(2'-methoxy-[1,1'-binaphthalen]-2-yl)diphenylphosphine oxide

• 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: (2'-methoxy-[1,1'-binaphthalen]-2-yl)diphenylphosphine oxide
• 英文别名: 1-(2-diphenylphosphorylnaphthalen-1-yl)-2-methoxynaphthalene
• 化学式: C₃₃H₂₅O₂P
• 分子量: 484.534
• InChiKey: OAUAPTQTUSEKHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2'-methoxy-[1,1'-binaphthalen]-2-yl)diphenylphosphine oxide 在 叔丁基锂 、 碘 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.2h， 以51%的产率得到2-(Diphenyl-phosphinoyl)-3-iodo-2'-methoxy-[1,1']binaphthalenyl
  参考文献：
  名称：

  Rhodium-Catalyzed Asymmetric Synthesis of Indanones:  Development of a New “Axially Chiral” Bisphosphine Ligand

  摘要：

  A rhodium-catalyzed asymmetric isomerization of racemic alpha-arylpropargyl alcohols to beta-chiral indanones has been developed. High enantioselectivity has been realized by the use of a newly developed axially chiral bisphosphine ligand. This ligand is unique in the sense that its axial chirality is fixed to a single configuration upon complexation to a transition metal due to other chiral axes existing within the same molecule.

  DOI：

  10.1021/ja056584s
• 作为产物：
  描述：

  (R)-2-羟基-2’-甲氧基-1,1’-联萘 在 吡啶 、 palladium diacetate 、 三乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 17.0h， 生成 (2'-methoxy-[1,1'-binaphthalen]-2-yl)diphenylphosphine oxide
  参考文献：
  名称：

  New Route for Synthesis of MeO-MOP

  摘要：

  The axially chiral monophosphine 2-(diphenylphosphino)-2 '-methoxy-1,1 '-binaphthyl (MeO-MOP) is a versatile ligand. We report a shorter (four steps from chiral BINOL), more atom-economical synthetic route to MeO-MOP. (R)-BINOL is transformed into its monomethyl ether by the Mitsunobu reaction, and the latter is reacted with triflic anhydride to give its triflate. The C-P coupling of the triflate and diphenylphosphine oxide catalyzed by palladium give a phosphine oxide, the precursor of (R)-MeO-MOP, which is reduced with trichlorosilane to furnish (R)-MeO-MOP.

  DOI：

  10.1080/00397911.2010.519095

文献信息

• Iridium(III)-Catalyzed CH Amidation of Arylphosphoryls Leading to a<i>P</i>-Stereogenic Center
  作者：Donghyeon Gwon、Donggun Lee、Jiyu Kim、Sehoon Park、Sukbok Chang

  DOI：10.1002/chem.201404151

  日期：2014.9.22

  Direct CH amidation of arylphosphoryl compounds has been developed by using an IrIII catalyst system under mild conditions. A wide range of substrates could be employed with high functional‐group tolerance. This procedure was successfully applied for the first time to the asymmetric reaction giving rise to a P‐chirogenic center with a high diastereomeric ratio of up to 19:1 (90 % de).

  直销Ç  ħ芳基磷化合物的酰胺化已经通过使用IR开发III温和的条件下的催化剂体系。可以使用具有高官能团耐受性的各种基材。该方法首次成功地用于不对称反应，生成了一个P-色原中心，其非对映异构体的比例高达19：1（90％  de）。
• A Mild One-Pot Reduction of Phosphine(V) Oxides Affording Phosphines(III) and Their Metal Catalysts
  作者：Łukasz Kapuśniak、Philipp N. Plessow、Damian Trzybiński、Krzysztof Woźniak、Peter Hofmann、Phillip Iain Jolly

  DOI：10.1021/acs.organomet.0c00788

  日期：2021.3.22

  metal-free reduction of a range of phosphine(V) oxides employing oxalyl chloride as an activating agent and hexachlorodisilane as reducing reagent has been achieved under mild reaction conditions. The method was successfully applied to the reduction of industrial waste byproduct triphenylphosphine(V) oxide, closing the phosphorus cycle to cleanly regenerate triphenylphosphine(III). Mechanistic studies and quantum

  在温和的反应条件下，已经实现了使用草酰氯作为活化剂和六氯乙硅烷作为还原剂的一系列膦（V）氧化物的无金属还原。该方法成功地用于减少工业废物副产物三苯基膦（V）的氧化，关闭磷循环以干净地再生三苯基膦（III）。机理研究和量子化学计算支持中间体phospho盐的离解氯离子对乙硅烷硅的攻击，这是脱保护的限速步骤。
• Palladium-catalyzed R₂(O)P directed C(sp²)–H acetoxylation
  作者：Heng Zhang、Rong-Bin Hu、Xiao-Yu Zhang、Shi-Xia Li、Shang-Dong Yang

  DOI：10.1039/c4cc01238k

  日期：——

  A novel and efficient Pd-catalyzed C–H acetoxylation is described. The approach uses R₂(O)P as a directing group to synthesize various substituted 2′-phosphoryl biphenyl-2-OAc compounds.

  描述了一种新颖高效的钯催化的C-H乙酰化方法。该方法使用R₂(O)P作为导向基团，合成各种取代的2'-磷酸酯联苯-2-OAc化合物。
• Axially Chiral Biaryl Monophosphine Oxides Enabled by Palladium/WJ-Phos-Catalyzed Asymmetric Suzuki–Miyaura Cross-coupling
  作者：Wangqin Ji、Hai-Hong Wu、Junliang Zhang

  DOI：10.1021/acscatal.9b04354

  日期：2020.1.17

  palladium/WJ-Phos-catalyzed Suzuki–Miyaura coupling reaction for efficient construction of axially chiral biaryl monophosphine oxides was developed. A series of axially chiral biaryl monophosphine oxides were obtained in good yields and with high enantioselectivities. The practicability of this reaction was validated in the straightforward synthesis of axially chiral biaryl monophosphine ligand and demonstrated

  开发了一种高对映选择性的钯/ WJ-Phos催化的Suzuki-Miyaura偶联反应，可有效构建轴向手性联芳基单膦氧化物。以高收率和高对映选择性获得了一系列轴向手性联芳基单膦氧化物。该反应的实用性在轴向手性联芳基单膦配体的直接合成中得到验证，并通过100 g规模的合成得到证明。此外，产物的各种官能化使其成为合成其他手性联芳基膦的平台分子。
• Nucleophilic Aromatic Substitution Reactions of 1-Methoxy-2-(diphenylphosphinyl)naphthalene with<i>C</i>-,<i>N</i>-, and<i>O</i>-Nucleophiles: Facile Synthesis of Diphenyl(1-substituted-2-naphthyl)phosphines
  作者：Tetsutaro Hattori、Jun'ichi Sakamoto、Noriyuki Hayashizaka、Sotaro Miyano

  DOI：10.1055/s-1994-25438

  日期：——

  A novel nucleophilic aromatic substitution reaction is described in which the methoxy group of 1-methoxy-2-(diphenylphosphinyl)-naphthalene is readily replaced with Grignard reagents, alkoxides, and amides. Reduction of the resulting phosphine oxides provides a convenient route to diphenyl(1-substituted-2-naphthyl)phosphines.

  描述了一种新型亲核芳族取代反应，其中 1-甲氧基-2-(二苯基次膦基)-萘的甲氧基很容易被格氏试剂、醇盐和酰胺取代。所得氧化膦的还原提供了制备二苯基(1-取代-2-萘基)膦的便捷途径。