2-bromocyclohexa-1,3-diene | 3727-48-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2-bromocyclohexa-1,3-diene
• 英文别名: 1,3-Cyclohexadiene, 2-bromo
• CAS: 3727-48-8
• 化学式: C₆H₇Br
• 分子量: 159.026
• InChiKey: IYBFVRUXEKUNNQ-UHFFFAOYSA-N

物化性质

• 保留指数：
  980

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-bromocyclohexa-1,3-diene 在 platinum(IV) oxide 四(三苯基膦)钯 、 草酰氯 、 四溴化碳 、 lithium amidotrihydroborate 、 molybdenum hexacarbonyl 、 氢气 、 sodium carbonate 、 magnesium 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 氯仿 、 水 、 乙腈 为溶剂， -78.0~70.0 ℃ 、101.33 kPa 条件下， 反应 112.75h， 生成 (±)-三色素蛙素
  参考文献：
  名称：

  Total Synthesis of (−)-Epibatidine Using an Asymmetric Diels−Alder Reaction with a Chiral N-Acylnitroso Dienophile

  摘要：

  An asymmetric total synthesis of(-)-epibatidine (1), isolated from the skin of the Ecuadorian poison frog, Epipedobates tricolor, of the family Dendrobatidae, has been achieved by virtue of the development of asymmetric hetero Diels-Alder (D-A) cycloaddition with an N-acylnitroso dienophile bearing the optically active 8-arylmenthol as a chiral source. Thus, in situ oxidation of the hydroxamic acid ent-laf incorporating the (1S,2R,5S)-8-(2-naphthyl)menthyl auxiliary was performed using the Swern conditions to produce the acylnitroso dienophile, which reacted at once with 2-chloro-5-(1,5-cyclohexadienyl)pyridine (7) to provide the (1S,4R)-meta-aza cycloadduct 24 as a major diastereoisomer. The observed facial diastereoselectivity is consistent with a transition-state model with the naphthyl group in "stacked" position and with the acylnitroso group in the s-cis conformation, wherein pi attractive interaction between the naphthyl and nitrosocarbonyl groups may contribute to facial control. Compound 24 underwent hydrogenation followed by removal of the chiral auxiliary with LiH2NBH3 and reductive cleavage of the N-O bond with Mo(CO)(6) to give the amino alcohol derivative 29, which was converted to (-)-epibatidine via bromination followed by cyclization.

  DOI：

  10.1021/jo9813078
• 作为产物：
  描述：

  2-bromocyclohex-2-en-1-ol 在 四(三苯基膦)钯 1-甲基吡咯烷 、 吡啶 作用下， 以 乙醚 为溶剂， 反应 21.0h， 生成 2-bromocyclohexa-1,3-diene
  参考文献：
  名称：

  Chemoselectivity in palladium-catalyzed reactions of 2-bromoallyl esters

  摘要：

  DOI：

  10.1021/jo00220a043

文献信息

• Simple and efficient synthesis of bromine-substituted 1,3-dienes and 1,3,5-cycloheptatriene by vacuum pyrolysis of gem-dibromocyclopropanes
  作者：Nick H Werstiuk、Chandra D Roy

  DOI：10.1016/s0040-4039(01)00460-9

  日期：2001.5

  6-dibromobicyclo[3.1.0]hexane (5) and 7,7-dibromobicyclo[4.1.0]heptane (6). Except 7,7-dibromobicyclo[4.1.0]heptane, that gave 1,3,5-cycloheptatriene in 72% yield at 525°C, 1, 2, 3, 4 and 5 readily lose HBr at 400–560°C in the gas phase to produce β-bromo-1,3-dienes in high chemical yields and purity. The dienes are potentially useful starting substrates for the Diels–Alder reactions.

  为了确定是否可以通过改进的方法在制备规模上获得使用高功率CW CO 2激光作为定向热源通过HeI光电子能谱通过HeI光电子光谱对6,6-二卤代双环[3.1.0]己烷进行气相热解而获得的结果装置中，我们进行了几种代表性的宝石-二溴环丙烷的气相热解，例如1,1-二溴-2,2,3,3-四甲基环丙烷（1），1,1-二溴-2,2-二甲基环丙烷（2），1，1-二溴-顺式-2,3-二甲基环丙烷（3），1,1-二溴-反式-2,3-二甲基环丙烷（4），6,6-二溴双环[3.1.0]己烷（5）和7,7-二溴双环[4.1.0]庚烷（6）。除了7,7- dibromobicyclo [4.1.0]庚烷，这给了1,3,5-环庚三烯在72％的产率在525℃下，1，2，3，4和5中容易失去的HBr在400-560℃下在气相中以高化学产率和纯度生产β-溴-1,3-二烯。二烯是Diels–Alder反应的潜在有用起始底物。
• ANTHRACENE COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME
  申请人：Yen Feng-Wen

  公开号：US20080299294A1

  公开（公告）日：2008-12-04

  The present invention discloses an anthracene compound which can be used as emitting material in organic electroluminescence devices is disclosed. The mentioned anthracene compound is represented by the following formula [I] Wherein Ar 1 and Ar 2 are the same or different and each is selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted anthryl group.

  本发明公开了一种蒽化合物，可用作有机电致发光器件中的发光材料。所述的蒽化合物由以下式[I]表示其中Ar1和Ar2相同或不同，并且每个都选自取代或未取代的苯基，取代或未取代的萘基，取代或未取代的联苯基，取代或未取代的芴基，取代或未取代的蒽基。
• A Synthesis of the Carbocyclic Core of Maoecrystal V
  作者：Kiel E. Lazarski、Dennis X. Hu、Charlotte L. Stern、Regan J. Thomson

  DOI：10.1021/ol101025r

  日期：2010.7.2

  An approach toward the synthesis of the complex polycyclic diterpene maoecrystal V (1) is described. Construction of the advanced tetracyclic core structure (i.e., 19) was achieved in 13 steps from 3,3-dimethylcyclohexanone (6) by employing a stereoselective Nazarov cyclization followed by a Diels−Alder reaction to forge the two contiguous quaternary stereocenters.

  描述了一种合成复杂的多环二萜微晶 V ( 1 ) 的方法。高级四环核心结构（即19）的构建是从 3,3-二甲基环己酮（6）通过立体选择性 Nazarov 环化和 Diels-Alder 反应以形成两个连续的四元立体中心的13 个步骤实现的。
• Mesomeric Vinyl Cations. Part III. Stereochemistry of cations derived from 2-bromo-1, 3-dienes
  作者：C. A. Grob、H. R. Pfaendler

  DOI：10.1002/hlca.19700530825

  日期：——

  In contrast to their acyclic analogues, 2-bromocyclohexa-1, 3-diene (11a) and 3-bromo-1, 5-dimethyl-cyclohexa-1, 3-diene (11b) do not react with silver ion, nor do they undergo solvolysis in 80% ethanol at temperatures up to 180°. The inertness to ionization of these cyclic bromodienes is attributed to steric inhibition of mesomerism involving the π electrons of the second double bond in the planar

  与它们的无环类似物相反，2-溴环己-1，3-二烯（11a）和3-溴-1，5-二甲基-环己-1，3-二烯（11b）不会与银离子反应，它们也不会在温度高达180°的80％乙醇中进行溶剂分解。这些环状溴代二茂铁化合物电离的惰性归因于在平面乙烯基阳离子12中涉及第二双键的π电子的介旋异构的空间抑制以及该假设中间体的弯曲结构。
• [EN] NOVEL COMPOUNDS HAVING INHIBITORY ACTIVITY AGAINST SODIUM-DEPENDANT TRANSPORTER<br/>[FR] NOUVEAUX COMPOSES POSSEDANT UNE ACTIVITE INHIBITRICE DIRIGEE CONTRE LE TRANSPORTEUR DEPENDANT DU SODIUM
  申请人：TANABE SEIYAKU CO

  公开号：WO2005012326A1

  公开（公告）日：2005-02-10

  A compound of the formula (I) wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is -(CH2)n- (n is 1 or 2); a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  化合物的式子（I）其中环A和环B为：（1）环A是可选取代的不饱和单环杂环，环B是可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环，（2）环A是可选取代的苯环，环B是可选取代的不饱和单环杂环或可选取代的不饱和融合杂双环，或（3）环A是可选取代的不饱和融合杂双环，环B独立地是可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；X是碳原子或氮原子；Y是-(CH2)n-（n为1或2）；其药物可接受的盐或前药。