triphenyl-(N-isobutylcarboxamidomethyl)-phosphonium bromide | 110890-35-2

• 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: triphenyl-(N-isobutylcarboxamidomethyl)-phosphonium bromide
• 英文别名: [2-[(2-methylpropyl)amino]-2-oxoethyl]triphenylphosphonium bromide；N-(2-methylpropyl)-2-triphenylphosphaniumylethanimidate;hydrobromide
• CAS: 110890-35-2
• 化学式: Br*C₂₄H₂₇NOP
• 分子量: 456.362
• InChiKey: WWGFEUXNDNLPHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  triphenyl-(N-isobutylcarboxamidomethyl)-phosphonium bromide 在 palladium diacetate lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 千日菊酰胺
  参考文献：
  名称：

  Efficient Preparation of Functionalized (E,Z) Dienes Using Acetylene as the Building Block

  摘要：

  DOI：

  10.1021/jo980440x
• 作为产物：
  描述：

  2-溴-n-异丁基乙酰胺 、 三苯基膦 以 苯 为溶剂， 反应 7.0h， 以86%的产率得到triphenyl-(N-isobutylcarboxamidomethyl)-phosphonium bromide
  参考文献：
  名称：

  使用有机钛试剂从醛立体选择性合成1,4-二取代的1,3-二烯

  摘要：

  由1-叔丁基硫代-3-三甲基甲硅烷基-1-丙烯生成的有机钛试剂与醛缩合，可通过（E）-赤藓基-单步合成1-叔丁硫基-（E，Z）-1,3-链二烯。 β-羟基硅烷具有高度区域选择性和立体选择性。在镍催化剂的存在下，通过与格氏试剂的交叉偶联反应，由二烯硫醚得到1，4-二烷基-1，3-二烯。该方法的实用性通过在五个步骤中应用于从蛇兰香中天然合成的杀虫剂斯皮兰特的合成中得到说明。

  DOI：

  10.1016/s0040-4020(01)90007-9

文献信息

• Bioavailability of Echinacea Constituents: Caco-2 Monolayers and Pharmacokinetics of the Alkylamides and Caffeic Acid Conjugates
  作者：A. Matthias、K. Penman、N. Matovic、K. Bone、J. De Voss、R. Lehmann

  DOI：10.3390/10101242

  日期：——

  Many studies have been done over the years to assess the effectiveness of Echinacea as an immunomodulator. We have assessed the potential bioavailability of alkyl- amides and caffeic acid conjugates using Caco-2 monolayers and compared it to their actual bioavailability in a Phase I clinical trial. The caffeic acid conjugates permeated poorly through the Caco-2 monolayers. Alkylamides were found to diffuse rapidly through Caco-2 monolayers. Differences in diffusion rates for each alkylamide correlated to structural variations, with saturation and N-terminal methylation contributing to decreases in diffusion rates. Alkylamide diffusion is not affected by the presence of other constituents and the results for a synthetic alkylamide were in line with those for alkylamides found in an ethanolic Echinacea preparation. We examined plasma from healthy volunteers for 12 hours after ingestion of Echinacea tablets manufactured from an ethanolic liquid extract. Caffeic acid conjugates could not be identified in any plasma sample at any time after tablet ingestion. Alkylamides were detected in plasma 20 minutes after tablet ingestion and for each alkylamide, pharmacokinetic profiles were devised. The data are consistent with the dosing regimen of one tablet three times daily and supports their usage as the primary markers for quality Echinacea preparations.

  多年来，已有许多研究对紫锥菊作为免疫调节剂的有效性进行了评估。我们使用 Caco-2 单层膜评估了烷基酰胺和咖啡酸共轭物的潜在生物利用度，并将其与 I 期临床试验中的实际生物利用度进行了比较。咖啡酸共轭物在 Caco-2 单层中的渗透性很差。烷基酰胺在 Caco-2 单层中的扩散速度很快。每种烷基酰胺的扩散速率差异与结构变化有关，饱和和 N 端甲基化导致扩散速率下降。烷基酰胺的扩散不受其他成分的影响，合成烷基酰胺的扩散结果与紫锥菊乙醇制剂中的烷基酰胺的扩散结果一致。我们检测了健康志愿者在服用由乙醇提取液制成的紫锥菊药片 12 小时后的血浆。在摄入片剂后的任何时间，任何血浆样本中都无法鉴定出咖啡酸共轭物。在服用片剂 20 分钟后的血浆中检测到烷基酰胺，并为每种烷基酰胺设计了药代动力学曲线。这些数据与每日三次、每次一片的用药方案一致，并支持将其作为优质紫锥菊制剂的主要标志物。
• Diacetylenic isobutylamides of Echinacea: synthesis and natural distribution
  作者：Lankun Wu、Jaehoon Bae、George Kraus、Eve Syrkin Wurtele

  DOI：10.1016/j.phytochem.2004.06.027

  日期：2004.9

  The syntheses of three diacetylenic isobutylamides of Echinacea angustifolia have been achieved by direct synthetic routes by way of a common intermediate. The key step is the alkylation of the anion of the silylated diacetylene. We report the presence of all three diacetylenic isobutylamides in six of the nine Echinacea species: E. angustifolia, E sanguinea, E. simulata, E. tennesseensis, E. atrorubens and E. laevigata. The accumulation of these amides is sensitive to organ type and age. (C) 2004 Elsevier Ltd. All rights reserved.
• Efficient Preparation of Functionalized (<i>E,Z</i>) Dienes Using Acetylene as the Building Block
  作者：Zhong Wang、Xiyan Lu、Aiwen Lei、Zhaoguo Zhang

  DOI：10.1021/jo980440x

  日期：1998.6.1
• Stereoselective synthesis of 1,4-disubstituted 1,3-diene from aldehyde using organotitanium reagent
  作者：Yoshihiko Ikeda、Junzo Ukai、Nobuo Ikeda、Hisashi Yamamoto

  DOI：10.1016/s0040-4020(01)90007-9

  日期：——

  Organotitanium reagent generated from 1-t-butylthio-3-trimethylsilyl-1-propene condenses with aldehydes to give 1 -t-butylthio-(E,Z)-1,3-alkadienes in a single step via (E)-erythro-β-hydroxysilane in a highly regio- and stereoselective manner. 1,4-Dialkyl-1,3-diene is obtaind from the diene sulfide by cross coupling reaction with Grignard reagent in the presence of nickel catalyst. The utility of the

  由1-叔丁基硫代-3-三甲基甲硅烷基-1-丙烯生成的有机钛试剂与醛缩合，可通过（E）-赤藓基-单步合成1-叔丁硫基-（E，Z）-1,3-链二烯。 β-羟基硅烷具有高度区域选择性和立体选择性。在镍催化剂的存在下，通过与格氏试剂的交叉偶联反应，由二烯硫醚得到1，4-二烷基-1，3-二烯。该方法的实用性通过在五个步骤中应用于从蛇兰香中天然合成的杀虫剂斯皮兰特的合成中得到说明。