2-iodo-N,N-diallylaniline | 73396-92-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-iodo-N,N-diallylaniline
• 英文别名: N,N-diallyl-2-iodoaniline；2-iodo-N,N-bis(prop-2-enyl)aniline
• CAS: 73396-92-6
• 化学式: C₁₂H₁₄IN
• 分子量: 299.154
• InChiKey: RRAUEKKHBBGFQK-UHFFFAOYSA-N

物化性质

• 沸点：
  313.4±42.0 °C(Predicted)
• 密度：
  1.454±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-iodo-N,N-diallylaniline 在 甲基叔丁基醚 、 四甲基乙二胺 、 苯基锂 作用下， 以 乙醚 、 环己烷 、 正戊烷 为溶剂， 反应 1.0h， 以70%的产率得到1-allyl-3-iodomethylindoline
  参考文献：
  名称：

  Catalytic Cycloisomerization of Unsaturated Organoiodides

  摘要：

  Catalytic quantities of phenyllithium (PhLi) have been found to initiate novel 5-exo cycloisomerization of a variety of structurally diverse unsaturated organoiodides. The isomerization reaction appears to be a process of broad synthetic utility for the preparation of iodomethyl-substituted five-membered rings. Primary, secondary, tertiary, or aryl iodides tethered to a suitably positioned carbon-carbon pi-bond are converted cleanly to their cyclic isomers in good to excellent yield (i.e., 70-90%) by simply allowing a hydrocarbon-MTBE solution of the iodide to stand in the presence of a small quantity of PhLi at an appropriate temperature. The mechanism of the cycloisomerization was found to be substrate dependent: unsaturated aryl and primary alkyl iodides undergo isomerization via a three-step cascade (eqs 1-3) mediated by two reversible lithium-iodine exchange reactions bracketing an irreversible 5-exo cyclization of an unsaturated organolithium; unsaturated secondary and tertiary alkyl iodides apparently isomerize via a radical-mediated atom transfer process initiated by homolytic fragmentation of the ate-complex generated upon attack of PhLi on the iodine atom of the substrate.

  DOI：

  10.1021/jo981991q
• 作为产物：
  描述：

  2-碘苯胺 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 2-iodo-N,N-diallylaniline
  参考文献：
  名称：

  Reductive radical cyclizations of haloalkenes promoted by samarium diiodide. Sequential cyclization/intermolecular carbonyl addition reactions

  摘要：

  DOI：

  10.1021/jo00312a025

文献信息

• 1,2-Difunctionalization of Aryl Triflates: A Direct and Modular Access to Diversely Functionalized Anilines
  作者：Seoyoung Cho、Qiu Wang

  DOI：10.1021/acs.orglett.0c00320

  日期：2020.2.21

  ortho-Amino difunctionalization of aryl triflates has been achieved via a three-component reaction. The cascade reaction proceeds through a zincate base-mediated deprotonative formation of a reactive aryne intermediate, in situ nucleophilic addition, and coupling with electrophilic partners. This strategy leverages the advantageous reactivity of organozincate intermediates, enabling the installation

  已通过三组分反应实现了芳基三氟甲磺酸酯的邻氨基双官能化。级联反应通过锌盐介导的反应性芳烃中间体的去质子形成，原位亲核加成以及与亲电子伴侣偶联而进行。该策略利用了有机锌酸盐中间体的有利反应性，能够以模块化的方式安装各种功能，例如胺，叠氮化物，氧，硫，卤化物，炔基，芳基，乙烯基和烷基，以合成各种苯胺骨架。
• Palladium-Catalyzed Carboacylation of Alkenes by Using Acylchromates as Acyl Donors
  作者：Motoki Yamane、Yuko Kubota、Koichi Narasaka

  DOI：10.1246/bcsj.78.331

  日期：2005.2

  Palladium-catalyzed arylacylation of alkenes proceeds by employing acylchromates as acyl donors. When active alkenes such as norbornene and methoxyallene are treated with an aryl iodide, an acylchromate, and a catalytic amount of Pd(OAc)2/2P(o-Tol)3, arylacylation of these alkenes proceeds at room temperature. From aryl iodides having an intramolecular alkene moiety, cyclization–acylation products are obtained via intramolecular arylpalladation followed by acylation with acylchromates.

  钯催化的烯烃与苯甲酰基化合物的反应中，使用了苯甲酰基铬酸盐作为酰基供体。当活性烯烃如降冰片烯和甲氧基丙二烯与芳基碘、苯甲酰基铬酸盐及催化量的 Pd(OAc)2/2P(o-Tol)3 反应时，这些烯烃在室温下即可发生芳基酰化反应。对于具有分子内烯烃的芳基碘，通过分子内芳基钯化后再与苯甲酰基铬酸盐进行酰化反应，得到环化-酰化产物。
• An efficient approach to 1,2,3-trisubstituted indole via rhodium catalyzed carbene C_sp3–H bond insertion
  作者：Mei-Hua Shen、Ying-Peng Pan、Zhi-Hong Jia、Xin-Tao Ren、Ping Zhang、Hua-Dong Xu

  DOI：10.1039/c5ob00085h

  日期：——

  A method for convenient synthesis ofN-alkyl-2-aryl-indole-3-carbaldehydeviacarbene C–H bond insertion.

  一种通过卡宾C-H键插入方便地合成N-烷基-2-芳基吲哚-3-甲醛的方法。
• Pd(II)-Catalyzed Enantioselective Oxidative Tandem Cyclization Reactions. Synthesis of Indolines through C−N and C−C Bond Formation
  作者：Kai-Tai Yip、Min Yang、Ka-Lun Law、Nian-Yong Zhu、Dan Yang

  DOI：10.1021/ja060291x

  日期：2006.3.1

  efficient Pd(II)-catalyzed enantioselective oxidative tandem cyclization strategy using molecular oxygen as a green oxidant for the double 5-exo-trig cyclizations of N-(2-allylaryl) amides to afford a variety of indolines in good yields without the formation of undesired monocyclization products. By employing Pd(TFA)2/(-)-sparteine as the chiral catalyst, we obtained tandem cyclization products with high enantioselectivity

  我们开发了一种有效的 Pd(II) 催化的对映选择性氧化串联环化策略，使用分子氧作为绿色氧化剂，用于 N-(2-烯丙基芳基) 酰胺的双 5-exo-trig 环化，以良好的收率提供各种二氢吲哚不会形成不需要的单环化产物。通过使用 Pd(TFA)2/(-)-sparteine 作为手性催化剂，我们获得了具有高对映选择性（高达 91% ee）的串联环化产物。
• Metathesis of aniline and 1,2-dihydroquinoline derivatives
  作者：Paul Evans、Ronald Grigg、Michael Monteith

  DOI：10.1016/s0040-4039(99)00993-4

  日期：1999.7

  Ring closing metathesis of N,N-diallylanilines and a related 1,2-dihydroquinoline, catalysed by Grubbs' catalyst, occurs in good yield at room temperature furnishing 3-pyrrolines and 3-piperidines. DCM and EtOAc are the solvents of choice and interesting substituent effects are identified and discussed.

  N，N-二烯丙基苯胺和相关的1，2-二氢喹啉的闭环易位反应在室温下以良好的收率进行，并提供3-吡咯啉和3-哌啶，它们由格鲁布斯的催化剂催化。DCM和EtOAc是选择的溶剂，有趣的取代基作用得到鉴定和讨论。