11,12-bis(hydroxymethyl)-9,10-etheno-9,10-dihydroanthracene | 131760-69-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 11,12-bis(hydroxymethyl)-9,10-etheno-9,10-dihydroanthracene
• 英文别名: 11,12-bis(hydroxymethyl)dibenzobarrelene；11,12-di(hydroxymethyl)-9,10-dihydro-9,10-ethenoanthracene；[16-(Hydroxymethyl)-15-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13,15-heptaenyl]methanol
• CAS: 131760-69-5
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: RHFRIGGFUVDEFI-UHFFFAOYSA-N

物化性质

• 熔点：
  193-194 °C(Solvent: Chloroform)
• 沸点：
  469.504±40.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.265±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11,12-bis(hydroxymethyl)-9,10-etheno-9,10-dihydroanthracene 在 2,4,6-三甲基吡啶 、 三溴化磷 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以63%的产率得到11,12-bis(bromomethyl)-9,10-dihydro-9,10-ethenoanthracene
  参考文献：
  名称：

  Reduction of DMAD-anthracene adducts. Synthesis and conformations of substituted cyclodecadienes

  摘要：

  A general method for reducing DMAD-anthracene adducts to the corresponding enediols is described. Thus, the ester groups of 1 were reduced without C = C reduction using the DIBAH-nBuLi ''ate'' complex to give previously unknown 2 in high yield. Analogous enediols 5-7 were similarly prepared. Base treatment of dibromide 3 and dithiol 9, both prepared from 2 by standard methods, gave conformationally rigid dithiacyclodecadiene 10. With o-, m-, and p-xylylenedithiols, dibromide 3 gave respectively the conformationally labile cyclophanes 12 and 13 and the rigid cyclophane 14. Tetrabromide 16 and dithiol 9 gave cuppedophane 17, but tetrabromide 18 and 9 formed bis-m-cyclophane 19 instead.

  DOI：

  10.1021/jo00003a019
• 作为产物：
  描述：

  dimethyl 9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboxylate 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以90%的产率得到11,12-bis(hydroxymethyl)-9,10-etheno-9,10-dihydroanthracene
  参考文献：
  名称：

  Reduction of DMAD-anthracene adducts. Synthesis and conformations of substituted cyclodecadienes

  摘要：

  A general method for reducing DMAD-anthracene adducts to the corresponding enediols is described. Thus, the ester groups of 1 were reduced without C = C reduction using the DIBAH-nBuLi ''ate'' complex to give previously unknown 2 in high yield. Analogous enediols 5-7 were similarly prepared. Base treatment of dibromide 3 and dithiol 9, both prepared from 2 by standard methods, gave conformationally rigid dithiacyclodecadiene 10. With o-, m-, and p-xylylenedithiols, dibromide 3 gave respectively the conformationally labile cyclophanes 12 and 13 and the rigid cyclophane 14. Tetrabromide 16 and dithiol 9 gave cuppedophane 17, but tetrabromide 18 and 9 formed bis-m-cyclophane 19 instead.

  DOI：

  10.1021/jo00003a019

文献信息

• Design of a Chiral Mesoporous Silica and Its Application as a Host for Stereoselective Di-π-methane Rearrangements
  作者：Miriam Benitez、Gerhard Bringmann、Michael Dreyer、Hermenegildo Garcia、Heiko Ihmels、Michael Waidelich、Kathrin Wissel

  DOI：10.1021/jo047878j

  日期：2005.3.1

  A chiral periodic mesoporous organosilica (ChiMO) was prepared, in which a 1,2-bis-(ureido)cyclohexyl linker (38 wt %) is introduced into the walls of the hybrid organic−inorganic material. This silica was used as a host for 11-formyl-12-methyldibenzobarrelene (2), and the stereoselectivity of the di-π-methane rearrangement of 2 within this host−guest complex was studied. At low conversions, the only

  制备了手性周期性介孔有机硅（ChiMO），其中将1,2-双-（脲基）环己基连接基（38 wt％）引入到杂化有机-无机材料的壁中。该二氧化硅用作11-甲酰基-12-甲基二苯并戊烯（2）的主体，并研究了该主体-客体复合物中2的二-π-甲烷重排的立体选择性。在低转化率下，唯一的产物是相应的二苯并半bullvalvalene。使用ChiMO作为宿主，在11％的转化率下对映体过量为24％。这些值与使用基于常规八面沸石（LiY和NaY）的系统作为手性助剂的宿主所获得的值相当。我们测试了S-苯甘氨酸，S-脯氨酸，S-樟脑酸和S-扁桃酸作为手性助剂。与ChiMO材料的行为相反，在含有麻黄碱的纯硅质介孔MCM-41二氧化硅（孔径为3.2 nm）中，二苯并戊烯烯的吸附失败，这可以解释为是由于内部硅烷醇含量高和亲水性高而引起的。硅质MCM-41样品。
• Medium-Dependent Type Selectivity in Photoreactions of a Crown Ether-Annelated Dibenzobarrelene Derivative
  作者：Heiko Ihmels、Michael Schneider、Michael Waidelich

  DOI：10.1021/ol026482w

  日期：2002.9.1

  [reaction: see text] A concept for modifying the photochemical properties of a dibenzobarrelene derivative by the combination of supramolecular assembly and solid-state photochemistry is presented. The irradiation of dibenzobarrelene 1b and alkali metal complexes thereof (1:1) in acetonitrile or benzene solution leads preferentially to the dibenzocyclooctatetraene 4b as the photoproduct. In contrast

  [反应：见正文]提出了一种通过超分子组装和固态光化学的结合来改变二苯并桶烯衍生物的光化学性质的概念。在苯腈或苯溶液中辐照二苯并戊烯1b及其碱金属配合物（1：1）优先产生作为光产物的二苯并环辛酸酯四烯4b。相反，由于强的阳离子作用，二苯并半bullvalene 5b形成为固态的主要光产物。
• ANANTANARAYAN, ASHOK;HART, HAROLD, J. ORG. CHEM., 56,(1991) N, C. 991-996
  作者：ANANTANARAYAN, ASHOK、HART, HAROLD

  DOI：——

  日期：——
• Reduction of DMAD-anthracene adducts. Synthesis and conformations of substituted cyclodecadienes
  作者：Ashok Anantanarayan、Harold Hart

  DOI：10.1021/jo00003a019

  日期：1991.2

  A general method for reducing DMAD-anthracene adducts to the corresponding enediols is described. Thus, the ester groups of 1 were reduced without C = C reduction using the DIBAH-nBuLi ''ate'' complex to give previously unknown 2 in high yield. Analogous enediols 5-7 were similarly prepared. Base treatment of dibromide 3 and dithiol 9, both prepared from 2 by standard methods, gave conformationally rigid dithiacyclodecadiene 10. With o-, m-, and p-xylylenedithiols, dibromide 3 gave respectively the conformationally labile cyclophanes 12 and 13 and the rigid cyclophane 14. Tetrabromide 16 and dithiol 9 gave cuppedophane 17, but tetrabromide 18 and 9 formed bis-m-cyclophane 19 instead.