1-(2-iodobenzyl)indole-2-carbaldehyde | 155912-06-4

• 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
• 英文名称: 1-(2-iodobenzyl)indole-2-carbaldehyde
• 英文别名: 1-[(2-Iodophenyl)methyl]indole-2-carbaldehyde
• CAS: 155912-06-4
• 化学式: C₁₆H₁₂INO
• 分子量: 361.182
• InChiKey: FWQRJFPTJATEQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-iodobenzyl)indole-2-carbaldehyde 在 palladium diacetate 、 氢氧化钾 、 thallium(I) acetate 、 三苯基膦 作用下， 以 乙腈 为溶剂， 生成 11-(ethoxycarbonylmethylidene)-6H-indolo<1,2-b>isoquinoline
  参考文献：
  名称：

  Germain, Andrew L.; Gilchrist, Thomas L.; Kemmitt, Paul D., Heterocycles, 1994, vol. 37, # 2, p. 697 - 700

  摘要：

  DOI：
• 作为产物：
  描述：

  1H-吲哚-2-甲醛 、 邻碘氯苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以82%的产率得到1-(2-iodobenzyl)indole-2-carbaldehyde
  参考文献：
  名称：

  Morita–Baylis–Hillman reaction of indole-2-carboxaldehyde: new vistas for indole-annulated systems

  摘要：

  DABCO-mediated Morita-Baylis-Hillman reactions of several 1-substituted-indole-2-carboxaldehydes are disclosed. It was discovered that carboethoxy or tert-butoxycarbonyl groups installed at N-1 undergo cleavage under the reaction conditions to afford 2-substituted indoles. Utility of the N-substituted adducts for preparing a variety of annulated indoles has been exemplified. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.078

文献信息

• Altering the Cyclization Modes: Temperature-Dependent Intramolecular 7-<i>Endo-Dig</i> vs 6-<i>Endo-Dig</i> Electrophilic Ring Closures
  作者：Maloy Nayak、Young Kee Kang、Ikyon Kim

  DOI：10.1021/acs.orglett.7b00472

  日期：2017.3.17

  intramolecular alkyne carbonyl metathesis, two distinctive modes of cyclization were revealed to depend on the reaction temperatures. 5H-Benzo[e]pyrrolo[1,2-a]azepine-1-carbaldehydes with a substituent at the C11 position were obtained as major products at 90 °C as a result of intramolecular 7-endo-dig cyclization, while 6-endo-dig ring closure by electrophilic addition of nitrogen of the pyrrole to a

  在尝试通过酸催化的分子内炔烃羰基复分解反应构建10-酰基-5 H-苯并[ e ]吡咯并[1,2- a ]氮杂环庚烷时，发现两种独特的环化方式取决于反应温度。5 ħ -苯并[ ë ]吡咯并[1,2一]获得具有在C11位置的取代基氮杂-1- carbaldehydes作为主要产物在90℃下为分子内7-结果内切挖环化，而6 -内挖在某些情况下，在40°C时观察到在酸性介质下亲电将吡咯的氮加成至乙烯基阳离子上，然后进行空前的多米诺骨牌重排过程，从而导致闭环，从而生成5-芳基-11 H-苯并[ d ]吡咯并[ 1,2- a ]氮杂-1-甲醛与以前的产品。
• Germain, Andrew L.; Gilchrist, Thomas L.; Kemmitt, Paul D., Heterocycles, 1994, vol. 37, # 2, p. 697 - 700
  作者：Germain, Andrew L.、Gilchrist, Thomas L.、Kemmitt, Paul D.

  DOI：——

  日期：——
• 1—Azatriene cyclisation as a route to annelated pyrido[4,3- b ]indoles
  作者：Thomas L. Gilchrist、Paul D. Kemmitt、Andrew L. Germain

  DOI：10.1016/s0040-4020(97)00117-8

  日期：1997.3

  Derivatives of indole-3-carbaldehyde oxime have been prepared that bear a carbon-carbon double bond at C-2 and a five- or six-membered ring linking the alpha-carbon artom of the vinyl group and the indole nitrogen atom. Compound 9, with a five-membered ring linking the two atoms, failed to undergo a cyclisation reaction on heating. However the oximes 16 and 22, with a six-memberd ring linking the two atoms. cyclised in boiling toluene. The cyclisation led to the formation of the pyrido-indoles 17 and 18, respectively. (C) 1997 Elsevier Science Ltd.
• Morita–Baylis–Hillman reaction of indole-2-carboxaldehyde: new vistas for indole-annulated systems
  作者：Subhasish Biswas、Virender Singh、Sanjay Batra

  DOI：10.1016/j.tet.2010.07.078

  日期：2010.9

  DABCO-mediated Morita-Baylis-Hillman reactions of several 1-substituted-indole-2-carboxaldehydes are disclosed. It was discovered that carboethoxy or tert-butoxycarbonyl groups installed at N-1 undergo cleavage under the reaction conditions to afford 2-substituted indoles. Utility of the N-substituted adducts for preparing a variety of annulated indoles has been exemplified. (C) 2010 Elsevier Ltd. All rights reserved.