adamantylhydrogeno(tert-butyl)phosphinate | 1619925-51-7

• 分子结构分类: 有机化合物
• 英文名称: adamantylhydrogeno(tert-butyl)phosphinate
• 英文别名: 1-[Tert-butyl(oxido)phosphaniumyl]oxyadamantane
• CAS: 1619925-51-7
• 化学式: C₁₄H₂₅O₂P
• 分子量: 256.325
• InChiKey: QBNNUPAYBFVCMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  adamantylhydrogeno(tert-butyl)phosphinate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 正己烷 、 水 、 异丙醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  H-Adamantylphosphinates as Universal Precursors of P-Stereogenic Compounds

  摘要：

  A new family of H-adamantylphosphinates as universal precursors of P-stereogenic ligands was obtained in one step from commercial chlorophosphines. Both enantiomers of these air- and moisture-stable intermediates can easily be separated by semipreparative chiral HPLC on a gram scale and individually undergo stereoselective transformations to afford each enantiomer of a set of P-stereogenic compounds such as secondary phosphine oxides and boron-protected monophosphines.

  DOI：

  10.1021/acs.joc.5b00548
• 作为产物：
  描述：

  1-金刚烷醇 在 三氯化磷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 adamantylhydrogeno(tert-butyl)phosphinate
  参考文献：
  名称：

  H-Adamantylphosphinates as Universal Precursors of P-Stereogenic Compounds

  摘要：

  A new family of H-adamantylphosphinates as universal precursors of P-stereogenic ligands was obtained in one step from commercial chlorophosphines. Both enantiomers of these air- and moisture-stable intermediates can easily be separated by semipreparative chiral HPLC on a gram scale and individually undergo stereoselective transformations to afford each enantiomer of a set of P-stereogenic compounds such as secondary phosphine oxides and boron-protected monophosphines.

  DOI：

  10.1021/acs.joc.5b00548

文献信息

• [EN] P-STEREOGENIC CHIRAL PRECURSOR OF CHIRAL LIGANDS AND USE THEREOF<br/>[FR] PRÉCURSEUR CHIRAL P-STÉRÉOGÈNE DE LIGANDS CHIRAUX ET SON UTILISATION
  申请人：UNIV AIX MARSEILLE

  公开号：WO2014108487A1

  公开（公告）日：2014-07-17

  The present invention concerns phosphinate universal P-stereogenic chiral precursors of formula (I) for chiral ligands, preparation processes thereof and their use for the preparation of optically pure or enriched chiral ligands. Claimed are formula (I) compounds as stereoisomer, preferably enantiomer: (I) RO is a tertiary alkoxy group comprising at least 5 carbon atoms, R' is chosen in the group consisting of alkyl, alkenyl, alkynyl, heteroaryl and aryl groups, Examples for one of the claimed processes is: (II) An example for the use of such phosphinates to make other P- stereogenic ligands is (Ad means adamantyl): (III).

  本发明涉及磷酸盐通用P-立体化手性前体的化学式(I)用于手性配体，其制备方法以及用于制备光学纯或富集手性配体的用途。所述的化学式(I)化合物作为立体异构体，优选对映体：(I)中，RO是含有至少5个碳原子的三级烷氧基团，R'选择自烷基、烯基、炔基、杂环烷基和芳基组成的群中。所述过程的一个示例是：(II)。使用这种磷酸盐制备其他P-立体化配体的一个示例是(Ad代表壳烷基)：(III)。
• Synthesis of chiral supramolecular bisphosphinite palladacycles through hydrogen transfer-promoted self-assembly process
  作者：Alexandre Vasseur、Romain Membrat、Davide Palpacelli、Michel Giorgi、Didier Nuel、Laurent Giordano、Alexandre Martinez

  DOI：10.1039/c8cc06283h

  日期：——

  P-Chiral secondary phosphine oxides react with Pd₂(dba)₃ in an acidic medium to provide chiral supramolecular bisphosphinite palladacycles through a H-transfer-based self-assembly process prior to SPO-promoted oxidative addition of an acid to a Pd(0) centre.

  P-手性二次膦氧化物在酸性介质中与Pd2(dba)3反应，通过基于氢转移的自组装过程，形成手性超分子双膦酰基钯环，然后在SPO促进下将酸氧化加到Pd(0)中心。