7-norbornylidene-7-norbornane | 51689-29-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 7-norbornylidene-7-norbornane
• 英文别名: Bicyclo[2.2.1]heptane, 7-bicyclo[2.2.1]hept-7-ylidene-；7-(7-bicyclo[2.2.1]heptanylidene)bicyclo[2.2.1]heptane
• CAS: 51689-29-3
• 化学式: C₁₄H₂₀
• 分子量: 188.313
• InChiKey: AFBGSOHTRROVJY-UHFFFAOYSA-N

物化性质

• 熔点：
  140.5-141.0 °C
• 沸点：
  273.6±7.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  7-norbornylidene-7-norbornane 在 氧气 、 tetraphenylporphyrin 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以15%的产率得到bis(bicyclo<2.2.1>heptan-7-ylidene) dioxetane
  参考文献：
  名称：

  受阻烯烃形成二氧杂环丁烷的立体化学研究

  摘要：

  Etude de la photooxygenation par l'oxygene singulet, de la photooxygenation par l'anthracenedicarbonitrile-9,10 et de l'electrooxygenation de bicyclanylidenes en dioxetanes-1,2 dispiranniques

  DOI：

  10.1021/ja00338a028
• 作为产物：
  描述：

  在 三丁基膦 作用下， 生成 7-norbornylidene-7-norbornane
  参考文献：
  名称：

  Stereochemical consequences of photosensitized and electrode-catalyzed oxygenations of stereoisomeric di-tert-butylbi(bicyclo[3.3.1]non-9-ylidene)

  摘要：

  DOI：

  10.1021/ja00389a070

文献信息

• Experimental Investigation of the Primary and Secondary Deuterium Kinetic Isotope Effects for Epoxidation of Alkenes and Ethylene with <i>m</i>-Chloroperoxybenzoic Acid
  作者：Terry Koerner、H. Slebocka-Tilk、R. S. Brown

  DOI：10.1021/jo981652x

  日期：1999.1.1

  The secondary deuterium kinetic isotope effect (DKIE) for the epoxidation of ethylene and d(4)-ethylene by m-chloroperoxybenzoic acid (MCPBA) is determined to be 0.83, or 0.95/alpha-H. The second-order rate constants for MCPBA and MCPBA-O-D epoxidation of a variety of alkenes that differ in the steric access to the double bond (anti-sesquinorbornene (2), tetramethylethylene (3), adamantylideneadamantane

  乙烯和d（4）-乙烯被间氯过氧苯甲酸（MCPBA）环氧化的次级氘动力学同位素效应（DKIE）被确定为0.83或0.95 / alpha-H。各种烯烃的MCPBA和MCPBA-OD环氧化的二阶速率常数，在空间上对双键的访问方式有所不同（抗-倍半萜烯（2），四甲基乙烯（3），金刚烷-金刚烷（4），7-降冰片烯- 7'-降冰片烷（5），双（双环[3.3.1。]非-9-亚烷基）（6），双（纯金刚烷）（7），环己烯（8），1-辛烯（9），反式-5 -二癸烷（10）和2-甲基-1-戊烯（11））已在25摄氏度下使用UV动力学在二氯乙烷中测定，主要DKIE k（OH）/ k（OD）为1.05 +/-在所有情况下均为0.05。通过比较位阻烯烃的环氧化速率，这表明螺环的环氧化过渡态优于平面的。确定抗-二喹降冰片烯的环氧化产物为环氧化物和顺式-羟基酯，后者最有可能是通过原位生成的原位生成的间氯苯甲酸经酸催化的
• Synthesis and reactions of meso- and dl-D3-trishomocubylidene-D3-trishomocubane
  作者：Alan P. Marchand、G. Madhusudhan Reddy、Mahendra N. Deshpande、William H. Watson、Ante Nagl、Oh Seuk Lee、Eiji Osawa

  DOI：10.1021/ja00165a041

  日期：1990.4

  La copulation reductive de D 3 -trishomocubane, catalyse par TiCl 4 produit essentiellement les meso et dl-D 3 -trishomocubylidene D 3 -trishomocubanes. Etude par diffraction RX de leurs structures. Etude de leur reactivite chimique vis-a-vis d'electrophiles

  La copulation reductive de D 3 -trishomocubane，催化par TiCl 4 produit essentiellement les meso et dl-D 3 -trishomocubylidene D 3 -trishomocubanes。练习曲 par 衍射 RX de leurs 结构。Etude de leur reactive chimique vis-a-vis d'electrophiles
• Synthesis and decomposition of two cyclic (four-ring) azo compounds (.DELTA.1-1,2-diazetines)
  作者：Derk J. Hogenkamp、Frederick D. Greene

  DOI：10.1021/jo00072a021

  日期：1993.9

  The DELTA1-1,2-diazetines 1 and 2 have been synthesized in three steps from N-methyltriazolinedione (MeTAD) and the olefins (adamantylideneadamantane, Ad=Ad, for 1; 7-norbornylidene-7-norbornane for 2). Diazetidine 3 (from Ad=Ad + MeTAD) undergoes ring expansion to a pyrazolidine derivative, 5 (subsequently converted to a novel pyrazoline, cyclic (five-ring) azo compound 6). The structurally-related N-methylaminocarbonyl diazetidine 4 undergoes acid-catalyzed ring contraction to N-aminoaziridine derivative 7a. Compound 7a and the corresponding N-aminoaziridine derivative 7b undergo oxidative ring expansion to afford diazetine 1, accompanied by olefin (Ad=Ad). Efforts to extend this novel synthesis of diazetines to other N-aminoaziridines (8,9a, 9b, 10) were unsuccessful, affording only the deazetation product, olefin. Thermal decomposition of diazetine 1 at 137-degrees-C in dodecane (tl/2 = 1.5 h) proceeds by two paths: ring-opening to adamantanone azine and deazetation to the olefin Ad=Ad; azine/olefin = 1.9/1. For diazetine 2, k(overall) is 60-fold slower than for 1 and azine/olefin = 1/14. Diazetine 1 is rapidly converted to olefin (Ad=Ad) at 25-degrees-C by 10 mol% of Ar3N.+ [(p-BrC6H4)3N.+ SbF6-], thought to occur by an electron transfer chain process; diazetine 2 is inert to these conditions. Relative rates of nitrogen loss for 1, 2, and tetramethyldiazetine (15c) at 137-degrees-C are 1:0.05:3. Some aspects of mechanism of thermal and catalyzed decomposition of diazetines are discussed.
• Electrophilic Bromination of 7-Norbornylidene-7'-Norbornane. The Observation of an Unusually Large Inverse Deuterium Kinetic Isotope Effect
  作者：H. Slebocka-Tilk、S. Motallebi、R. W. Nagorski、P. Turner、R. S. Brown、R. McDonald

  DOI：10.1021/ja00139a009

  日期：1995.8

  The bromination of 7-norbornylidene-7'-norbornane (1) and its perdeuterated analogue (2) was studied in HOAc and MeOH by investigating the reaction kinetics and product distributions as a function of added [Br-]. In all cases there is a significant inverse deuterium kinetic isotope effect on the bromination rate constant (k(g)) which, in HOAc, is k(g)(2/1) 1.56 and 1.83 at [Br-] = 0 and 0.04 M, respectively. Added Br- causes a significant rate retardation which indicates the intervention of a reversibly formed bromonium ion intermediate. Product studies indicate the formation of four products, a normal dibromide and beta-bromo solvate and two that arise from capture of an alpha-bromo cation formed from a Wagner-Meerwein rearrangement of the first-formed bromonium ion. In HOAc, added [Br-] leads to an increase in the amount of the normal dibromide at the expense of the solvent-incorporated and rearranged products. In MeOH, dibromide is never an important product at any [Br-] investigated, the two major isolated products being the normal methoxy bromide and rearranged ketone. Quantitative analyses of the products formed from bromination of 1 and 2 in HOAc as a function of [Br-] indicate little difference in the product partitioning that is attributable to the presence of H or D. A unified mechanism that accommodates all the data is presented.
• Nagorski; Ślebocka-Tilk; Brown, Journal of the American Chemical Society, 1994, vol. 116, # 1, p. 419 - 420
  作者：Nagorski、Ślebocka-Tilk、Brown

  DOI：——

  日期：——

表征谱图