5-Cyclodecin-1-ol | 25533-77-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Cyclodecin-1-ol
• 英文别名: Cyclodecin-6-ol；Cyclodec-5-yn-1-ol
• CAS: 25533-77-1
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: ABLYJQVULQQLCF-UHFFFAOYSA-N

物化性质

• 沸点：
  75-78 °C(Press: 0.5 Torr)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Cyclodecin-1-ol 180.0~200.0 ℃ 、100.0 Pa 条件下， 以66%的产率得到11-Oxabicyclo<4.4.1>undec-1-en
  参考文献：
  名称：

  Transformation of Hydroxycycloalkanones to Oxabicycloalkenes

  摘要：

  Oxabicycloalkenes, which represent anti-Bredt enol ethers, can be generated by catalytic dehydration of the hemiacetals of hydroxycycloalkanones (Method I). Another option is provided by the transformation of hydroxycycloalkanones to the corresponding 1,2,3-selenadiazoles and their thermal fragmentation on Cu powder (Method II). The intermediate hydroxycycloalkynes show a transannular addition of the OH group to the triple bond. Altogether seven new oxabicycloalk-1-enes were obtained by this methods.

  DOI：

  10.3987/com-09-11728
• 作为产物：
  描述：

  环癸-5-炔酮 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 5-Cyclodecin-1-ol
  参考文献：
  名称：

  Hanack,M. et al., Chemische Berichte, 1972, vol. 105, p. 421 - 433

  摘要：

  DOI：

文献信息

• Synthesis and Properties of Donor-Acceptor-Substituted Metal-Capped Fourfold-Bridged Cyclobutadienophanes
  作者：Rolf Gleiter、Rolf Roers、Jörg Classen、Albrecht Jacobi、Gottfried Huttner、Thomas Oeser

  DOI：10.1021/om9907270

  日期：2000.1.1

  The synthesis of the superphanes 4-8 could be achieved from (1,2,11,12-eta(4))-tricyclo[10.8.0.0(2,11)]eicosa-1, 11-diene-6,17-diyne}(eta(5)-cyclopentadienyl (15) and its methoxycarbonyl congener 14 by heating with R-CpCo(CO)(2) (R = H, CH3, (CH3)(5)). X-ray investigations on the superphanes 3, 6, and 8 reveal distances between the two cyclobutadiene units between 2.922 Angstrom (3) and 2.941 Angstrom (6). Investigations by means of cyclic voltammetry show a decrease of the first oxidation potentials with increasing number of CH3 substituents at the cyclopentadienyl ligands. The comparison between the first oxidation potentials of 2-6, 4-7, and 5-8 gives evidence for a partial charge delocalization over both CpCoCb fragments of the superphanes.
• Stepwise Approach to Metal-Capped 4-Fold-Bridged Cyclobutadienophanes
  作者：Rolf Gleiter、Heinrich Langer、Volker Schehlmann、Bernhard Nuber

  DOI：10.1021/om00002a051

  日期：1995.2

  The three cyclic alkynes 5-cyclononynol (31), 5-cyclodecynol (15), and 6-cycloundecynol (16) are dimerized with CpCo(COD) to the tricyclic dialcohols 17, 24, and 32, respectively. Oxidation of the alcohols yields the diketones 18, 19, 25, and 33 which can be transformed to the tricyclic diynes 23, 29, 30, and 36 via the bis(selenadiazole)s. Reaction of 23 with CpCo(CO)(2), Cp*Co(CO)(2), and Fe(CO)(5) yields superphanes in which both complexed cyclobutadiene (Cb) units are connected with four trimethylene chains. The reaction of 29/30 with CpCo(CO)(2) affords two isomeric CpCo-stabilized fourfold-bridged bicyclo[4.2.0]octa-2,4,7-dienes 43 and 44 besides the expected superphane 42 in which the CpCo-capped Cb units are connected by two trimethylene and two tetramethylene chains. The key compounds, tricyclic diynes 23 and 36, superphane 40, and bicyclooctatriene 44, have been characterized using X-ray structural analysis. Crystal data: 23, C25H29Co, triclinic, space group C-i(1), P $($) over bar$$ 1 (No. 2), a = 9.003 Angstrom, b = 10.399 Angstrom, c = 11.874 Angstrom, alpha = 93.45 degrees, beta = 101.45 degrees, gamma = 108.77 degrees, V = 1022.34 Angstrom(3), Z = 2; 36, C23H25CO, rhombic, space group D-2(4), P2(1)2(1)2(1) (NO. 19), a = 9.555(9) Angstrom, b = 12.86(1) Angstrom, c = 15.551(9) V = 1910.9 Angstrom(3), Z = 4; 40, C28H29CoFeO3, monoclinic, space group C-s(4), Cc (No. 9), a = 18.92(1) Angstrom, b = 8.499(6) Angstrom, c = 19.37(1) Angstrom, beta = 130.16 degrees, V = 2380.41 Angstrom(3), Z = 4; 44, C27H33Co, triclinic, space group C-i(1), P $($) over bar$$ 1 (No. 2), a = 8.269(3) Angstrom, b = 9.082(2) Angstrom, c = 13.72.4 Angstrom, a = 84.87(2)degrees, beta = 88.77(3)degrees, gamma = 80.62(2)degrees, V = 1012.8 Angstrom(3), Z = 2.
• Detert, Heiner; Antony-Mayer, Christina; Meier, Herbert, Angewandte Chemie, 1992, vol. 104, # 6, p. 755 - 757
  作者：Detert, Heiner、Antony-Mayer, Christina、Meier, Herbert

  DOI：——

  日期：——
• Transformation of Hydroxycycloalkanones to Oxabicycloalkenes
  作者：Herbert Meier、Guido Krämer、Heiner Detert

  DOI：10.3987/com-09-11728

  日期：——

  Oxabicycloalkenes, which represent anti-Bredt enol ethers, can be generated by catalytic dehydration of the hemiacetals of hydroxycycloalkanones (Method I). Another option is provided by the transformation of hydroxycycloalkanones to the corresponding 1,2,3-selenadiazoles and their thermal fragmentation on Cu powder (Method II). The intermediate hydroxycycloalkynes show a transannular addition of the OH group to the triple bond. Altogether seven new oxabicycloalk-1-enes were obtained by this methods.
• Hanack,M. et al., Chemische Berichte, 1972, vol. 105, p. 421 - 433
  作者：Hanack,M. et al.

  DOI：——

  日期：——