1,4-bis(diphenylphosphinoyl)buta-1,3-diyne | 191597-85-0

• 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: 1,4-bis(diphenylphosphinoyl)buta-1,3-diyne
• 英文别名: bis(diphenylphosphinyl)butadiyne；[4-Diphenylphosphorylbuta-1,3-diynyl(phenyl)phosphoryl]benzene
• CAS: 191597-85-0
• 化学式: C₂₈H₂₀O₂P₂
• 分子量: 450.413
• InChiKey: PRBPITUIEMTOEL-UHFFFAOYSA-N

物化性质

• 沸点：
  606.9±38.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-bis(diphenylphosphinoyl)buta-1,3-diyne 在 盐酸 、 silver tetrafluoroborate 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 生成
  参考文献：
  名称：

  Stereodynamic tetrahydrobiisoindole “NU-BIPHEP(O)”s: functionalization, rotational barriers and non-covalent interactions

  摘要：

  立体动力学配体在对映选择性催化中提供了有趣的可能性。“NU-BIPHEPs”是一类立体动力学二膦配体，可通过铑催化的双[2+2+2]环加成反应轻松获得。本研究探讨了不同官能团的“NU-BIPHEP(O)”化合物的制备、非共价加合物形成的表征以及旋转异构化壁垒的定量。为了探索官能团化的可能性，我们研究了配体骨架的修饰，例如使用3,5-二氯苯甲酰氯。基于非共价相互作用，实现了与岡本型纤维素衍生物的非对映异构体加合物和柱上去对映异构化。对映选择性动态高效液相色谱（DHPLC）可确定“NU-BIPHEPs”和“NU-BIPHEP(O)s”的旋转壁垒分别为ΔG^‡_298K = 92.2 ± 0.3 kJ mol⁻¹和99.5 ± 0.1 kJ mol⁻¹，强调了它们的立体动力学性质。这些结果使得定制官能团化的立体动力学配体的制备成为可能，并为在对映选择性催化中的应用提供了概述。

  DOI：

  10.3762/bjoc.12.141
• 作为产物：
  描述：

  1,3-bis(diphenylphosphino)buta-1,3-diyne 在 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以98%的产率得到1,4-bis(diphenylphosphinoyl)buta-1,3-diyne
  参考文献：
  名称：

  铑催化的1，4-双（二苯基膦酰基）buta-1,3-diyne与束缚二炔的双[2 + 2 + 2]环加成反应：NU-BIPHEP双芳基二膦酸酯的模块化，高度通用的单罐合成。

  摘要：

  铑催化的1,4-双（二苯基膦酰基）丁1,3-二炔与束缚二炔的双[2 + 2 + 2]环加成反应为合成新型对位联芳基二膦提供了一种简单的单釜法，NU-BIPHEP。这种方法代表了对现有多步骤程序的重大改进。这些二膦的对映纯路易斯酸铂络合物是羰基-烯和Diels-Alder反应的高效催化剂，钌二膦二胺络合物催化酮的不对称还原，得到的ee可以与用BINAP对应的ee竞争。

  DOI：

  10.1021/ol702390p

文献信息

• [EN] BIARYL DIPHOSPHINES<br/>[FR] BIARYLDIPHOSPHINES
  申请人：UNIV NEWCASTLE

  公开号：WO2009044130A1

  公开（公告）日：2009-04-09

  A compound of formula (I):wherein: X is selected from O, S, NRN1, PRP1, SiRSi1RSi2, BRB1, CRC1RC2 and (CRC1RC2)2,, where RN1 is selected from H, C1-7 alkyl sulfonyl, benzyl and C1-7 alkyl, RP1 is selected from C1-7 alkyl and C5-7 aryl, RSi1 and RSi2 are independently selected from H, C1-7 alkyl, benzyl and C5-7 aryl, RB1 is selected from C1-7 alkyl, C5-7 aryl, C1-7 alkyloxy, C5-7 aryloxy, and RC1 and RC2 are independently selected from H, C1-7 alkyl, and C1-7 alkylester; if X is (CRC1RC2)2 then, the two carbon atoms may form part of a fused carbocyclic or heterocyclic ring, having between 3 and 7 ring atoms; R1 is selected from H, hydroxy, C1-7 alkyl, C1-7 alkyloxy, silyloxy, C1-7 alkylester; R2 is selected from H, hydroxy, C1-7 alkyl, C1-7 alkyloxy, silyloxy, C1-7 alkylester; and RP is selected from C5-20 aryl, di(C1-7 alkyl) amino, C1-7 alkoxy, chloro and C1-7 alkyl.

  式(I)的化合物：其中：X选自O、S、NRN1、PRP1、SiRSi1RSi2、BRB1、CRC1RC2和(CRC1RC2)2，其中RN1选自H、C1-7烷基磺酰基、苄基和C1-7烷基，RP1选自C1-7烷基和C5-7芳基，RSi1和RSi2分别选自H、C1-7烷基、苄基和C5-7芳基，RB1选自C1-7烷基、C5-7芳基、C1-7烷氧基、C5-7芳氧基，RC1和RC2分别选自H、C1-7烷基和C1-7烷酯基；如果X为(CRC1RC2)2，则两个碳原子可以构成具有3至7个环原子的融合环烷或杂环；R1选自H、羟基、C1-7烷基、C1-7烷氧基、硅烷氧基、C1-7烷酯基；R2选自H、羟基、C1-7烷基、C1-7烷氧基、硅烷氧基、C1-7烷酯基；RP选自C5-20芳基、二(C1-7烷基)氨基、C1-7烷氧基、氯和C1-7烷基。
• (Z)-1-methoxy-4-(diphenylphosphino) but-1-ene-3-yne: A versatile synthon for unsymmetrically substituted (diphenylphosphino) diacetylene derivatives
  作者：Robert J.P. Corriu、Christian Guérin、Bernard J.L. Henner、Agnès Jolivet

  DOI：10.1016/s0022-328x(96)06655-7

  日期：1997.3

  An efficient synthesis of Ph2P-C equivalent to C-C equivalent to C-Li, 1, was found, starting from commercially available (Z)-1-methoxybut-1-ene-3-yne and its diphenylphosphino derivative 2. The lithio compound 1 was condensed with electrophiles to give Ph2P-C equivalent to C-C equivalent to C-Sigma (Sigma = SiR3, SnR3, B((NPr)-Pr-i)(2)) 3. Compound 2 was easily transformed into the phosphonium salt 6 and the phosphine oxide 7 using Mel and H2O2 respectively. Derivatives 3 (Z = SiMe3, SnMe3) are reactive at phosphorus and at the Sigma group; complexation with W(CO)(5)THF gave the expected derivatives W(CO)(5)Ph2P-C equivalent to C-C equivalent to C-Sigma (Sigma = SiMe3, SnMe3), 10, and in the case of Sigma = SnMe3, coupling reaction between Ph2P-C equivalent to-C-C equivalent to C-SnMe3, 3c, and (eta(5)-IC5H4)Mn(CO)(3) in the presence of PdCl2(CH3CN)(2) as a catalyst gave the complex 11, Ph2P-C equivalent to C-C equivalent to C-(eta(5)-C5H4)Mn(CO)(3).
• Synthesis and crystal structure of 9,10-dihydro-9,10-etheno-1,8-dichloro-11-diphenylphosphinyl-12-(diphenylphosphinylethynyl)anthracene
  作者：Yao Dong Huang、Hai Tao Yu、Ji Ben Meng、Teruo Matsuura、Yong Mei Wang

  DOI：10.1016/s0022-2860(02)00035-2

  日期：2002.6

  The title compound, 9,10-dihydro-9,10-etheno-1,8-dichloro-11-diphenylphosphinyl-12-(diphenylphosphinylethynyl)anthracene (1), has been synthesized and its crystal structure has been determined. The compound 1 crystallized into the triclinic space group P-1 with a = 11.881(3) Angstrom, b = 13.769(3) Angstrom, c = 14.034(3) Angstrom, alpha = 74.837(4)degrees, beta = 88.156(4)degrees, gamma = 65.398(4)degrees, V = 2007.1(7) Angstrom(3), Z = 2, D-c = 1.352 g cm(-3). In the crystal structure of la, one chloroform molecule was included by the compound 1 with a 1:1 ratio and the existence of non-classical intermolecular C-H...O hydrogen bonds, intramolecular C-H... Cl and C-H...O hydrogen bonds and pi-pi stacking were observed. (C) 2002 Elsevier Science B.V. All rights reserved.
• The crystal structure of a novel host 9,9′,10,10′-tetrahydro-9,10,9′,10′-biethenobianthracene -11,11′-bis-(diphenylphosphine oxide)-12,12′-diyl
  作者：Yao Dong Huang、Ji Ben Meng、Hai Tao Yu、Teruo Matsuura、Yong Mei Wang

  DOI：10.1016/s0022-2860(01)00654-8

  日期：2002.2

  The structure of a novel host 9,9',10,10'-tetrahydro-9,10,9',10'-biethenobianthracene-11,11'-bis-(diphenylphosphine oxide)12,12'-diyl, named TBB briefly, has been determined by X-ray diffraction. The framework of TBB is highly twisted because of its bulky substituents. Two chloroform and three water molecules are included in each TBB molecule. (C) 2002 Elsevier Science B.V. All rights reserved.
• Rhodium-Catalyzed Double [2 + 2 + 2] Cycloaddition of 1,4-Bis(diphenylphosphinoyl)buta-1,3-diyne with Tethered Diynes:  A Modular, Highly Versatile Single-Pot Synthesis of NU-BIPHEP Biaryl Diphosphines
  作者：Simon Doherty、Julian G. Knight、Catherine H. Smyth、Ross W. Harrington、William Clegg

  DOI：10.1021/ol702390p

  日期：2007.11.1

  procedure for the synthesis of a new class of tropos biaryl diphosphine, NU-BIPHEP. This methodology represents a significant improvement on existing multistep procedures. Enantiopure Lewis acid platinum complexes of these diphosphines are highly efficient catalysts for carbonyl-ene and Diels-Alder reactions, and ruthenium diphosphine-diamine complexes catalyze the asymmetric reduction of ketones to give

  铑催化的1,4-双（二苯基膦酰基）丁1,3-二炔与束缚二炔的双[2 + 2 + 2]环加成反应为合成新型对位联芳基二膦提供了一种简单的单釜法，NU-BIPHEP。这种方法代表了对现有多步骤程序的重大改进。这些二膦的对映纯路易斯酸铂络合物是羰基-烯和Diels-Alder反应的高效催化剂，钌二膦二胺络合物催化酮的不对称还原，得到的ee可以与用BINAP对应的ee竞争。