<3-(4-Methoxyphenyl)-2-propenyl>triphenylphosphoniumbromid | 138958-72-2

• 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-(4-Methoxyphenyl)-2-propenyl>triphenylphosphoniumbromid
• 英文别名: [3-(4-Methoxyphenyl)-2-propenyl]triphenylphosphoniumbromid
• CAS: 138958-72-2
• 化学式: Br*C₂₈H₂₆OP
• 分子量: 489.392
• InChiKey: HFTBXHJQJQHREE-CALJPSDSSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  <3-(4-Methoxyphenyl)-2-propenyl>triphenylphosphoniumbromid 在 正丁基锂 、 sodium methylate 作用下， 以 甲醇 、 xylene 为溶剂， 反应 1.0h， 生成 (1S,8R,9S)-9-(4-Methoxy-phenyl)-12-aza-tricyclo[6.3.2.0^2,7]trideca-2,4,6,10,12-pentaene-13-carboxylic acid methyl ester
  参考文献：
  名称：

  α-叠氮吲哚与4-取代的1,3-二烯的分子内反应

  摘要：

  据报道，新的8,9-苯并-6-氮杂双环[3.2.2] nona-3,6,8-三烯14通过分子内的α-叠氮吲哚9与烷基和苯基取代的邻丁二烯基侧链反应合成，以及新的1-氮杂-2-碳甲氧基-7,8-苯并三环[4.30.0 2,9 ]壬娜-4,7-二烯15的形成。

  DOI：

  10.1016/0040-4039(91)80343-5
• 作为产物：
  描述：

  (2E)-3-(4-甲氧基苯基)-2-丙烯-1-醇 在 氢溴酸 作用下， 以 乙醚 、 溶剂黄146 、 苯 为溶剂， 反应 16.25h， 生成 <3-(4-Methoxyphenyl)-2-propenyl>triphenylphosphoniumbromid
  参考文献：
  名称：

  Eberbach, Wolfgang; Trostmann, Uwe, Chemische Berichte, 1981, vol. 114, # 9, p. 2979 - 3003

  摘要：

  DOI：

文献信息

• Alcohols as Efficient Intermolecular Initiators for a Highly Stereoselective Polyene Cyclisation Cascade
  作者：Daniya Aynetdinova、Reece Jacques、Kirsten E. Christensen、Timothy J. Donohoe

  DOI：10.1002/chem.202203732

  日期：2023.3

  A stereoselective polyene cyclisation cascade was enabled by using HFIP as a solvent. The process is triggered by a cation generated from an alcohol in situ and leads to the formation of three new C-C bonds and up to five new stereocenters as a single diastereomer. The cyclised products can be derivatised to obtain steroidal analogues in a single step.

  通过使用 HFIP 作为溶剂实现立体选择性多烯环化级联反应。该过程由醇原位产生的阳离子触发，并导致形成三个新的 C-C 键和多达五个新的立体中心作为单个非对映异构体。环化产物可以衍生化，一步获得甾体类似物。
• 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
  作者：Zelleka Getahun、Leonard Jurd、Ping S. Chu、Chii M. Lin、Ernest Hamel

  DOI：10.1021/jm00084a011

  日期：1992.3

  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).