1,3-dimethyl-cyclohex-3-enecarbaldehyde | 142457-17-8

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: 1,3-dimethyl-cyclohex-3-enecarbaldehyde
• 英文别名: 3-Cyclohexene-1-carboxaldehyde, 1,3-dimethyl-；1,3-dimethylcyclohex-3-ene-1-carbaldehyde
• CAS: 142457-17-8
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: GBKFYIUZPUUNCX-UHFFFAOYSA-N

物化性质

• 沸点：
  183.4±29.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-甲基丙烯醛 、 天然橡胶 在 samarium diiodide bis(tetrahydrofuran) 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 1,4-dimethyl-cyclohex-3-enecarbaldehyde 、 1,3-dimethyl-cyclohex-3-enecarbaldehyde
  参考文献：
  名称：

  Diiodosamarium，狄尔斯-阿尔德和杂狄尔斯-阿尔德反应的催化剂前体

  摘要：

  SmI 2对环戊二烯或异戊二烯与各种亲二烯体之间的Diels-Alder反应以及杂Diels-Alder反应具有催化活性。

  DOI：

  10.1016/s0040-4039(00)77166-8

文献信息

• Ionic liquids and their use
  申请人：——

  公开号：US20040054231A1

  公开（公告）日：2004-03-18

  Ionic compounds having a freezing point of no more than 50° C., formed by the reaction of at least one amine salt of the formula R 1 R 2 R 3 R 4 N + X − (I) with at least one hydrated salt, which is a chloride, nitrate, sulphate or acetate of Li, Mg, Ca, Cr, Mn, Fe, Co, Ni, Cu, Zn, Cd, Pb, Bi, La or Ce; wherein R 1 , R 2 and R 3 are each independently a C 1 to C 5 alkyl or a C 6 to C 10 cycloalkyl group, or wherein R 2 and R 3 taken together represent a C 4 to C 10 alkylene group, thereby forming with the N atom of formula (I) a 5 to 11 membered heterocyclic ring, and wherein R 4 is hydrogen, or phenyl, or C 1 to C 12 alkyl or cycloalkyl group, optionally substituted with at least one group selected from OH, Cl, Br, F, I, phenyl, NH 2 , CN, NO 2 , COOR 5 , CHO, COR 5 and OR 5 , wherein R 5 is a C 1 to C 10 alkyl or cycloalkyl group, and X − is an anion capable of being complexed by the said hydrated salt. The compounds are useful as solvents, electrolytes, and catalysts, and have particular application in solvents/electrolytes for metal plating and electropolishing processes, in particular in chromium plating.

  具有冰点不超过50°C的离子化合物，由至少一种胺盐（化学式为R1R2R3R4N+X−（I））与至少一种水合盐反应形成，所述水合盐是Li、Mg、Ca、Cr、Mn、Fe、Co、Ni、Cu、Zn、Cd、Pb、Bi、La或Ce的氯化物、硝酸盐、硫酸盐或醋酸盐；其中R1、R2和R3分别独立地是C1到C5烷基或C6到C10环烷基，或者R2和R3一起代表C4到C10烷基烯基，从而与化学式（I）中的N原子形成5到11个成员的杂环环，其中R4是氢、苯基、C1到C12烷基或环烷基，可选择地取代至少一个来自OH、Cl、Br、F、I、苯基、NH2、CN、NO2、COOR5、CHO、COR5和OR5的基团，其中R5是C1到C10烷基或环烷基，X−是能够被所述水合盐络合的阴离子。这些化合物可用作溶剂、电解质和催化剂，在金属镀覆和电化学抛光过程中具有特殊应用，特别是在铬镀中。
• La reaction de Diels–Alder catalysee par les sels de bismuth (III)
  作者：Bernard Garrigues、Adyl Oussaid

  DOI：10.1016/s0022-328x(99)00230-2

  日期：1999.8

  We have studied the Diels–Alder reaction from the dienes (1–3) and dienophiles (4–6), catalyzed by bismuth triflate and bismuth chloride. We compared these two catalysts with SnCl4, ZnI2, AlCl3 and Cu(BF4)2 respectively. With bismuth derivatives we noted no polymerisation, a better yield and a good selectivity in cycloadditions.

  我们研究了由三氟甲磺酸铋和氯化铋催化的二烯（1-3）和亲二烯体（4-6）的狄尔斯-阿尔德反应。我们将这两种催化剂分别与SnCl 4，ZnI 2，AlCl 3和Cu（BF 4）2进行了比较。对于铋衍生物，我们注意到没有聚合，在环加成反应中具有更好的产率和良好的选择性。
• Bismuth(III) Chloride or Triflate-Catalyzed Dienophilic Activity of α-Ethylenic Aldehydes and Ketones
  作者：Bernard Garrigues、Ferdinand Gonzaga、Hélène Robert、Jacques Dubac

  DOI：10.1021/jo970389h

  日期：1997.7.1
• Enantioselective catalysts based on the chiral fragment (η5-C5Me5)Ir(Prophos) for Diels–Alder reactions
  作者：Daniel Carmona、Fernando Viguri、Ainara Asenjo、Fernando J. Lahoz、Pilar García-Orduña、Luis A. Oro

  DOI：10.1016/j.molcata.2014.01.021

  日期：2014.4

  The aqua complex (S-Ir,R-C)-[(eta(5)-C5Me5)Ir(Prophos)(H2O)][SbF6](2) [Prophos = (R)-propane-1,2-diyl-bis(diphenylphosphane)] is an active precursor for the asymmetric Diels-Alder reaction of acyclic enals with cyclopentadiene, 2,3-dimethylbutadiene and isoprene. Enantioselectivities up to 78% ee are achieved. The intermediate Lewis acid-dienophile complex (S-Ir,R-C)-[(eta(5)-C5Me5)Ir(Prophos)(ethyl acrolein)][SbF6](2) has been isolated and completely characterized, including the X-ray crystal structure determination. Structural parameters indicate that the disposition of the coordinated dienophile is controlled by CH/pi attractive interactions established between a phenyl group of the Prophos ligand and the aldehyde proton of the coordinated enal. Proton NMR data indicate that these interactions are maintained in solution. From diffractometric and spectroscopic data, the origin of the enantioselectivity is discussed. (C) 2014 Elsevier B.V. All rights reserved.
• Macromolecular materials in heterogeneous catalysis: an aluminium silasesquioxane gel as active catalyst in Diels–Alder reactions of enones
  作者：Hendrikus C. L. Abbenhuis、Hendrikus W. G. van Herwijnen、Rutger A. van Santen

  DOI：10.1039/cc9960001941

  日期：——

  A highly active, genuinely heterogeneous catalyst for liquid-phase Diels-Alder reactions of enones results from the silanol centred modification of an incompletely condensed silasesquioxane with trimethylaluminium, the resulting catalytic material being a gel that contains aluminium(III) siloxy functions (Al-O-Si) which are incorporated in a well defined, three-dimensional SiO framework.