1-propoxyindan

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1-propoxyindan
• 英文别名: 1-propoxy-2,3-dihydro-1H-indene
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: OBYZOHIUICEHQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-propoxyindan 在 Rh/Al₂O₃ 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、5.0 MPa 条件下， 生成 (1R,3aR,7aR)-1-Propoxy-octahydro-indene 、 perhydro-1-propoxyindane
  参考文献：
  名称：

  Functional-Group-Directed Diastereoselective Hydrogenation of Aromatic Compounds. 2¹

  摘要：

  Diastereoselective liquid-phase hydrogenation of a series of monosubstituted indan substrates was studied on supported rhodium catalysts. Predominantly the cis-cis diastereomer, obtained by hydrogenation from the diastereoface opposite the substituent at the stereogenic center, and the cis-trans diastereomer, obtained by hydrogenation from the diastereoface on the same side as the substituent, were formed. The diastereoselectivity depends on the balance between steric repulsion and electronic attraction of the substituent with the surface of the catalyst. For alkoxy and carboxyl groups (acid, methyl ester, and amide), the steric repulsion dominated and the cis-cis diastereomer was obtained with moderately high selectivity. The diastereoselectivity obtained in the hydrogenation was influenced by the addition of bases to the reaction mixture. Addition of triethylamine caused a small increase in the selectivity to the cis-cis diastereomer in some substrates, whereas the addition of NaOH significantly increased the selectivity toward the cis-trans isomer in all substrates.

  DOI：

  10.1021/jo991604s
• 作为产物：
  描述：

  2,3-二氢-1H-茚-1-醇 、 1-碘代丙烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 1-propoxyindan
  参考文献：
  名称：

  Functional-Group-Directed Diastereoselective Hydrogenation of Aromatic Compounds. 2¹

  摘要：

  Diastereoselective liquid-phase hydrogenation of a series of monosubstituted indan substrates was studied on supported rhodium catalysts. Predominantly the cis-cis diastereomer, obtained by hydrogenation from the diastereoface opposite the substituent at the stereogenic center, and the cis-trans diastereomer, obtained by hydrogenation from the diastereoface on the same side as the substituent, were formed. The diastereoselectivity depends on the balance between steric repulsion and electronic attraction of the substituent with the surface of the catalyst. For alkoxy and carboxyl groups (acid, methyl ester, and amide), the steric repulsion dominated and the cis-cis diastereomer was obtained with moderately high selectivity. The diastereoselectivity obtained in the hydrogenation was influenced by the addition of bases to the reaction mixture. Addition of triethylamine caused a small increase in the selectivity to the cis-cis diastereomer in some substrates, whereas the addition of NaOH significantly increased the selectivity toward the cis-trans isomer in all substrates.

  DOI：

  10.1021/jo991604s

文献信息

• Gold(I), Gold(III), and Heterometallic Gold(I)–Silver(I) and Gold(I)–Copper(I) Complexes of a Pyridazine-Bridged NHC/Pyrazole Hybrid Ligand and Their Initial Application in Catalysis
  作者：Jan Wimberg、Steffen Meyer、Sebastian Dechert、Franc Meyer

  DOI：10.1021/om300335w

  日期：2012.7.23

  two-stranded helical structures; racemization of the P and M enantiomers is much more facile in the Ag(I) case 3 but has a barrier of around 65 kJ/mol in the Cu(I) case 6, which is rationalized on the basis of the different coordination chemistry preferences of these two metal ions. 3 may bind two further Ag(I) ions to the central pyridazine N, giving 5. Treatment of 1Br with Br2 leads to bromination at the

  哒嗪桥联的NHC /吡唑配体L（HL = 3- [3-（2,4,6-三甲基苯基）-3 H-咪唑-1-基] -6-（3,5-二甲基吡唑-1-基） （-哒嗪）提供了有机金属和经典的N供体隔室，可作为多种均金属和异金属金（I）卡宾配合物的多功能支架。络合物[LAuX]（1 Cl，X = Cl; 1 Br，X = Br），[L 2 Au]（PF 6）（2），[L 2 AuAg]（BF 4）（PF 6）（3）， [L 2 AuAg 3（MeCN）6 ]（BF 4）4（5），和[L 2 AuCu的]（OTF）0.75（PF 6）1.25（6）已经被用X射线晶体学。在所有情况下的Au（I）结合到NHC部位，同时所述附加的Ag（I）在3中或Cu（I）6被容纳在吡唑衍生的位点。两个3和6形成两个链螺旋结构; P和M对映异构体的消旋化在Ag（I）情况3下更容易实现，但在Cu（I）情况6下具有约65 kJ /