1-o-Iodphenyl-1-pentanol | 182742-43-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-o-Iodphenyl-1-pentanol
• 英文别名: 1-(2-iodophenyl)pentan-1-ol
• CAS: 182742-43-4
• 化学式: C₁₁H₁₅IO
• 分子量: 290.144
• InChiKey: RLQCVKGRXOPCNM-UHFFFAOYSA-N

物化性质

• 沸点：
  328.1±25.0 °C(Predicted)
• 密度：
  1.510±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-o-Iodphenyl-1-pentanol 在 三乙基(硅烷-d) 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 以99%的产率得到
  参考文献：
  名称：

  Platinum and Ruthenium Chloride-Catalyzed Cycloisomerization of 1-Alkyl-2-ethynylbenzenes: Interception of π-Activated Alkynes with a Benzylic C−H Bond

  摘要：

  Air-stable and commercially available alkynophilic metal salts, such as PtCl2, PtCl4, and [RuCl2(CO)(3)](2), catalyze the cycloisomerization of 1-alkyl-2-ethynylbenzenes to produce Substituted indenes even at all ambient temperature. Electrophilically activated alkynes can be intercepted by simple benzylic C-H bonds at primary, secondary, and tertiary carbon centers. Mechanistic studies, such as labeling studies and kinetic isotope and substituent effects, indicate that the cycloisomerization proceeds through the formation of a vinylidene intermediate and turnover-limiting 1,5-shift of benzylic hydrogen.

  DOI：

  10.1021/jo901045g
• 作为产物：
  描述：

  正溴丁烷 、 2-碘苯甲醛 在 magnesium 、 水 、 氯化铵 作用下， 以 乙醚 为溶剂， 以72%的产率得到1-o-Iodphenyl-1-pentanol
  参考文献：
  名称：

  Platinum and Ruthenium Chloride-Catalyzed Cycloisomerization of 1-Alkyl-2-ethynylbenzenes: Interception of π-Activated Alkynes with a Benzylic C−H Bond

  摘要：

  Air-stable and commercially available alkynophilic metal salts, such as PtCl2, PtCl4, and [RuCl2(CO)(3)](2), catalyze the cycloisomerization of 1-alkyl-2-ethynylbenzenes to produce Substituted indenes even at all ambient temperature. Electrophilically activated alkynes can be intercepted by simple benzylic C-H bonds at primary, secondary, and tertiary carbon centers. Mechanistic studies, such as labeling studies and kinetic isotope and substituent effects, indicate that the cycloisomerization proceeds through the formation of a vinylidene intermediate and turnover-limiting 1,5-shift of benzylic hydrogen.

  DOI：

  10.1021/jo901045g

文献信息

• Fused-Ring Formation by an Intramolecular “Cut-and-Sew” Reaction between Cyclobutanones and Alkynes
  作者：Lin Deng、Likun Jin、Guangbin Dong

  DOI：10.1002/anie.201712487

  日期：2018.3.1

  alkynes to construct cyclohexenone‐fused rings is described herein. The challenge arises from the need for selective coupling at the more sterically hindered proximal position, and can be addressed by using an electron‐rich, but less bulky, phosphine ligand. The control experiment and 13C‐labelling study suggest that the reaction may start with cleavage of the less hindered distal C−C bond of cyclobutanones

  本文描述了在环丁酮和炔烃之间进行分子内“切割和缝合”催化转化以构建环己烯酮稠合环的过程。挑战来自在空间上受阻较大的近端位置进行选择性偶联的需求，可以通过使用富含电子但体积较小的膦配体来解决。对照实验和13 C标记研究表明，该反应可能始于裂解环丁烯酮受阻较少的远端C-C键，然后脱羰和CO重新插入以使Rh插入受阻较近的位置开始。
• Regioselective synthesis and evaluation of 3-alkylidene-1, 3-dihydroisobenzofurans as potential antidepressant agents
  作者：C PRAVEEN、C IYYAPPAN、K GIRIJA、K SURESH KUMAR、P T PERUMAL

  DOI：10.1007/s12039-011-0150-z

  日期：2012.3

  3-Alkylidene-1,3-dihydroisobenzofurans exhibited moderate antidepressant activity as evaluated by forced swim and tail suspension test methods. Virtual screening was carried out by docking the designed compounds into the serotonin binding sites of arabinase protein to predict the analogue binding mode of the compounds to the SSRIs.

  3-亚烷基-1,3-二氢异苯并呋喃在强迫游泳和尾悬试验方法的评估中表现出中等程度的抗抑郁活性。通过将设计的化合物与阿拉伯蛋白酶的血清素结合位点对接，进行了虚拟筛选，以预测化合物与 SSRIs 的类似结合模式。
• Gold-catalyzed Bicyclization of Diaryl Alkynes: Synthesis of Polycyclic Fused Indole and Spirooxindole Derivatives
  作者：Ju Cai、Bing Wu、Guangwei Rong、Cheng Zhang、Lihua Qiu、Xinfang Xu

  DOI：10.1021/acs.orglett.8b00939

  日期：2018.5.4

  An unprecedented gold-catalyzed bicyclization reaction of diaryl alkynes has been developed for the synthesis of indoles in good to high yields. Mechanistically, this alkyne bifunctionalization transformation was terminated by a stepwise formal X–H insertion reaction to furnish the corresponding polycyclic-frameworks with structural diversity, and the key intermediate 3H-indole was isolated and characterized

  已经开发了空前的金催化的二芳基炔烃的双环化反应，以高产率到高产率合成吲哚。从机理上讲，这种炔烃双官能化转化过程是通过逐步的正式X–H插入反应终止的，以使相应的多环骨架具有结构多样性，并且首次对关键中间体3 H-吲哚进行了分离和表征。另外，用PCC作为氧化剂对这些产生的四环吲哚进行进一步转化提供了以高收率直接获得螺硫醇的方法。
• Method for assisting in differential diagnosis and treatment of autistic syndromes
  申请人：Repligen Corporation, a Delaware corporation

  公开号：US20040146495A1

  公开（公告）日：2004-07-29

  A novel relationship between pancreatico-biliary secretion and autistic syndrome is disclosed. This relationship enables a novel therapy for the treatment of the symptoms of autistic syndromes, comprising the administration of a therapeutically effective, preferably intravenous, dose of secretin to an individual with autistic syndrome. The relationship further enables a differential diagnosis for autistic syndrome, comprising an analysis of an individual's blood and/or intestinal tissue for the presence of secretin and comparison of the level of secretin to known norms.

  本研究揭示了胰胆分泌与自闭症之间的新型关系。这种关系促成了一种治疗自闭症综合征症状的新疗法，包括向自闭症综合征患者施用治疗有效剂量（最好是静脉注射）的胰泌素。这种关系进一步实现了自闭症综合征的鉴别诊断，包括分析个体血液和/或肠道组织中是否存在泌乳素，并将泌乳素水平与已知标准进行比较。
• Visible-Light-Promoted Selenylation/Cyclization of <i>o</i>-Alkynyl Benzylazides/<i>o</i>-Propargyl Arylazides: Synthesis of Seleno-Substituted Isoquinolines and Quinolines
  作者：Xi-Rui Gong、Shuang-Shuang Sun、Mei-Lin Ren、Qiao-Yan Wu、Yan-Yan Chen、Yan-Li Xu

  DOI：10.1021/acs.joc.4c00247

  日期：2024.3.15