are reported. Atropselectivity in these biaryl systems is enforced by an sp(3) stereogenic center in a lactone tether in both cases.

  DOI：

  10.1021/ol026694t
• 作为产物：
  描述：

  7-碘吲哚 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 生成 7-碘吲哚-3-甲醛
  参考文献：
  名称：

  Diazonamide Synthesis Studies:  Use of Negishi Coupling to Fashion Diazonamide-Related Biaryls with Defined Axial Chirality

  摘要：

  [GRAPHICS]The syntheses of a bis indole and an indole salicylate with the required axial chirality for diazonamide A are reported. Atropselectivity in these biaryl systems is enforced by an sp(3) stereogenic center in a lactone tether in both cases.

  DOI：

  10.1021/ol026694t

文献信息

• Expanding the ‘aplysinospin cascade’ through DNA-templated [2+2] photocycloaddition
  作者：Samuel Oger、Nicolas Duchemin、Yara Mayssa Bendiab、Nicolas Birlirakis、Adam Skiredj、Somia Rharrabti、Jean-Christophe Jullian、Erwan Poupon、Michael Smietana、Stellios Arseniyadis、Laurent Evanno

  DOI：10.1039/d3cc00673e

  日期：——

  We report here a general and scalable method for the synthesis of cyclobutane-containing natural products and analogues thereof via a DNA-templated [2+2] photo-induced homo- and heterodimerization of aplysinopsins.

  我们在此报告了一种通用的、可扩展的方法，该方法通过 DNA 引发的 aplysinopsins 的[2+2]光诱导同源和异源二聚化，合成含环丁烷的天然产物及其类似物。
• Modular Access to Diverse Bridged Indole Alkaloid Mimics via a Gold-Triggered Cascade Dearomative Spirocarbocyclization/[4 + 2] Cycloaddition Sequence
  作者：Yi He、Zhen Liu、Danjun Wu、Zhenghua Li、Koen Robeyns、Luc Van Meervelt、Erik V. Van der Eycken

  DOI：10.1021/acs.orglett.9b01296

  日期：2019.6.21

  A modular and streamlined synthetic strategy for the generation of bridged indole alkaloid-like heterocycles from easily available building blocks is elaborated. This approach utilizes an Ugi four-component reaction, establishing diversity, followed by an efficient cationic gold-triggered intramolecular cascade non-oxidative dearomative spirocarbocyclization/concerted [4 + 2] cyclization cascade, furnishing these architecturally complex and distinct bridged heterocyclic scaffolds with good diastereoselectivity.
• SOMEHI, MASANORI;OTA, TOSIXARU;TAXIRA, XIROKO;YAMATO, JOSINORI
  作者：SOMEHI, MASANORI、OTA, TOSIXARU、TAXIRA, XIROKO、YAMATO, JOSINORI

  DOI：——

  日期：——
• Diazonamide Synthesis Studies:  Use of Negishi Coupling to Fashion Diazonamide-Related Biaryls with Defined Axial Chirality
  作者：Ken S. Feldman、Kyle J. Eastman、Guillaume Lessene

  DOI：10.1021/ol026694t

  日期：2002.10.1

  [GRAPHICS]The syntheses of a bis indole and an indole salicylate with the required axial chirality for diazonamide A are reported. Atropselectivity in these biaryl systems is enforced by an sp(3) stereogenic center in a lactone tether in both cases.