<3-(benzyloxy)-4-methoxybenzyl>phosphonium bromide | 116518-95-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: <3-(benzyloxy)-4-methoxybenzyl>phosphonium bromide
• 英文别名: <3-(benzyloxy)-4-methoxybenzyl>triphenylphosphonium bromide；(3-benzyloxy-4-methoxy-benzyl)-triphenyl-phosphonium bromide；(4-Methoxy-3-phenylmethoxyphenyl)methyl-triphenylphosphanium;bromide
• CAS: 116518-95-7
• 化学式: Br*C₃₃H₃₀O₂P
• 分子量: 569.478
• InChiKey: WGSIVJPQJTZRMD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <3-(benzyloxy)-4-methoxybenzyl>phosphonium bromide 在 palladium on activated charcoal potassium tert-butylate 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.67h， 生成 2-甲氧基-5-[2-(3,4,5-三甲氧基苯基)乙基]苯酚
  参考文献：
  名称：

  Synthesis of alkoxy-substituted diaryl compounds and correlation of ring separation with inhibition of tubulin polymerization: differential enhancement of inhibitory effects under suboptimal polymerization reaction conditions

  摘要：

  A number of cytostatic compounds (2-4, 7, and 8), which can be described as ''diaryl'', inhibit tubulin polymerization, cause cells to accumulate in mitotic arrest, and competitively inhibit the binding of colchicine to tubulin. They differ, however, in the separation of the two aryl moieties. To attempt to understand this variability we prepared a series of analogues modeled on 3 and 4 (''benzodioxole series'') and on 7 and 8 (''combretastatin series'') which differed only in the number of methylene units (ranging from none to four) separating the aryl moieties. These compounds were evaluated for their effects on tubulin polymerization, colchicine binding, and the growth of L1210 murine leukemia cells. In terms of inhibitory effects on tubulin polymerization, for the combretastatin series there was an optimal separation of the two phenyl rings by a two-carbon bridge (compound 24), with progressively decreasing inhibitory activity when the separation was by one carbon (20), three carbons (25), or four carbons (28) (the biphenyl analogue 16 was inactive). The benzodioxole series, however, did not permit us to generalize this finding, because the least active agents prepared (39 and 40) had a two-carbon bridge, while those with one- (5 and 6) and three-carbon (46 and 47) bridges were nearly equivalent in potency. Submicromolar IC50 values for inhibition of L1210 cell growth were only obtained for compounds 20 (IC50, 0.2-mu-M), 24 (0.07-mu-M), and 25 (0.4-mu-M). While evaluating the effects of these agents on tubulin polymerization, we noted with the combretastatin series and with several standard agents that apparent potency (in terms of IC50 values) was always lower if the reaction was performed at 30-degrees-C, with 0.25 mM MgCl2, than at 37-degrees-C, with 1.0 mM MgCl2. This enhancement of IC50 values in the former system as compared with the latter was particularly dramatic for the less active agents (e.g., 28) as compared with the more active (e.g. 24).

  DOI：

  10.1021/jm00084a011
• 作为产物：
  描述：

  3-羟基-4-甲氧基苯甲酸 在 三溴化磷 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 28.0h， 生成 <3-(benzyloxy)-4-methoxybenzyl>phosphonium bromide
  参考文献：
  名称：

  利用相转移介导的维蒂希烯化反应简捷高效地合成四氢喹啉生物碱

  摘要：

  本研究描述了分三个步骤，高收率合成1,2,3,4-四氢喹啉碱类生物碱（±）-半胱氨酸，（±）-cuspareine，（±）-半乳糖苷和（±）-Angustureine）（78分别从普通醛和叶立德中分离得到1％，76％，74％和66％）。此方法的关键步骤基于使用相转移介质（NaOH / CH 2 Cl 2 1：1水溶液或t -BuOK / t -BuOH / CH 2 Cl 2 1：1水溶液）进行的不寻常的Wittig反应，从而得到烯烃中间体的收率很高。

  DOI：

  10.1016/j.tetlet.2017.07.044

文献信息

• Synthesis of Unsymmetrical Linear Diarylheptanoids and their Enantiomers and Antiproliferative Activity Studies
  作者：Kasireddy Sudarshan、Govindaraj Perumal、Indrapal Singh Aidhen、Mukesh Doble

  DOI：10.1002/ejoc.201801211

  日期：2018.12.6

  A new route for the synthesis of unsymmetrical linear diarylheptanoids 1 and their enantiomers 2 via a common electrophilic intermediate 3 is presented using acyl anion chemistry and Wittig olefination. The cytotoxic activity of all the synthesized linear diarylheptanoids is tested.

  使用酰基阴离子化学和Wittig烯烃化反应，提出了一种通过常见的亲电子中间体3合成不对称线性二芳基庚烷类化合物1及其对映异构体2的新途径。测试所有合成的线性二芳基庚烷的细胞毒活性。
• Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction
  作者：Laura L. Taylor、Frederick W. Goldberg、King Kuok (Mimi) Hii

  DOI：10.1039/c2ob25122a

  日期：——

  An optically active tetrahydroquinoline intermediate (5) was prepared in 8 steps from monoprotected ethylene glycol, using a Pd-catalysed aza-Michael reaction to induce chirality. This can be transformed into three Galipea alkaloids (angustureine, galipeine and cuspareine). The proximity of a benzyloxy group is found to exert profound effects in several steps of the synthesis.

  一种光学活性的四氢喹啉中间体（5）经过8个步骤由单保护的乙二醇制备而成，使用钯催化的氮-迈克尔反应来引入手性。该中间体可以转化为三种Galipea生物碱（角度线碱、加利碱和库斯帕碱）。邻近的苄氧基团在合成的多个步骤中被发现对反应有显著影响。
• Antineoplastic agents. 166. Isolation, structure, and synthesis of combretastatin C-1
  作者：Sheo Bux Singh、George R. Pettit

  DOI：10.1021/jo00278a023

  日期：1989.8