(3R,4R)-3,4-Bis(diphenylphosphino)pyrrolidin | 99135-90-7

• 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: (3R,4R)-3,4-Bis(diphenylphosphino)pyrrolidin
• 英文别名: (3R,4R)-(+)-Bis(diphenylphosphino)pyrrolidine；[(3R,4R)-4-diphenylphosphanylpyrrolidin-3-yl]-diphenylphosphane
• CAS: 99135-90-7
• 化学式: C₂₈H₂₇NP₂
• 分子量: 439.477
• InChiKey: YMRKZKDKJJCIHH-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3,4-Bis(diphenylphosphino)pyrrolidin 生成 (3R,4R)-1-Benzoyl-3,4-bis(diphenylphosphino)pyrrolidin
  参考文献：
  名称：

  BECK, W.;NAGEL, U.

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-bis(diphenylphosphoryl)-pyrrolidine 在 苯硅烷 作用下， 以 neat (no solvent) 为溶剂， 以73%的产率得到(3R,4R)-3,4-Bis(diphenylphosphino)pyrrolidin
  参考文献：
  名称：

  Pyrphos配体的新型高效合成

  摘要：

  [显示省略]

  DOI：

  10.1016/j.mencom.2024.01.015

文献信息

• The first stereospecific catalytic hydrogenation with a polymer supported optically active rhodium complex
  作者：U. Nagel、E. Kinzel

  DOI：10.1039/c39860001098

  日期：——

  Optical yields up to 100% are obtained in the heterogeneous hydrogenation of α-(acetylamino)cinnamic acid and its methyl ester in the presence of rhodium complexes of 3,4-(R,R)-bis(diphenylphosphino)pyrrolidine, bound covalently to silica.

  在3,4-（R，R）-双（二苯基膦基）吡咯烷铑配合物共价结合的铑配合物存在下，通过α-（乙酰氨基）肉桂酸及其甲酯的异质氢化可获得高达100％的光学收率。二氧化硅。
• Catalytic hydrogenation of itaconic acid in a biotinylated Pyrphos–rhodium(I) system in a protein cavity
  作者：Chi-Ching Lin、Ching-Wen Lin、Albert S.C. Chan

  DOI：10.1016/s0957-4166(99)00193-7

  日期：1999.5

  system embedded at a specific site in a protein has been studied. The preparation of the biotinylated Pyrphos–Rh(I) complex attached to the binding site in avidin and its application to the asymmetric hydrogenation of itaconic acid have been investigated. By introducing the chiral Pyrphos–Rh(I) moiety into the constrained environment of the protein cavity it was found that the enantioselectivity of the

  已经研究了嵌入蛋白质中特定位点的手性催化剂体系的构建。研究了生物素化的Pyrphos-Rh（I）复合物在亲和素结合位点的制备及其在衣康酸不对称氢化中的应用。通过将手性Pyrphos-Rh（I）部分引入蛋白质腔体的受限环境中，发现该系统的对映选择性受到抗生物素蛋白腔体中三级构象的显着影响。报道了反应条件如温度，氢气压力和缓冲液的pH值对映选择性的影响。
• Preparation and use of MeO-PEG-supported chiral diphosphine ligands: soluble polymer-supported catalysts for asymmetric hydrogenation
  作者：Qing-Hua Fan、Guo-Jun Deng、Chi-Ching Lin、Albert S.C Chan

  DOI：10.1016/s0957-4166(01)00210-5

  日期：2001.5

  Two new chiral MeO-PEG-supported (R)-BINAP and (3R,4R)-Pyrphos ligands were synthesized and employed in the Ru(II)- and Rh(I)-catalyzed asymmetric hydrogenation of 2-(6′-methoxy-2′-naphthyl)propenoic acid 5 and prochiral enamides 10. The results showed that these new soluble polymeric catalysts exhibited high catalytic activity and enantioselectivity. Enantiomeric excesses (e.e.s) in the ranges 90–96%

  合成了两个新的手性MeO-PEG负载的（R）-BINAP和（3 R，4 R）-Pyrphos配体，并将其用于Ru（II）和Rh（I）催化的2-（6'）不对称氢化中-甲氧基-2'-萘基）丙烯酸5和前手性酰胺10。结果表明，这些新型的可溶性聚合物催化剂表现出高的催化活性和对映选择性。在5和10的氢化中，分别达到90-96％和86-96％的对映体过量（ee）。此外，这些催化剂可以容易地回收，并且表明再循环的催化剂在随后的反应中保持了它们的效率。
• Simply Modified Chiral Diphosphine: Catalyst Recyclingvia Non-covalent Absorption on Carbon Nanotubes
  作者：Liang Xing、Jian-Hua Xie、Yong-Sheng Chen、Li-Xin Wang、Qi-Lin Zhou

  DOI：10.1002/adsc.200700617

  日期：2008.5.5

  A new type of recyclable chiral catalyst system was developed by absorption of pyrene-modified Pyrphos rhodium catalyst onto carbon nanotubes via π-π stacking interaction. This modified catalyst was successfully applied in the asymmetric hydrogenation of α-dehydroamino esters for nine cycles without obvious deterioration of activity and enantioselectivity.

  通过by修饰的Pyrphos铑催化剂通过π-π堆积相互作用吸附到碳纳米管上，开发了一种新型的可回收手性催化剂体系。该改性催化剂成功用于α-脱氢氨基酯的不对称加氢反应九个循环，活性和对映选择性均未明显下降。
• Molecular weight-enlarged ligands for asymmetric, homogeneously soluble hydrogenation catalysts, process for the production thereof and use
  申请人：Krimmer Hans-Peter

  公开号：US20050101813A1

  公开（公告）日：2005-05-12

  A molecular weight-enlarged, homogeneously soluble ligand, useful in catalysts, particularly for the synthesis of enantiomerically enriched organic compounds, includes: a weight average molecular weight of at least 1000 g/mol; a molecular weight-enlarging polymer; optionally, a polymer linker; and at least one homochiral active center; wherein the active center is bound to the molecular weight-enlarging polymer through the polymer linker or is bound directly to the molecular weight-enlarging polymer.

  一种分子量增大的、均匀可溶的配体，在催化剂中特别有用，特别用于合成对映富集的有机化合物，包括：至少1000克/摩尔的重均分子量；一种分子量增大的聚合物；可选地，一种聚合物连接物；以及至少一个同手性活性中心；其中活性中心通过聚合物连接物与分子量增大的聚合物结合，或直接与分子量增大的聚合物结合。