Dimethoxymethyldiphenylphosphine oxide | 86658-86-8

• 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: Dimethoxymethyldiphenylphosphine oxide
• 英文别名: dimethoxymethyl phosphine oxide；(dimethoxymethyl)diphenylphosphane oxide；Dimethoxymethyl diphenyl phosphine oxide；[dimethoxymethyl(phenyl)phosphoryl]benzene
• CAS: 86658-86-8
• 化学式: C₁₅H₁₇O₃P
• 分子量: 276.272
• InChiKey: SIAHMWSAGVMVDK-UHFFFAOYSA-N

物化性质

• 沸点：
  351.5±32.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Dimethoxymethyldiphenylphosphine oxide 在 盐酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Diphenylphosphine oxide
  参考文献：
  名称：

  烷基卤化物和氨基醛与基于氧化膦的 d1-Synthon 的酰化

  摘要：

  使用锂化（二甲氧基甲基）二苯基膦氧化物，烷基碘和 α-氨基醛可以与相应的甲酯和 β-氨基甲酯（包括 β-氨基-α-羟基甲酯）同系。通过这种 Horner-Wittig 型方法获得的主要 α,α-（二甲氧基）二苯基膦氧化物在质子催化条件下在水存在下崩溃以产生目标酯。详细且仔细进行的机理研究表明，二苯基氧化膦基团被质子化激活，并作为该过程中的初始离去基团。在由氧化膦稳定的阴离子与 α-氨基醛反应衍生的加合物的情况下，可以通过 KOtBu 介导的消除中间体来实现与 β-氨基-和 β-氨基-α-羟基甲酯的同系化O,O-烯酮缩醛。它们可以在酸性条件下与水反应以产生 β-氨基甲酯，或者可以在 Sharpless 不对称二羟基化条件下处理以直接提供 β-氨基-α-羟基甲酯。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200300631
• 作为产物：
  描述：

  二苯基氯化膦 、 原甲酸三甲酯 反应 2.0h， 以83%的产率得到Dimethoxymethyldiphenylphosphine oxide
  参考文献：
  名称：

  Asymmetric Nucleophilic Acylation of Aldehydes via 1,1-Heterodisubstituted Alkenes

  摘要：

  Aldehydes are asymmetrically acylated by a two step sequence that is initiated by a homologation step to 1,1-heterodisubstituted alkenes followed by asymmetric dihydroxylation. Thus, ketene O,S-acetals are efficiently prepared from aldehydes by a Peterson olefination with lithiated methoxy-phenylthiotrimethylsilyl methane 14 as the C-1 source. Although they are dihydroxylated with the Sharpless catalyst with moderate to good enantioselectivity (62-80% ee), the process is not efficient owing to the low chemical yields of the desired alpha-hydroxy methyl esters (7-37%). Use of the corresponding sulfoxide 24 or sulfon 25 led to an improved chemical yield of alpha-hydroxy methyl ester 19, but the stereoselectivity was diminished. In contrast, intermediate ketene O,O-acetals are prepared by a Horner-Wittig reaction with phosphine oxide 31 and are dihydroxylated both with good chemical and stereochemical yield. The concept is applicable to aromatic, aliphatic, and chiral aldehydes. For example, this short sequence allows exclusive and independent preparation of both diastereomeric heptoses 69a and 69b.

  DOI：

  10.1002/(sici)1521-3765(19990802)5:8<2270::aid-chem2270>3.0.co;2-l

文献信息

• A Horner-Wittig solution to the synthesis of ketene, O,O-acetals.
  作者：T.A.M. van Schaik、A.V. Henzen、A. van der Gen

  DOI：10.1016/s0040-4039(00)81641-x

  日期：1983.1

  Aldehydes as well as ketones can be converted into their homologous ketene, O-O-acetals by a Horner-Wittig reaction with dialkoxymethyl diphenylphosphine oxides.

  醛和酮可以通过与二烷氧基甲基二苯基膦氧化物的霍纳-威蒂希反应转化为它们的同源烯酮OO-乙缩醛。
• Lithiated Dimethoxymethyl Diphenyl Phosphine Oxide, A Versatile Formiate Carbanion Equivalent
  作者：Holger Monenschein、Marco Brünjes、Andreas Kirschning

  DOI：10.1055/s-2002-20486

  日期：——

  Aldehydes are homologated to the corresponding α-hydroxy methyl esters using lithiated dimethoxymethyl diphenyl phosphine oxide. The primary addition product of this Horner-Wittig process collapses to the corresponding α-hydroxy ester under proton-catalyzed conditions.

  使用锂化的二甲氧基甲基二苯基膦氧化物将醛类同系为相应的 α-羟基甲酯。在质子催化条件下，该 Horner-Wittig 过程的主要加成产物分解为相应的 α-羟基酯。
• Methods of using piperazine derivatives
  申请人：Pfizer Inc

  公开号：US20040092529A1

  公开（公告）日：2004-05-13

  The present invention relates to compounds of the formula I 1 and the pharmaceutically acceptable forms thereof; wherein X, Y, a, b, c, d, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein. Moreover, the present invention is also directed at pharmaceutical compositions comprising a compound of the formula I and a pharmaceutically acceptable carrier. Furthermore, the present invention is directed at methods of using the herein described compounds and compositions for treating or preventing a disorder or condition that can be treated or prevented by antagonizing the CCR1 receptor in a mammal.

  本发明涉及公式I1的化合物及其药学上可接受的形式；其中X、Y、a、b、c、d、R1、R2、R3、R4和R5如本文所定义。此外，本发明还涉及包含公式I的化合物和药学上可接受的载体的药物组合物。此外，本发明还涉及使用本文所述的化合物和组合物治疗或预防哺乳动物中可通过拮抗CCR1受体治疗或预防的疾病或状况的方法。
• Towards the total synthesis of tonantzitlolone––preparation of key fragments and the complete carbon backbone
  作者：Rüdiger Wittenberg、Christian Beier、Gerald Dräger、Gerhard Jas、Christian Jasper、Holger Monenschein、Andreas Kirschning

  DOI：10.1016/j.tetlet.2004.04.056

  日期：2004.5

  The first synthetic advances towards the novel diterpenoid tonantzitlolone 1 are described. The key steps in the synthesis involve a chromium(II) Reformatsky reaction, a diastereoselective C1 extension and an expeditious aldol coupling step of two advanced precursors.

  描述了向新颖的二萜类坦西隆1的第一个合成进展。合成中的关键步骤涉及铬（II）Reformatsky反应，非对映选择性C 1延伸和两个高级前体的快速羟醛偶联步骤。
• Novel piperazine derivatives
  申请人：——

  公开号：US20040034034A1

  公开（公告）日：2004-02-19

  The present invention relates to compounds of the formula I 1 and the pharmaceutically acceptable forms thereof; wherein X, Y, a, b, c, d, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein. Moreover, the present invention is also directed at pharmaceutical compositions comprising a compound of the formula I and a pharmaceutically acceptable carrier. Furthermore, the present invention is directed at methods of using the herein described compounds and compositions for treating or preventing a disorder or condition that can be treated or prevented by antagonizing the CCR1 receptor in a mammal.

  本发明涉及公式I1的化合物及其药学上可接受的形式；其中X、Y、a、b、c、d、R1、R2、R3、R4和R5的定义如本文所述。此外，本发明还涉及包含公式I的化合物和药学上可接受的载体的制药组合物。此外，本发明还涉及使用上述化合物和组合物治疗或预防哺乳动物中可以通过拮抗CCR1受体来治疗或预防的疾病或症状的方法。