bis-(p-methoxybenzyl) tartrate | 64370-69-0

• 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: bis-(p-methoxybenzyl) tartrate
• 英文别名: Bis[(4-methoxyphenyl)methyl] 2,3-dihydroxybutanedioate
• CAS: 64370-69-0；138515-24-9
• 化学式: C₂₀H₂₂O₈
• 分子量: 390.39
• InChiKey: YRLYXFBOMQAATC-UHFFFAOYSA-N

物化性质

• 沸点：
  544.6±45.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  bis-(p-methoxybenzyl) tartrate 在 lead(IV) acetate 作用下， 以 苯 为溶剂， 反应 1.5h， 以95%的产率得到p-methoxybenzyl glyoxylate monohydrate
  参考文献：
  名称：

  Synthesis of 6-(substituted methylene) carbapenem derivatives from 6-aminopenicillanic acid

  摘要：

  The key intermediate in the preparation of novel 6-(substituted methylene) carbapenem derivatives is p-methoxybenzyl (5R,6R)-6-bromo-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 26, which was prepared in several steps from 6-aminopenicillanic acid 14 via (3R,4R)-4-allyl-3-bromoazetidin-2-one 21. Sequential treatment of the aforementioned ester 26 with either lithium diisopropylamide or lithium diphenylamide, 1-methyl-1H-1,2,3-triazole-4-carbaldehyde and acetic anhydride provided a diastereoisomeric mixture of acylated bromohydrins 28; reductive elimination then afforded the isomeric (E)- and (Z)-6-triazolylmethylene carbapenem esters 29 and 31, respectively. Lewis acid-mediated deprotection of the 6-bromo and 6-[(E)-triazolylmethylene] esters 26 and 29 gave the sodium salts of (5R,6R)-6-bromo-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 27 and (5R)-6-[(E)-(1-methyl-1H-1,2,3-triazol-4-yl)methylene]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 30, respectively.In addition, condensation of the anion, generated by deprotonation of the 6-bromo ester, with acetaldehyde, followed by acylation and reductive elimination furnished the isomeric (E)- and (Z)-ethylidene carbapenem esters.Whilst the (E)-6-triazolylmethylene carbapenem displayed low levels of antibacterial activity, it possessed no beta-lactamase-inhibitory activity whatsoever. The 6-bromocarbapenem was devoid of both antibacterial and beta-lactamase-inhibitory activity.

  DOI：

  10.1039/p19910002699
• 作为产物：
  描述：

  4-甲氧基苄醇 在 三溴化磷 、 三乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 bis-(p-methoxybenzyl) tartrate
  参考文献：
  名称：

  Synthesis of 6-(substituted methylene) carbapenem derivatives from 6-aminopenicillanic acid

  摘要：

  The key intermediate in the preparation of novel 6-(substituted methylene) carbapenem derivatives is p-methoxybenzyl (5R,6R)-6-bromo-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 26, which was prepared in several steps from 6-aminopenicillanic acid 14 via (3R,4R)-4-allyl-3-bromoazetidin-2-one 21. Sequential treatment of the aforementioned ester 26 with either lithium diisopropylamide or lithium diphenylamide, 1-methyl-1H-1,2,3-triazole-4-carbaldehyde and acetic anhydride provided a diastereoisomeric mixture of acylated bromohydrins 28; reductive elimination then afforded the isomeric (E)- and (Z)-6-triazolylmethylene carbapenem esters 29 and 31, respectively. Lewis acid-mediated deprotection of the 6-bromo and 6-[(E)-triazolylmethylene] esters 26 and 29 gave the sodium salts of (5R,6R)-6-bromo-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 27 and (5R)-6-[(E)-(1-methyl-1H-1,2,3-triazol-4-yl)methylene]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 30, respectively.In addition, condensation of the anion, generated by deprotonation of the 6-bromo ester, with acetaldehyde, followed by acylation and reductive elimination furnished the isomeric (E)- and (Z)-ethylidene carbapenem esters.Whilst the (E)-6-triazolylmethylene carbapenem displayed low levels of antibacterial activity, it possessed no beta-lactamase-inhibitory activity whatsoever. The 6-bromocarbapenem was devoid of both antibacterial and beta-lactamase-inhibitory activity.

  DOI：

  10.1039/p19910002699

文献信息

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  申请人：XEROX CORPORATION

  公开号：US20140083325A1

  公开（公告）日：2014-03-27

  A phase change ink including an amorphous compound; a crystalline compound; an optional colorant; an optional synergist; an optional dispersant; and at least one polyhydroxyalkanoate compound of the formula wherein R is independently selected from the group consisting of a hydrogen atom, a hydrocarbon group, a heteroatom, and combinations thereof; wherein n represents the number of repeating units of from 1 to about 35,000; and wherein x represents an integer from 1 to about 5.
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  公开号：US20140118436A1

  公开（公告）日：2014-05-01

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  申请人：XEROX CORPORATION

  公开号：US20140287205A1

  公开（公告）日：2014-09-25

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  公开（公告）日：2014-12-18

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• Phase Change Ink Containing Amorphous Amides
  申请人：Xerox Corporation

  公开号：US20150103122A1

  公开（公告）日：2015-04-16

  A phase change ink composition comprising an amorphous amide compound, a crystalline compound; an optional synergist; an optional dispersant; and an optional colorant; wherein the amorphous amide compound is of the formula wherein R is selected from the group consisting of an alkyl group, an aryl group, an alkylaryl group, an arylalkyl group, and combinations thereof, or wherein the amorphous amide compound is of the formula wherein R 1 is selected from the group consisting of an alkylene group, an arylene group, an alkylarylene group, an arylalkylene group, and combinations thereof.