11,12-Bis-hydroxymethyl-9,10-dihydro-9,10-ethano-anthracen | 26495-88-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: 11,12-Bis-hydroxymethyl-9,10-dihydro-9,10-ethano-anthracen
• 英文别名: [16-(hydroxymethyl)-15-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl]methanol
• CAS: 26495-88-5；33216-02-3
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: JRUAWKGGVJZZQC-UHFFFAOYSA-N

物化性质

• 熔点：
  226-227 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  453.9±25.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 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-dihydro-9,10-ethano-anthracen 在 吡啶 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 9,10-dihydro-11,12-dimethylene-9,10-ethanoanthracene
  参考文献：
  名称：

  内部自由体积的纳入：茂茂茂茂的聚丁二烯的合成与表征

  摘要：

  DOI：

  10.1021/ma0354694
• 作为产物：
  描述：

  dibenzobarallene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到11,12-Bis-hydroxymethyl-9,10-dihydro-9,10-ethano-anthracen
  参考文献：
  名称：

  内部自由体积的纳入：茂茂茂茂的聚丁二烯的合成与表征

  摘要：

  DOI：

  10.1021/ma0354694
• 作为试剂：
  描述：

  丙醇 、 N-(2,6-difluorophenyl)-1-[(2-hydroxyphenyl)methyl]-1H-pyrazole-3-carboxamide 在 copper(l) iodide 、 11,12-Bis-hydroxymethyl-9,10-dihydro-9,10-ethano-anthracen 、 caesium carbonate 作用下， 反应 0.42h， 生成 N-(2,6-difluorophenyl)-1-{[2-({[3-(propyloxy)phenyl]methyl}oxy)phenyl]methyl}-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  [EN] PYRAZOLE AND TRIAZOLE CARBOXAMIDES AS CRAC CHANNEL INHIBITORS
  [FR] PYRAZOLE ET TRIAZOLE CARBOXAMIDES EN TANT QU'INHIBITEURS DU CANAL CRAC

  摘要：

  本发明涉及式(I)的酰胺化合物，其制备方法，可用于这些方法的中间体，含有这些化合物的药物组合物以及它们在治疗中的应用。

  公开号：

  WO2010122088A1

文献信息

• Towards enantiopure macrocyclic trans-dinucleating hemilabile P-Alkene ligands: Syntheses, structures, and Chiral Pd-Complexes
  作者：Sibylle Frieß、Alberto Herrera、Anthony Linden、Frank W. Heinemann、Romano Dorta

  DOI：10.1016/j.jorganchem.2019.120876

  日期：2019.10

  phosphoramidite P-alkene hybrid ligands. Complexation experiments with PdCl2 reveal highly selective formation of the trans-dinuclear complex (all-R)-11. The corresponding bulkier and rigidly trans-eclipsed 1,4-diol (S,S)-bis-hydroximethyl-9,10-dihydro-9,10-ethaneanthracene (4) does not favor macrocycle formation and exclusively leads to the new dibenzazepinyl phsophormaidite P-alkene ligand 7, which in Pd-catalyzed

  Dibenzazepinyl二氯膦2下进行反应与（R，R）-2,3- Ô异亚丙基苏糖醇（3在Et）2 O解决方案，得到对映体纯的大环的亚磷酰胺（革兰氏量所有-R ）- 6，其可以被看作作为经典亚磷酰胺P-烯烃杂化配体的正式二聚体。与PdCl 2的络合实验揭示了反式-核络合物（all-R）-11的高度选择性形成。相应的笨重和刚性地反式黯然失色-1,4-二醇（小号，小号）-bis-hydroximethyl-9,10-dihydro-9,10-ethaneanthracene（4）不利于大环的形成，并仅导致形成新的二苯并ze庚基膦基镁橄榄石P-烯烃配体7，该配体在Pd催化的不对称烯丙基胺化反应中反应良好就对映体而言，已知的“特权”的由二元醇衍生的对烯烃类似物1是封闭的。
• Palladium Complexes with Bulky Diphosphine Ligands as Highly Selective Catalysts for the Synthesis of (Bio-) Adipic Acid from Pentenoic Acid Mixtures.
  作者：Choon Heng Low、James D. Nobbs、Martin van Meurs、Ludger P. Stubbs、Eite Drent、Srinivasulu Aitipamula、Michelle H. L. Pung

  DOI：10.1021/acs.organomet.5b00517

  日期：2015.9.14

  A series of sterically bulky diphosphines have been prepared, including P-2 = trans-1,2-bis[(di-tert-butylphosphino)methyllcydohexane (4), (2-methylenepropane1,3-diy1)bis(di-tert-butylphosphine) (5), bis[(di-tertbutylphosphino)methyl]dimethylsilane (6), and cis- and trans11,12-bis [ (di-tert-butylphosphino)methy1]-9,10-dihydro-9,10-ethanoanthracene (10 and 11). The corresponding palladium complexes of these ligands, P2Pd(CF3CO2)(2), have been synthesized and characterized. The solid-state structures of [Pd(4)(CF3CO2)(2)], [Pd(S)(CF3CO2)(2)], [Pd(6)(CF3CO2)(2)], and [Pd(11)(CF3CO2)(2)] were obtained by single-crystal X-ray diffraction and confirm the bidentate binding mode of the ligand and a square-planar coordination geometry with a minor distortion from the ideal. The diphosphines in combination -with Pd(OAc)(2) have been applied in the hydroxycarbonylation of a mixture of pentenoic acid isomers to produce adipic acid with high selectivity (in several cases >95%). The (regio)selectivity of the hydroxycarbonylation reaction is highly dependent on the P-2 diphosphine ligand structure, particularly the steric bulk of the substituents on the diphosphine donor and the P-Pd-P bite angle in the complexes, with respectively tertiary alkyl phosphine substituents (tert-butyl, adamantyl) and a C4 backbone P-Pd-P bite angle >100 degrees being the common features of highly adipic acid selective systems. It is suggested that the regioselectivity of hydroxycarbonylation becomes largely driven by the chelation of the carboxylic acid functionality of pentenoic acid substrates, when smaller size P substituents and/or when P-2 ligands with smaller bite angles (<100 degrees) are applied.
• SKVARCHENKO V. R.; KOSHKINA N. P., ZH. ORGAN. XIMII, 1979, 15, HO 11, 2367-2370
  作者：SKVARCHENKO V. R.、 KOSHKINA N. P.

  DOI：——

  日期：——
• BRUNNER, H.;ZETTLMEIER, W., BULL. SOC. CHIM. BELG., 100,(1991) N, C. 247-257
  作者：BRUNNER, H.、ZETTLMEIER, W.

  DOI：——

  日期：——
• BRAILLON, B.;CAIRE, J. -C.;SAQUET, M.;THUILLIER, A., J. CHEM. RES. SYNOP., 1986, N 3, 98-99
  作者：BRAILLON, B.、CAIRE, J. -C.、SAQUET, M.、THUILLIER, A.

  DOI：——

  日期：——

表征谱图