1,10-diiodo-5(Z)-decene | 244771-27-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 1,10-diiodo-5(Z)-decene
• CAS: 244771-27-5
• 化学式: C₁₀H₁₈I₂
• 分子量: 392.062
• InChiKey: HUQGXUJCOSYLFE-UPHRSURJSA-N

物化性质

• 沸点：
  334.2±35.0 °C(Predicted)
• 密度：
  1.743±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  12.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,10-diiodo-5(Z)-decene 、 alkaline earth salt of/the/ methylsulfuric acid 在 间氯过氧苯甲酸 作用下， 生成 (-)-disparlure
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1016006600263
• 作为产物：
  描述：

  2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran 在 Lidlar catalyst N-碘代丁二酰亚胺 、 正丁基锂 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 1,10-diiodo-5(Z)-decene
  参考文献：
  名称：

  Inhibition of Protein Kinase Cα by Dequalinium Analogues:  Dependence on Linker Length and Geometry

  摘要：

  Analogues of a bipartite compound, dequalinium (DECA) (quinolinium, 1,1'-(1,10-decanediyl)bis(4-amino-2-methyl diiodide)), were tested for inhibition of protein kinase C alpha (PKC alpha). In vitro assays of monomeric and dimeric analogues support a model in which DECA inhibits PKC alpha by an obligatory two-point contact, a unique mechanism among PKC inhibitors. The presence of unsaturation in the center of the C-10-alkyl linker produced geometric isomers with different inhibitory potencies: cis IC50 = 52 +/- 12 mu M and trans IC50 = 12 +/- 3 mu M, where the trans isomer was equipotent to that of the saturated C-10-DECA. DECA analogues with longer, saturated linkers (C-12, C-14, or C-16) exhibited enhanced inhibitory potencies which reached a plateau with the C-14-linker (IC50 = 2.6 +/- 0.2 mu M) Metastatic melanoma cells treated with 250 nM C-12-, C-14-, or C-16-DECA and irradiated with long-wave UV light (which causes irreversible inhibition of PKC alpha by DECA) confirmed the linker-dependent inhibition of intracellular PKC alpha activity.

  DOI：

  10.1021/jm990340z

文献信息

• Catalytic allylic oxidation of internal alkenes to a multifunctional chiral building block
  作者：Liela Bayeh、Phong Q. Le、Uttam K. Tambar

  DOI：10.1038/nature22805

  日期：2017.7

  enantioselective allylic carbon–hydrogen oxidation of alkenes has streamlined the production of pharmaceuticals, natural products, fine chemicals and other functional materials. Allylic functionalization provides a direct path to chiral building blocks with a newly formed stereocentre from petrochemical feedstocks while preserving the olefin functionality as a handle for further chemical elaboration. Various

  碳氢化合物的立体选择性氧化是过去五十年来合成化学领域最显着的进展之一。受自然界的启发，已经开发出不饱和烃的对映选择性二羟基化，环氧化和其他氧化。最近，烯烃的催化对映选择性烯丙基碳氢氧化简化了药物，天然产物，精细化学品和其他功能材料的生产。烯丙基官能化为从石油化学原料中新形成的立体中心提供了一条通向手性结构单元的直接途径，同时保留了烯烃官能度作为进一步化学精制的一种手段。已经发现了各种金属基催化剂，用于具有环或末端双键的简单烯烃的对映选择性烯丙基碳氢氧化。然而，使用更常见的内部烯烃进行的一般性和选择性烯丙基氧化仍然难以实现。在这里，我们报告了未活化的内部烯烃的催化对映选择性，区域选择性和E / Z选择性烯丙基氧化反应，该反应是通过与硫属元素基氧化剂的催化杂烯反应进行的。我们的方法可以使非对称内部烯烃选择性地转化为具有高立体选择性和区域选择性的烯丙基官能化产物。
• Synthesis of Z-isomeric insect sex pheromone components via ethenolysis of 1,5-cyclooctadiene
  作者：Victor I Bykov、Tamara A Butenko、Elena B Petrova、Eugene Sh Finkelshtein

  DOI：10.1016/s0040-4020(99)00295-1

  日期：1999.7

  A novel syntheses of Z-5-decenol, Z-5-decenyl acetate, Z-7-dodecenol, Z-7-dodecenyl acetate, Z-9-tricosene, Z-7,8-epoxy-2-methyloctadecane which are sex pheromone components of Lepidoptera and Diptera orders, have been realized via stereoselective cometathesis of 1,5-cyclooctadiene with ethylene in the presence of MoCl5/SiO2-SnMe4 as a key reaction. The main cometathesis product, 1,Z-5,9-decatriene, has been converted into pheromone components mentioned above by regioselective partial hydroboration or hydrozirconation with help of 9-BBN and Cp2ZrHCl, correspondingly. The protonolysis of the obtained zirconosene derivative gave 1,Z-5-decadiene. Hydroboration-oxidation or hydroboration-Cz-homologation of the latter led to Z-5- or Z-7 monoene pheromone components. Hydroboration-iodination of terminal double bond in 1,Z-5,9-decatriene, and further cross-coupling of the obtained iodine derivative with convenient lithium cuprates resulted in Z-9-tricosene, the main sex pheromone component of House Fly ( Musca Domestica), or in 2-methyl-Z-7-octadecene, the precursor of Gypsy Moth (Lymantria Dispar) sex attractant. (C) 1999 Elsevier Science Ltd. All rights reserved.