3-(diisopropylphosphino)indene | 628323-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 3-(diisopropylphosphino)indene
• 英文别名: 3-P-i-Pr2-indene；3H-inden-1-yl-di(propan-2-yl)phosphane
• CAS: 628323-99-9
• 化学式: C₁₅H₂₁P
• 分子量: 232.305
• InChiKey: APKMDULSKFYOEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  330.3±40.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-(diisopropylphosphino)indene 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [(κ1-P-C9H7P(i-Pr)2)2Au][OTf]
  参考文献：
  名称：

  Au(I) Complexes Supported by Donor-Functionalized Indene Ligands:  Synthesis, Characterization, and Catalytic Behavior in Aldehyde Hydrosilylation

  摘要：

  New Au(I) complexes featuring ligands of the type kappa(1)-3-R2P-indene (kappa(1)-1a, R = Pr-i; kappa(1)-1b, R = Ph) and kappa(1)-1-R2P-2-Me2N-indene (kappa(1)-1c, R = Pr-i; kappa(1)-1d, R = Ph) were prepared and structurally characterized. Dicoordinate neutral complexes (kappa(1)-1)AuCl (2-5) were prepared by reacting 1 with Me2SAuCl, with isolated yields ranging from 56 to 88%. Addition of a second equivalent of 1a to 2 resulted in formation of the tricoordinate neutral species (kappa(1)-1a)(2)AuCl (6; 69%). By treating 6 with AgOTf, the corresponding cationic complex [(kappa(1)-1a)(2)Au]+OTf- ([7]+OTf-; 72%) was obtained. The catalytic performance of these new Au(I) compounds in the hydrosilylation of various aldehydes was compared to that of catalyst systems derived from a combination of R3P (R = Et, Bu-n, Bu-t, Cy, or Ph) or N-heterocyclic carbene ligands and Me2SAuCl. While for the phosphine-substituted indene complexes, a catalyst mixture of 3 mol % 2 and 20 mol % 1a was found to be optimal, a catalyst derived from 3 mol % Me2SAuCl and 20 mol % Et3P, (Bu3P)-Bu-n, or (Bu3P)-Bu-t proved to be the most effective overall, especially for reactions conducted at 24 degrees C. Single-crystal X-ray diffraction data are provided for 2, 4, 6, and [7]+OTf-.

  DOI：

  10.1021/om060948n
• 作为产物：
  描述：

  氯二异丙基膦 、 茚 在 正丁基锂 作用下， 以 乙醚 为溶剂， 以94%的产率得到3-(diisopropylphosphino)indene
  参考文献：
  名称：

  合成，结构和外消旋/内消旋bisplanar手性双异构化行为（膦-η 5 -茚基）合铁（II）络合物

  摘要：

  膦基茚1-（二苯基膦基）-3-甲基茚（1b），3-（二苯基膦基）-2-甲基茚（1c），1-（二苯基膦基）-2,3-二甲基茚（1d），4,7-二甲基的合成通过用适当的氯膦处理适当的茚化物来进行-3-（二苯基膦基）茚（1e），1-（二苯基膦基）-3,4,7-三甲基茚（1f）和3-（二异丙基膦基）茚（1i）。 。通过用三甲基氯硅烷处理3-（二苯基膦基）茚基（1a）的茚化物来制备甲硅烷基膦基茚3-（二苯基膦基）-1-（三甲基甲硅烷基）茚基（1h）。除了1a以外，这些还表示然后，在用BuLi进行质子化后，用，，通过以2：1的比例的氯化亚铁处理，制备相应的茚基二茂铁2a - 2e，2h和2i。这些化合物通过1 H，13 C和31 P NMR光谱以及质谱进行表征，除了高度敏感的二异丙基膦2i只能通过31 P NMR光谱表征。所有这些二茂铁配合物都是双平面手性体系，可潜在形成外消旋和内消旋异构体。在所有情

  DOI：

  10.1016/j.jorganchem.2004.03.014

文献信息

• Divergent Isomerization Behavior and Rhodium(I) Coordination Chemistry of Indenyl Ligands Bearing either One or Two Pnictogen Donor Fragments
  作者：Judy Cipot、Dominik Wechsler、Mark Stradiotto、Robert McDonald、Michael J. Ferguson

  DOI：10.1021/om0340589

  日期：2003.12.1

  1-(Diphenylphosphino)-2-(dimethylamino)indene (2c) has been prepared in 61% yield and upon exposure to Al2O3 is mostly isomerized to 3-(diphenylphosphino)-2-(dimethylamino)indene (2d) (2c:2d ≈ 1:3); similarly, 1-(diisopropylphosphino)-2-(dimethylamino)indene (2a) is only partially converted to the corresponding C3 isomer (2b) upon treatment with Al2O3 (2a:2b ≈ 3:1). In contrast, 1-(diisopropylphosphino)indene

  1-（二苯基膦基）-2-（二甲基氨基）茚（2c）的制备产率为61％，暴露于Al 2 O 3时大部分被异构化为3-（二苯基膦基）-2-（二甲基氨基）茚（2d）（2c：2d≈1：3）; 类似地，1-（二异丙基）-2-（二甲基氨基）茚（2A）仅部分地转化成相应的C3异构体（2B）处理后用Al 2 ö 3（图2a：2B ≈3:1）。相反，已经以92％的收率制备了1-（二异丙基膦基）茚（6a），并且很容易将其转化为3-（二异丙基膦基）茚（6a）。6b）越过Al 2 O 3 ; 0.5当量的[（η 4 -COD）的RhCl] 2和图6B相结合，得到[（κ 1 - P -图6b）（η 4 -COD）的RhCl]（7），79％收率。或者2-（二甲氨基）茚（处理1）或图6b与化学计量量Ñ正丁基锂，然后加入0.5当量[（η的4 -COD）的RhCl] 2，产生了（η 5 -茚基）铑（I）配合物8（53％产率）
• New Racemic Planar-Chiral Metalloligands Derived from Donor-Substituted Indenes:  A Synthetic, Structural, and Catalytic Investigation
  作者：Dominik Wechsler、Matthew A. Rankin、Robert McDonald、Michael J. Ferguson、Gabriele Schatte、Mark Stradiotto

  DOI：10.1021/om700832f

  日期：2007.12.1

  The synthesis and characterization of a new family of (eta(5)-indenyl)MLn complexes (MLn = Mn(CO)(3), Cp*Ru, or Cp*Fe; Cp* = eta(5)-C5Me5) derived from 3-(PPr2)-Pr-i-indene, 1-(PPr2)-Pr-i-2-NMe2-indene (1a[H]), or 1-P(S)Pr-i(2)-2-NMe2-indene (1b[H]) are described. Lithiation of 1b[H] followed by treatment with BrMn(CO)(5), 0.25 equiv of [Cp*RuCl](4), or Cp*Li/FeCl2 provided the corresponding (eta(5)-1b)MLn complexes (MLn = Mn(CO)(3), 2a, 96%; Cp*Ru, 2b, 87%; or Cp*Fe, 2c, 55%). Similarly, treatment of 1a[Li] with 0.25 equiv of [Cp*RuCl](4) or Cp*Li/FeCl2 provided the corresponding (eta(5)-1a)MLn complexes (MLn = Cp*Ru, 3b, 74%; or Cp*Fe, 3c, 62%). Whereas combination of 3b and 0.5 equiv of [(COD)RhCl](2) afforded [(COD)Rh(kappa(2) -P,N-3b)]Cl-+(-) ([4b]Cl-+(-); 49% isolated yield), under similar conditions 3c was observed to undergo a decomposition reaction resulting in the formation of the zwitterionic complex (COD)Rh(kappa(2) -P,N-1a) (5; COD = eta(4)- 1, 5-cyclooctadiene). Each of 3a-c was observed to react cleanly with [(COD)Rh(THF)(2)]+BF4- (prepared in situ) to give the corresponding [(COD)Rh(kappa(2)-P,N-3a-c)]+BF4- complex ([4a-c]+BF4-; 87%, 96%, and 89% isolated yield, respectively). Whereas lithiation of 3-(PPr2)-Pr-i-indene followed by the addition of BrMn(CO)5 generated a complex mixture of products, similar reactions employing 0.25 equiv of [Cp*RuCl](4) Or Cp*Li/FeCl2 afforded 6b or 6c in 98% and 43% yield, respectively. Treatment of 6b with 0.5 equiv of [(COD)RhCl](2) allowed for the isolation of (COD)RhCl(kappa(1)-P-6b) 7 in 96% isolated yield. Each of [4a-c]+BF4- proved to be an active catalyst for addition of pinacolborane to styrene, with the observed regioselectivity being dependent on the nature of the eta(5)-coordinated metal fragment, as well as the solvent employed. Single-crystal X-ray diffraction data for 2a, 2b, 2c, 3b, [4c]+BF4-, and 7 are provided.