1,2,3,9-tetramethoxy-5H-dibenzocycloheptene | 127825-88-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2,3,9-tetramethoxy-5H-dibenzocycloheptene
• 英文别名: 1,2,3,9-tetramethoxy-5H-dibenzo[a,c]cycloheptene；1,2,3,9-Tetramethoxy-5H-dibenzo[a,c]cyclohepten；5,13,14,15-tetramethoxytricyclo[9.4.0.02,7]pentadeca-1(15),2(7),3,5,8,11,13-heptaene
• CAS: 127825-88-1
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: BCWFDUAJFIKIAR-UHFFFAOYSA-N

物化性质

• 熔点：
  102-103 °C(Solv: methanol (67-56-1))
• 沸点：
  478.0±45.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3,9-tetramethoxy-5H-dibenzocycloheptene 在 锂硼氢 、 硼烷四氢呋喃络合物 、 草酰氯 、 Zn(N3)2-2 pyr 、 偶氮二甲酸二异丙酯 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 三苯基膦 、 3-硝基苯硼酸L-酒石酸酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 47.08h， 生成 N-乙酰基秋水仙醇甲基醚
  参考文献：
  名称：

  二苯并环庚烷合成中的分子内尼古拉斯反应。NSC 51046及其同系物的合成及（-）-Alocolchicine的形式合成

  摘要：

  描述了通过联芳基-2-炔丙醇-Co 2（CO）6衍生物的分子内尼古拉斯反应制备二苯并环庚炔-Co 2（CO）6配合物。对二苯并环庚炔-Co 2（CO）6配合物进行还原性分解，得到相应的对二苯并环庚烯，其中的单个成员已用于（-）-金属酚chicine的正式全合成中，制备6,7-dihydro-3,4， 9,10,11-五甲氧基-5 H-二苯并[ a，c ]环庚烯-5-酮和NSC 51046及其3,8,9,10-四甲氧基区域异构体的对映选择性合成。

  DOI：

  10.1021/jo101953n
• 作为产物：
  描述：

  colchinolmethyl ether 生成 1,2,3,9-tetramethoxy-5H-dibenzocycloheptene
  参考文献：
  名称：

  Oxidation of Gas Mixtures Containing Dimethyl Sulfide, Hydrogen Sulfide, and Methanethiol Using a Two-Stage Biotrickling Filter

  摘要：

  A biofiltration technique was developed for removing a mixture of hydrogen sulfide (H2S), methanethiol (MeSH), and dimethyl sulfide (Me2S) from waste gases. Since H2S, especially at high concentrations, disturbs the removal of Me2S, two biotrickling filters with different microbes and operating pH levels were connected in series to create a two-stage system. Different loads of these gases were studied in order to determine their impact on the removal capacity of the system. The microbial consortia for these filters were enriched from the sludge of a Finnish refinery with bubbling H2S or Me2S. Acclimation for Me2S took 2 weeks, though no acclimation time was needed for the other gases. The first filter, at a pH of 2, removed most of the H2S and some of the MeSH and Me2S. The second filter, at a pH of similar to6.5, removed the rest of the MeSH and most of the Me2S. The total maximum loads of the whole two-stage biotrickling filter were 1150 g/m(3)/day for H2S-S (suffix S indicates the results are counted as sulfur amounts), 879 g/m(3)/day for Me2S-S, and 66 g/m(3)/day for MeSH-S treated in a gas mixture. The average removal efficiencies for all gases tested were 99% or higher.

  DOI：

  10.1080/10473289.2001.10464260

文献信息

• Deaminocolchinyl Methyl Ether: Synthesis from 2,3,4,4′-Tetramethoxybiphenyl-2-carbaldehyde. Comparison of antitubulin effects of deaminocolchinyl methyl ether and dehydro analogs
  作者：Olivier Boyé、Yoshikuni Itoh、Arnold Brossi

  DOI：10.1002/hlca.19890720805

  日期：1989.12.13

  Synthesis of deaminocolchinyl methyl ether 9 was achieved from tetramethoxy-substituted biphenyl-2-carb-aldehyde 12via tricyclic ketone 20 and 5,6-didehydro congener 11. Compound 9 was identical in every respect with material prepared from colchicine via 6,7-didehydro congener 10. Measuring inhibition of tubulin polymerization in vitro showed compounds 4, 5, and 9–11 of the alloseries of colchicinoids

  由四甲氧基取代的联苯-2-碳-醛12经由三环酮20和5，6-二氢同系物11合成了脱氨基联苯甲酰基甲基醚9。化合物9在各个方面与经由秋水仙碱经6,7-二氢同系物10制备的材料相同。测量微管蛋白聚合的抑制在体外表现出的化合物4，5，和9 - 11秋水仙碱的alloseries的是特别有效的抑制剂。
• Cook et al., Journal of the Chemical Society, 1944, p. 322,324
  作者：Cook et al.

  DOI：——

  日期：——
• Cook et al., Journal of the Chemical Society, 1952, p. 607,610
  作者：Cook et al.

  DOI：——

  日期：——
• Allocolchicines via Intramolecular Nicholas Reactions:  The Synthesis of NSC 51046
  作者：Sinisa Djurdjevic、James R. Green

  DOI：10.1021/ol7024422

  日期：2007.12.1

  Biaryl propargyl acetate hexacarbonyldicobalt complexes (4) undergo Lewis acid mediated Nicholas reactions with a remote arene function to afford dibenzocycloheptyne complexes (9). Reductive decomplexation based on a hydrosilylation-protodesilylation protocol is facile, and the 1,2,3,9-tetramethoxy case can be converted to NSC 51046 ((S)-N-acetylcolchicinol methyl ether, 3).
• Antitumor agents. Part 215:
  作者：Shiqing Han、Ernest Hamel、Kenneth F Bastow、Andrew T McPhail、Arnold Brossi、Kuo-Hsiung Lee

  DOI：10.1016/s0960-894x(02)00635-2

  日期：2002.10

  N-Acetylcolchinol methyl ether 1 served as the starting material to prepare the chloroacetamide (3) and epoxide (5) analogues. Both 3 and 5 were potent inhibitors of tubulin polymerization in vitro. Compound 3 was also 4-fold more cytotoxic than colchicine against the 1A9 tumor cell line and showed a unique cross-resistance profile. (C) 2002 Elsevier Science Ltd. All rights reserved.