Tetraisopropyl 2,2'-[(1S,2S)-cyclopentane-1,2-diyl]bis[(4R,5R)-1,3,2-dioxaphospholane-4,5-dicarboxylate] | 168556-99-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: Tetraisopropyl 2,2'-[(1S,2S)-cyclopentane-1,2-diyl]bis[(4R,5R)-1,3,2-dioxaphospholane-4,5-dicarboxylate]
• 英文别名: dipropan-2-yl (4R,5R)-2-[(1S,2S)-2-[(4R,5R)-4,5-bis(propan-2-yloxycarbonyl)-1,3,2-dioxaphospholan-2-yl]cyclopentyl]-1,3,2-dioxaphospholane-4,5-dicarboxylate
• CAS: 168556-99-8
• 化学式: C₂₅H₄₀O₁₂P₂
• 分子量: 594.533
• InChiKey: AWQQGIHCTBESIW-FLNLFJTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  142.12
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Tetraisopropyl 2,2'-[(1S,2S)-cyclopentane-1,2-diyl]bis[(4R,5R)-1,3,2-dioxaphospholane-4,5-dicarboxylate] 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,2S)-1,2-Bisphosphanylcyclopentane
  参考文献：
  名称：

  Eckert, Christine; Dahlenburg, Lutz; Wolski, Alexander, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1995, vol. 50, # 7, p. 1004 - 1008

  摘要：

  DOI：
• 作为产物：
  描述：

  L-(+)-酒石酸二异丙酯 、 trans-1,2-bis(dichlorophosphino)cyclopentane 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以23%的产率得到Tetraisopropyl 2,2'-[(1S,2S)-cyclopentane-1,2-diyl]bis[(4R,5R)-1,3,2-dioxaphospholane-4,5-dicarboxylate]
  参考文献：
  名称：

  Eckert, Christine; Dahlenburg, Lutz; Wolski, Alexander, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1995, vol. 50, # 7, p. 1004 - 1008

  摘要：

  DOI：

文献信息

• Enantioselective Catalysis; 130: Optically Active Expanded Ligands Based on the trans-1,2-Substituted Cyclopentane Skeleton
  作者：Henri Brunner

  DOI：10.1055/s-1999-3597

  日期：1999.10

  New expanded bisphosphane ligands with a chiral trans-1,2-substituted cyclopentane skeleton were prepared. Polyaldehydes were accessible by coupling optically active bisphosphane precursors with branched aryl bromides. Optically active expanded ligands were obtained by condensation of the aldehydes with chiral amines and amino alcohols. The optically active ligands were tested in several model reactions of enantioselective catalysis, including allylic alkylation, hydrogenation (adopted to the use of water), and hydrosilylation.

  新扩展的双膦配体具有手性反式-1,2-取代环戊烷结构被制备出来。通过将光学活性的双膦前体与支链芳基溴化物偶联，可以获得多醛。通过将醛与手性胺和氨基醇缩合，获得了光学活性扩展配体。光学活性配体在多个手性选择性催化的模型反应中进行了测试，包括烯丙基烷基化、氢化（适用于水的使用）和氢硅化。
• Chirale Bisphosphane VI. Chelatkomplexe von Platin(II) mit racemischen und optisch reinen trans-Cyclopentan-1,2-diyl-bis(phosphonigsäurediester)- und trans-Cyclopentan-1,2-diyl-bis(phosphonigsäurediamid)-Liganden: Synthesen, Strukturen und C–H-Aktivierungsreaktionen
  作者：L Dahlenburg

  DOI：10.1016/s0022-328x(98)00617-2

  日期：1998.8.14

  New bidentate ligands of the type C5H8(PX2)(2) [PX2 = P(OMe)(2) (2), P(OPh)(2) (3), P[OCH(Me)Et-(S)](2) (4), P[OC6H9(Me)Pr-i-(1R)](2) (5), P[OCH(CO2Pri)-(R)-](2) (6), P[N(CH2)(5)-cyclo](2) (7), P[N(CH2)(4)O-cyclo](2) (8)] were prepared from rac-C5H8(PCl2)(2) (1) and the corresponding alcohols, diols, and secondary amines. These reacted with [(1,5-C8H12)Pt(CH2CMe3)(2)] to give Pt(II) derivatives, [C5H8P(OR)(2)}(2)Pt(CH2CMe3)(2)] [P(OR)(2) = P(OMe)(2) (9), P(OPh)(2) (10), P[OCH(Me)Et-(S)](2) (11), P[OC6H9(Me)Pr-i-(1R)](2) (12), P[OCH(CO2Pri-(R)-](2) (13)] and [C5H8P(NR2)(2)}(2)Pt(CH2CMe3)(2) [P(NR2)(2) = P[N(CH2)(5)-cyclo](2) (14), P[N(CH2)(4)O-cyclo](2) (15)], respectively. Controlled acidolysis of 9, 10, 12, and 13 yielded the chloro neopentyls [C5H8P(OR)(2)}(2)Pt(Cl)CH2CMe3] [(P(OR)(2) = P(OMe)(2) (16), P(OPh)(2) (17), P[OC6H9(Me)Pr-i-(1R)](2) (18), P[OCH(CO2Pri)-(R)-](2) (19)]. Their P-N-bonded analogues [C5H8P(NR2)(2)}(2)Pt(Cl)CH2CMe3] [P(NR2)(2) = P[N(CH2)(5)-cyclo](2) (20), P[N(CH2)(4)O-cyclo], (21)] were obtained by substituting the diene ligand of [(1,5-C8H12)Pt(Cl)CH2CMe3] for bidentates 7 and 8. Treatment of 20 and 21 with Na[BH(OMe)(3)] in THF provided neopentyl hydrides, [C5H8P(NR2)(2)}(2)Pt(H)CH2CMe3] [P(NR2)(2) = P[N(CH2)(4)-cyclo](2) (23), P[N(CH2)(4)O-cyclo](2) (24)], which exhibited similar inertness toward reductive elimination at temperatures below 60 degrees C as did the previously investigated P-C-substituted derivative [C5H8P(C6H11-cyclo)(2)}(2)Pt(H)CH2CMe3]. The crystal structures of [(1S, 2S)-C5H8 P[OC6H9(Me)Pri-(1R)](2)}(2)Pt(CH2CMe3)(2)], (1S,2S)-12, [C5H8P[N(CH2)(4)O-cyclo](2)}(2)Pt(CH2CMe3)(2)], 15, [(1S,2S)-C5H8P[OC6H9(Me)Pr-i- (1R)](2)}(2)Pt(Cl)CH2CMe3], (1S,2S)-18, and also of [C5H8P(OPh)(2)}PtCl2], 22, were determined by X-ray diffraction.