(1Z,6Z)-环癸-1,6-二烯 | 1124-79-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: (1Z,6Z)-环癸-1,6-二烯
• 中文别名: 1,6-二烯环十烷
• 英文名称: 1Z,6Z-cyclodecadiene
• 英文别名: cis-1,6-cyclodecadiene；(Z,Z)-1,6-dicyclodecadiene；(Z,Z)-1,6-Cyclodecadiene；cyclodeca-1,6-diene；1,6-cyclodecadiene；cyclodeca-1c,6c-diene；(1Z,6Z)-cyclodeca-1,6-diene
• CAS: 1124-79-4
• 化学式: C₁₀H₁₆
• 分子量: 136.237
• InChiKey: GWCMUONZBWHLRN-REXUQAFDSA-N

物化性质

• 保留指数：
  1103;1108;1108

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902199090

反应信息

• 作为反应物：
  描述：

  (1Z,6Z)-环癸-1,6-二烯 在 copper(I) chloride 叔丁基过氧化氢 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 异辛烷 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 (1S*,7S*,8R*)-7,8-Epoxy-2-cyclodecenol
  参考文献：
  名称：

  Simple Designs for the Construction of Complex trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations

  摘要：

  A successful design for the construction of trans-fused medium-size cyclic ethers is described. The key features of the synthesis are as follows: (i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one- or two-directional synthetic operations which generate external oxocycles in single reaction steps. The general approach involves the intramolecular addition of a stable gamma-alkoxy-substituted allylstannane to an aldehyde carbonyl group, and the entire reaction is conducted in a one-pot process which includes the following: (i) vic-diol fragmentation from the bridged oxabicyclic precursor and (ii) Lewis acid-induced cyclization of the resulting aldehyde-allylic tin system. While the present strategy was mostly developed around racemic models, the potential for adoption of;enantioselective features is immediate. The versatility, scope, limitations, and potential applications of the present technology are discussed in detail.

  DOI：

  10.1021/jo00089a034
• 作为产物：
  描述：

  1,5-二烯环十烷 在 aluminum oxide 、 sodium 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以92%的产率得到(1Z,6Z)-环癸-1,6-二烯
  参考文献：
  名称：

  Simple Designs for the Construction of Complex trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations

  摘要：

  A successful design for the construction of trans-fused medium-size cyclic ethers is described. The key features of the synthesis are as follows: (i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one- or two-directional synthetic operations which generate external oxocycles in single reaction steps. The general approach involves the intramolecular addition of a stable gamma-alkoxy-substituted allylstannane to an aldehyde carbonyl group, and the entire reaction is conducted in a one-pot process which includes the following: (i) vic-diol fragmentation from the bridged oxabicyclic precursor and (ii) Lewis acid-induced cyclization of the resulting aldehyde-allylic tin system. While the present strategy was mostly developed around racemic models, the potential for adoption of;enantioselective features is immediate. The versatility, scope, limitations, and potential applications of the present technology are discussed in detail.

  DOI：

  10.1021/jo00089a034

文献信息

• Oxidation of unsaturated linear and cyclic hydrocarbons by molecular oxygen catalyzed by complexes of transition metals
  作者：G. A. Dzhemileva、V. N. Odinokov、U. M. Dzhemilev

  DOI：10.1007/bf00953862

  日期：1987.1
• Macro Rings. XIII. Synthesis and Properties of 1,7-Cyclododecadiyne and Related Compounds¹
  作者：Donald J. Cram、Norman L. Allinger

  DOI：10.1021/ja01592a051

  日期：1956.6
• Pericyclic Domino reactions with 3,6-Bis(trifluoromethyl)-1,2,4,5-tetrazine: A convenient entry into azo cage compounds
  作者：Thilo Klindert、Peter von Hagel、Luzian Baumann、Gunther Seitz

  DOI：10.1002/prac.199733901111

  日期：——

  3,6-Bis(trifluoromethyl)-1,2,4,5-tetrazine (1) characterized by a highly reactive, electron deficient diazadiene system reacted with several cyclic and acyclic bis-dienophiles to yield the cage compounds 11, 19a,b, 31a,b and 41 in a pericyclic homo-domino reaction in good yields. The first step of the domino reactions is an inverse electron demand intermolecular Diels-Alder addition followed by elimination of nitrogen to give 4,5-dihydropyridazines which then undergo a terminaI ring closure to yield the cage compounds. The solvent employed and the reaction temperature is of crucial importance. Whereas in nitromethane and at elevated temperatures the main products are the cage compounds, at lower temperature and in dichloromethane as solvent the initially formed 4,5-dihydropyridazines are frequently converted to 1,4-dihydropyridazines by a 1,3-H-shift. Treatment of the tetrazine 1 with cyclooctatriene 23 did not lead to a cage compound in any case; instead via valence tautomeric species octa-1,3,5,7-tetraene 23a and bicyclo[4.2.0]octa-2,4-diene 23b the twofold pyridazine-substituted butadienes 24 and 26 together with the tricyclic cyclobuta[f]phthalazine 25 were formed.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Ag: MVol.B5, 1.3.2.8, page 67 - 72
  作者：

  DOI：——

  日期：——
• Odinakov, V. N.; Ishmuratov, G. Yu.; Galeeva, R. I., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 1.1, p. 46 - 49
  作者：Odinakov, V. N.、Ishmuratov, G. Yu.、Galeeva, R. I.、Sokol'skaya, O. V.、Sagitdinova, Kh. F.、Tolstikov, G. A.

  DOI：——

  日期：——