2-sec-butyliodobenzene | 1109274-15-8

• 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: 2-sec-butyliodobenzene
• 英文别名: 1-(Sec-butyl)-2-iodobenzene；1-butan-2-yl-2-iodobenzene
• CAS: 1109274-15-8
• 化学式: C₁₀H₁₃I
• 分子量: 260.118
• InChiKey: GOMMGYDPASQOPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-sec-butyliodobenzene 、 2-溴苄醇 在 降冰片烯 、 palladium diacetate 、 cesium pivalate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以93%的产率得到3’-sec-butyl-[1,1’]-biphenyl-2-carbaldehyde
  参考文献：
  名称：

  Formation of a carbonyl group ortho to a biaryl structure or a 6H-dibenzopyran by a palladium/norbornene-catalyzed ordered reaction sequence

  摘要：

  Developments are reported in the catalytic synthesis of biaryls containing an ortho-carbaldehyde or 6H-dibenzopyrans in the presence of palladium/norbornene as catalyst. The reaction of o-substituted aryl iodides and o-bromobenzyl alcohols proceeds by unsymmetrical aryl-aryl coupling to form a seven-membered oxapalladacycle intermediate, which may undergo an intramolecular redox process to form carbonyl groups or a C-O coupling to six-membered cyclic ethers. The predominant formation of di-benzopyrans as well as of biaryl structures containing the oxidized CHO group in one ring and the reduced CH2OH in the other is described along with some mechanistic insights. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.110

文献信息

• Catalytic Dehydrogenation of<i>o</i>-Alkylated or<i>o</i>-Alkoxylated Iodoarenes with Concomitant Hydrogenolysis
  作者：Elena Motti、Marta Catellani

  DOI：10.1002/adsc.200700562

  日期：2008.3.7

  Palladium-catalyzed dehydrogenation of suitable chains bonded to an ortho position of an iodoarene has been achieved by two methods both involving oxidative addition of the iodoarene to palladium(0) and palladacycle formation under mild conditions.

  已通过两种方法实现了键合到碘芳烃邻位的合适链的钯催化脱氢，这两种方法均涉及将碘芳烃氧化加成至钯（0）和在温和条件下形成钯环。
• One-Pot Palladium-Catalyzed Synthesis of Selectively Substituted Phenanthridines by Sequential Aryl-Aryl and Heck Couplings, Aza-Michael and Retro-Mannich Reactions
  作者：Nicola Della Ca'、Elena Motti、Antonio Mega、Marta Catellani

  DOI：10.1002/adsc.201000114

  日期：——

  A catalytic synthesis of selectively substituted phenanthridines is achieved through a reaction sequence involving palladium/norbornene‐catalyzed unsymmetrical aryl‐aryl and Heck couplings followed by aza‐Michael and retro‐Mannich reactions. In spite of the many steps involved the method is very simple and allows the formation of selectively substituted phenanthridines under mild conditions in a straightforward

  通过涉及钯/降冰片烯催化的不对称芳基-芳基和Heck偶联的反应序列，然后进行氮杂-迈克尔和逆曼尼希反应，可实现选择性取代的菲啶的催化合成。尽管涉及许多步骤，但该方法非常简单，并允许在温和条件下以简单易用的一锅反应从容易获得的芳基碘化物和溴化物开始形成选择性取代的菲啶。
• A catalytic synthesis of selectively substituted biaryls through sequential intermolecular coupling involving arene and ketone C–H bond functionalization
  作者：Giovanni Maestri、Nicola Della Ca’、Marta Catellani

  DOI：10.1039/b909207b

  日期：——

  Selectively substituted biaryls containing a ketone unit are obtained under mild conditions in satisfactory yields by a simple reaction of ortho-substituted aryl iodides and ketones in the presence of palladium and norbornene as catalysts.

  在钯和降冰片烯作为催化剂的存在下，通过邻位取代的芳基碘化物和酮的简单反应，可以在温和的条件下以令人满意的产率获得含有酮单元的选择性取代的联芳基。
• LIGANDS FOR METALS AS CATALYSTS FOR CARBON-CARBON BOND FORMATION
  申请人：LIANG Lan-Chang

  公开号：US20090163740A1

  公开（公告）日：2009-06-25

  The present invention provides a family of novel and stable ligands which chelate with a metal to form a complex. The ligand contains a t-butyl group or a ring, particularly a substituted aromatic group, linked to a nitrogen atom. The nitrogen atom further links to PR 1 R 2 , PR 1 R 2 R 9 , P(═O)R 1 R 2 , NR 1 R 2 , OR 1 , SR 1 , or AsR 1 R 2 group with a saturated or unsaturated hydrocarbon such that the structure of the ligand can be stabilized.

  本发明提供了一系列新颖且稳定的配体，这些配体与金属螯合形成复合物。该配体含有t-丁基基团或环，特别是取代芳基团，与氮原子连接。氮原子进一步与PR1R2、PR1R2R9、P(═O)R1R2、NR1R2、OR1、SR1或AsR1R2基团链接，带有饱和或不饱和的碳氢化合物，从而使配体的结构得以稳定。
• Method for producing an aromatic compound having an alkyl group with at least three carbon atoms
  申请人：TORAY INDUSTRIES, INC.

  公开号：EP0985649A2

  公开（公告）日：2000-03-15

  Aromatic compounds having an alkyl group with at least 3 carbon atoms are produced in a process comprising at least one of the following steps: (1) a step of contacting a starting material that contains an aromatic compound having a branched alkyl group with at least 3 carbon atoms, with a zeolite-containing catalyst in a liquid phase in the presence of hydrogen therein, thereby changing the position of the carbon atoms of the alkyl group bonding to the aromatic ring of the compound; (2) a step of contacting a starting material that contains an aromatic compound having a branched alkyl group with at least 3 carbon atoms, with a catalyst containing zeolite and containing rhenium and/or silver, in a liquid phase, thereby changing the position of the carbon atoms of the alkyl group bonding to the aromatic ring of the compound; (3) a step of contacting a halogenated aromatic compound having an alkyl group with at least 3 carbon atoms, with an acid-type catalyst, thereby isomerizing the compound; and (4) a step of treating a mixture of isomers of an aromatic compound having an alkyl group with at least 3 carbon atoms, with a zeolite adsorbent that contains at least one exchangable cation selected from alkali metals, alkaline earth metals, lead, thallium and silver, thereby separating a specific isomer from the isomer mixture through adsorption.

  具有至少 3 个碳原子烷基的芳香族化合物的生产工艺至少包括以下一个步骤： (1) 将含有至少 3 个碳原子的支链烷基的芳香族化合物的起始原料在液相中与含沸石的催化剂在氢存在的情况下接触，从而改变烷基的碳原子与化合物的芳香环键合的位置； (2) 将含有芳香族化合物的起始原料与含沸石和含铼和/或银的催化剂在液相中接触，该芳香族化合物具有至少 3 个碳原子的支链烷基，从而改变烷基碳原子与化合物芳香环键合的位置； (3) 将具有至少 3 个碳原子的烷基的卤代芳香族化合物与酸型催化剂接触，从而使该化合物异构化；以及 (4) 用沸石吸附剂处理具有至少 3 个碳原子的烷基的芳香族化合物的异构体混合物，该沸石吸附剂含有至少一种选自碱金属、碱土金属、铅、铊和银的可交换阳离子，从而通过吸附从异构体混合物中分离出特定的异构体。