1,4-二溴-1,2,3,4-四氢萘 | 6606-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 1,4-二溴-1,2,3,4-四氢萘
• 英文名称: 1,4-dibromo-1,2,3,4-tetrahydronaphthalene
• 英文别名: 1,4-dibromo-1,2,3,4-tetrahydro-naphthalene；1,4-Dibrom-1,2,3,4-tetrahydro-naphthalin；1,4-Dibromo-1,2,3,4,tetrahydronaphthalen；1,4-Dibrom-tetralin；trans-1,4-Dibromo-1,2,3,4-tetrahydronaphthalene
• CAS: 6606-70-8
• 化学式: C₁₀H₁₀Br₂
• 分子量: 289.997
• InChiKey: ALQRYBAMWLAYNB-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C
• 沸点：
  308.8±37.0 °C(Predicted)
• 密度：
  1.757±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• 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：

  1,4-二溴-1,2,3,4-四氢萘 在 sodium hydroxide 、 四乙基溴化铵 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,4-二氢-1,4-乙基桥萘
  参考文献：
  名称：

  The anodic oxidation of cis-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylic acid and its derivatives: competition between oxidative bisdecarboxylation and dilactone formation

  摘要：

  DOI：

  10.1021/jo00065a023
• 作为产物：
  描述：

  1,2,3,4-四氢萘 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 0.33h， 生成 1,4-二溴-1,2,3,4-四氢萘
  参考文献：
  名称：

  Asymmetric Acylation of sec-Alcohols with Twisted Amides Possessing Axial Chirality Induced by the Adjacent Asymmetric Center

  摘要：

  This paper reports that axially chiral twisted amides serve as asymmetric acylating agents for sec-alcohols under neutral conditions. Kinetic resolution of various racemic sec-alcohols and desymmetrization of 1,2-, 1,3-, and 1,4-meso-diols were performed by using the twisted amides. The utility of this desymmetrization method was shown by the preparation of the synthetic intermediate 28 for macrolide antibiotic nodusmicin and 18-deoxynargenicin. The stereoselectivity of the acylation reactions is significantly dependent on the bulkiness of both the acyl group and the C-4 substituent of the chiral auxiliary. When an amide possessing an imidazolyl group at C-4 was employed, the stereoselectivity was reversed to give R esters. A possible working model of the acylation reaction is also described on the basis of the structural studies of the twisted amides by IR and H-1 and C-13 NMR spectroscopies and AM1 calculations. These studies suggested that rotamer II is thermodynamically more stable than the others. The rotamer II has an axial chirality about its C(O)-N linkage that is induced by the adjacent chiral center. This would enable discrimination of the two enantiomeric hydroxy groups of the racemic alcohols or meso-diols.

  DOI：

  10.1021/jo990892p

文献信息

• Synthesis of New Diphosphine Ligands and their Application in Pd-Catalyzed Alkoxycarbonylation Reactions
  作者：Anahit Pews-Davtyan、Xianjie Fang、Ralf Jackstell、Anke Spannenberg、Wolfgang Baumann、Robert Franke、Matthias Beller

  DOI：10.1002/asia.201301636

  日期：2014.4

  Carbocyclic and N‐heterocyclic analogues of the industrially applied ligand bis(di‐tert‐butylphosphinomethyl)benzene (1) have been synthesized in moderate to very good yields. The new ligands are based on benzene, tetralin, lutidine, pyrazine, quinoxaline, and maleimide backbones. Electronic and steric variations of the phosphorous donor sites were performed. As a benchmark reaction, the palladium‐catalyzed

  工业应用的配体双（二叔丁基膦基甲基）苯（1）的碳环和N杂环类似物的合成产率中等至非常高。新的配体基于苯，四氢萘，二甲基吡啶，吡嗪，喹喔啉和马来酰亚胺骨架。进行了磷供体位点的电子和空间变化。作为基准反应，已经测试了钯催化的1-辛烯的甲氧基羰基化。酯产率高达64％，线性选择性高达92％。
• Investigations in the cyclobutane series—X
  作者：Margaret Avram、I.G. Dinulescu、Doina Dinu、G. Mateescu、C.D. Nenitzescu

  DOI：10.1016/s0040-4020(01)98532-1

  日期：1963.1

  Dibenzotricycloöctadiene (I) yields on heating with dienophiles, Diels-Alder adducts (IV and V) and forms with oxygen a peroxide (VI). These reactions are explained by formation of an intermediate with an ortho-quinonoid structure (II). Polycyclic Diels-Alder adducts were obtained in good yields from a solution of benzocyclobutadiene and unstable hydrocarbons such as ortho-quinodimethane or 2,3-dihydronaphthalene

  二苯并三环十八碳二烯（I）与亲二烯体，狄尔斯-阿尔德加合物（IV和V）加热生成，并与氧形成过氧化物（VI）。这些反应通过形成具有邻-醌型结构（II）的中间体来解释。从苯并环丁二烯和不稳定的烃类如邻-喹二甲烷或2,3-二氢萘的溶液以良好的产率获得多环Diels-Alder加合物。对于先前获得的几种化合物，提出了修订的结构。1个
• [EN] LEAVING SUBSTITUENT-CONTAINING COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL, ORGANIC SEMICONDUCTOR FILM CONTAINING THE MATERIAL, ORGANIC ELECTRONIC DEVICE CONTAINING THE FILM, METHOD FOR PRODUCING FILM-LIKE PRODUCT, PI-ELECTRON CONJUGATED COMPOUND AND ME<br/>[FR] COMPOSITION CONTENANT UN SUBSTITUANT PARTANT, MATÉRIAU SEMI-CONDUCTEUR ORGANIQUE, FILM SEMI-CONDUCTEUR ORGANIQUE CONTENANT CE MATÉRIAU, DISPOSITIF ÉLECTRONIQUE ORGANIQUE CONTENANT CE FILM, PROCÉDÉ DE PRODUCTION DE PRODUIT EN FORME DE FILM, COMPOSÉ À
  申请人：RICOH CO LTD

  公开号：WO2011030918A1

  公开（公告）日：2011-03-17

  A leaving substituent-containing compound including a partial structure represented by the following General Formula (I): where a pair of X1 and X2 or a pair of Y1 and Y2 each represent a hydrogen atom; the other pair each represent a group selected from the group consisting of a halogen atom and a substituted or unsubstituted acyloxy group having one or more carbon atoms; a pair of the acyloxy groups represented by the pair of X1 and X2 or the pair of Y1 and Y2 may be identical or different, or may be bonded together to form a ring; R1 to R4 each represent a hydrogen atom or a substituent; and Q1 and Q2 each represent a hydrogen atom, a halogen atom or a monovalent organic group, and may be bonded together to form a ring.

  一种含有离去基团的化合物，包括由以下通用式（I）表示的部分结构：其中一对X1和X2或一对Y1和Y2分别代表氢原子；另一对分别代表从卤素原子和具有一个或多个碳原子的取代或未取代的酰氧基团组成的群中选择的基团；由X1和X2或Y1和Y2组成的酰氧基团对可以相同或不同，或者可以结合在一起形成环；R1至R4分别代表氢原子或取代基；Q1和Q2分别代表氢原子、卤素原子或一价有机基团，并且可以结合在一起形成环。
• Bromination of Tetralin. Short and Efficient Synthesis of 1,4-Dibromonaphthalene
  作者：Osman Çakmak、Ismail Kahveci、Íbrahim Demirtaş、Tuncer Hökelek、Keith Smith

  DOI：10.1135/cccc20001791

  日期：——

  High-temperature bromination of tetralin (1,2,3,4-tetrahydronaphthalene) with bromine resulted in benzylic bromination to give 1,4-dibromo-1,2,3,4-tetrahydronaphthalene (4) as a major product and several secondary products. Photolytic bromination of tetralin and subsequent double dehydrobromination of 1,1,4,4-tetrabromo-1,2,3,4-tetrahydronaphthalene (10) gave 1,4-dibromonaphthalene (11) as the sole product in a high yield. 1,4-Dibromonaphthalene is efficiently converted to the corresponding methoxy (12 and 13) and cyano (14 and 15) derivatives of naphthalene.

  高温溴化四氢萘（1,2,3,4-四氢萘）与溴反应，产生苄溴化反应，生成1,4-二溴-1,2,3,4-四氢萘（4）作为主要产物，以及几种次生产物。四氢萘的光解溴化反应和随后的1,1,4,4-四溴-1,2,3,4-四氢萘（10）的双去溴反应，高产率地生成1,4-二溴萘（11）作为唯一产物。1,4-二溴萘有效地转化为相应的甲氧基（12和13）和氰基（14和15）萘衍生物。
• ACID-LABILE POLYMERS AND MONOMERS FOR THEIR CONSTRUCTION
  申请人：Brainard Robert L.

  公开号：US20110152496A1

  公开（公告）日：2011-06-23

  Polymers for photoresists and monomers for incorporation into those polymers are disclosed. The polymers comprise at least two components: an acid labile component and a photolytically stable and acid-stable component. The polymers may also contain a third, photoacid generator (PAG) component.

  本发明披露了用于光刻胶的聚合物和用于纳入这些聚合物的单体。聚合物至少包含两个组分：一个酸敏感组分和一个光解稳定和酸稳定组分。聚合物还可以包含第三个光酸发生剂（PAG）组分。