tetraphenylphosphonium monoperoxysulfate

• 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: tetraphenylphosphonium monoperoxysulfate
• 英文别名: tetraphenylphosphonium monopersulphate；tetraphenylphosphonium peroxymonosulfate；TPPP；hydroxy sulfate;tetraphenylphosphanium
• 化学式: C₂₄H₂₀P*HO₅S
• 分子量: 452.468
• InChiKey: NAMHVGGLAWOQPP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  四苯基氯化膦 在 potassium sulfate 、 potassium hydrogensulfate 、 oxone 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以70%的产率得到tetraphenylphosphonium monoperoxysulfate
  参考文献：
  名称：

  非水亚胺盐介导的催化不对称环氧化

  摘要：

  使用我们新开发的非水条件，使用四苯基phosph单过氧硫酸盐（TPPP）作为氧化剂，已经在简单烯烃的催化不对称环氧化中测试了一系列取代的二氢异喹啉鎓盐，其ee最高可达97％。

  DOI：

  10.1016/j.tet.2005.10.084
• 作为试剂：
  描述：

  1-丙烯基苯 在 (+)-N-((4S,5S)-2,2-dimethyl-4-(4-(methylsulfonyl)phenyl)-1,3-dioxan-5-yl)-3,4-dihydroisoquinolinium tetraphenylborate tetraphenylphosphonium monoperoxysulfate 作用下， 以 氯仿 为溶剂， 反应 24.33h， 以85%的产率得到2-甲基-3-苯基环氧乙烷
  参考文献：
  名称：

  [EN] PROCESS FOR USE IN THE PREPARATION OF OXIRANES FROM ALKENES, AND CATALYSTS FOR USE THEREIN
  [FR] PROCEDE DESTINE A ETRE UTILISE DANS LA PREPARATION D'OXYRANES A PARTIR D'ALCENES ET CATALYSEURS UTILISES A CET EFFET

  摘要：

  公开号：

  WO2005056543A3

文献信息

• Asymmetric epoxidation of chromenes mediated by iminium salts: Synthesis of mollugin and (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin
  作者：Philip C. Bulman Page、Yohan Chan、Abu Hassan Noor Armylisas、Mohammed Alahmdi

  DOI：10.1016/j.tet.2016.10.070

  日期：2016.12

  Organocatalytic asymmetric epoxidation of chromenes mediated by iminium salt catalysts under non-aqueous conditions provided ees as high as 99%. Contrastingly, reaction under aqueous conditions can form the corresponding diol products with ees as high as 71%. The process has been used for the synthesis of the East African medicinal plant metabolite (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin.

  亚胺盐催化剂在非水条件下介导的色酮的有机催化不对称环氧化提供了高达99％的ee。相反，在水性条件下的反应可以形成相应的二醇产物，其ee s高达71％。该方法已用于合成东非药用植物代谢产物（3 S，4 R）-反式-3,4-二羟基-3,4-二氢软糖。
• Towards heterogeneous organocatalysis: chiral iminium cations supported on porous materials for enantioselective alkene epoxidation
  作者：Philip C. Bulman Page、Andrew Mace、Damien Arquier、Donald Bethell、Benjamin R. Buckley、David J. Willock、Graham J. Hutchings

  DOI：10.1039/c3cy00352c

  日期：——

  Enantiomerically pure iminium cations have been supported on a microporous support (zeolite Y) and on a mesoporous support (Al-MCM-41). These materials are effective asymmetric catalysts for the epoxidation of a range of aryl alkenes, giving high conversions quickly and with enantioselectivities similar to or in some cases even higher than are achievable using the corresponding iminium tetraphenylborates under homogeneous conditions. The catalysts can be simply recycled by filtration and washing. The methodology is illustrated in the synthesis of two natural products, (−)-(3′S)-lomatin and (+)-(3′S,4′R)-trans-khellactone, showing the general efficacy of our approach.

  对映体纯亚胺阳离子被支持在微孔支持物（沸石 Y）和介孔支持物（Al-MCM-41）上。这些材料是一系列芳基烯烃环氧化反应的有效不对称催化剂，可快速实现高转化率，其对映体选择性与在均相条件下使用相应的四苯基硼酸亚胺所实现的对映体选择性相似，在某些情况下甚至更高。催化剂只需过滤和洗涤即可循环使用。该方法通过合成两种天然产物--(-)-(3′S)-洛马汀和(+)-(3′S,4′R)-反式黄柏内酯进行了说明，显示了我们方法的普遍有效性。
• Synthesis and X-Ray Crystal Structure of the First Pure and Air-Stable Salt of Peroxymonosulphuric Acid: (Ph)4PHSO5
  作者：Sandro Campestrini、Marco Crisma

  DOI：10.3390/50600886

  日期：——

  In this paper we describe the synthesis of tetraphenylphosphonium peroxymonosulphate, its crystal structure and packing mode. The asymmetric unit accomodates two independent molecules of the monopersulphate anion, which are held together by hydrogen bonds. In the packing mode, rows of such dimers are surrounded by four rows of tetraphenyl cations. The consequence is that the highly water sensitive HSO5¯ anions are segregated inside hydrophobic channels composed by the lipophilic cations. This circumstance presumably accounts for the exceptional stability of the title compound.

  本文介绍了过一硫酸四苯基膦的合成、晶体结构和堆积模式。不对称单元容纳了两个独立的单过硫酸根阴离子分子，它们通过氢键结合在一起。在堆积模式中，一排排这样的二聚体被四排四苯基阳离子包围。因此，对水高度敏感的 HSO5'阴离子被隔离在由亲油阳离子组成的疏水通道内。这种情况大概就是标题化合物具有超强稳定性的原因。
• Asymmetric Epoxidation of <i>cis</i>-Alkenes Mediated by Iminium Salts:  Highly Enantioselective Synthesis of Levcromakalim
  作者：Philip C. Bulman Page、Benjamin R. Buckley、Harry Heaney、A. John Blacker

  DOI：10.1021/ol047836h

  日期：2005.2.1

  A range of cis-substituted olefins has been epoxidized with a new dihydroisoquinolinium salt catalyst, using tetraphenylphosphonium monoperoxysulfate as the stoichiometric oxidant, giving ee's of up to 97%. The reaction has been used as the key step in an enantioselertive synthesis of the antihypertensive agent levcromakalim.