(E)-2,2-二甲基-4-己烯醛 | 920-08-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (E)-2,2-二甲基-4-己烯醛
• 中文别名: (2-氰乙基)三乙氧基硅烷；4-己烯醛,2,2二甲基-,(E)-
• 英文名称: (E)-2,2-dimethylhex-4-enal
• 英文别名: 2,2-dimethyl-hex-4t-enal；(4E)-2,2-dimethyl-4-hexenal
• CAS: 920-08-1
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: RTIRHTGJIQLEQV-SNAWJCMRSA-N

物化性质

• 沸点：
  162℃
• 密度：
  0.832
• 闪点：
  42℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2,2-二甲基-4-己烯醛 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 生成 2,2-二甲基-1-己醇
  参考文献：
  名称：

  EPR光谱对无环伯烷基的构象分析和立体动力学

  摘要：

  DOI：

  10.1021/j100404a017
• 作为产物：
  描述：

  2-丁烯基溴 、 N,N-dicyclohexyl-2-methyl-1-propen-1-ylamine 生成 (E)-2,2-二甲基-4-己烯醛
  参考文献：
  名称：

  Opitz,G., Justus Liebigs Annalen der Chemie, 1961, vol. 650, p. 122 - 132

  摘要：

  DOI：

文献信息

• Synthesis, conformation, and immunosuppressive activities of three analogs of cyclosporin A modified in the 1-position
  作者：Johannes D. Aebi、Donald T. Deyo、Chong Qing Sun、Dominique Guillaume、Brian Dunlap、Daniel H. Rich

  DOI：10.1021/jm00165a018

  日期：1990.3

  The syntheses of three new cyclosporin A (CsA) analogues that contain novel MeBmt derivatives in the 1-position are described. The MeBmt analogue that contains an additional methyl group on C4, (2S,3R,6E)-4,4-dimethyl-3-hydroxy-2-(N-methylamino)-6-octenoic acid (MeBm2t), was synthesized in four steps beginning with the reaction of Pmz-Sar-OtBu with (4E)-2,2-dimethyl-4-hexenal. The C4 desmethyl analogue

  描述了三个新的环孢菌素A（CsA）类似物的合成，这些类似物在1位上包含新颖的MeBmt衍生物。在四个分子中合成了在C4上包含一个额外甲基的MeBmt类似物（2S，3R，6E）-4,4-二甲基-3-羟基-2-（N-甲基氨基）-6-辛烯酸（MeBm2t）步骤开始于Pmz-Sar-OtBu与（4E）-2,2-二甲基-4-己烯醛的反应。MeBmt的C4脱甲基类似物（2S，3R，6E）-3-羟基-2-（N-甲基氨基）-6-辛烯酸（MeBth）通过Sharpless手性环氧化程序通过九步合成。MeBmt的炔基衍生物（2S，3R，4R）-4-甲基-3-羟基-2-（N-甲基氨基）-6-辛酸（MeByt）是通过修改Tung等人的方法合成的等 用于合成MeBmt。每个MeBmt类似物都被保护为N，O-丙酮化物并与六肽Abu-Sar-MeLeu-Val-MeLeu-Ala-OBzl偶联。将所得的七肽脱保护并与F
• Iodide-Catalysed Cyclization of Unsaturated N-Chloroamines: A New Way to Synthesise 3-Chloropiperidines
  作者：Michael Noack、Richard Göttlich

  DOI：10.1002/1099-0690(200209)2002:18<3171::aid-ejoc3171>3.0.co;2-l

  日期：2002.9
• Diastereoselective cycloisomerizations of enediynes via palladium catalysis
  作者：Barry M. Trost、Yian Shi

  DOI：10.1021/ja00079a033

  日期：1993.12

  Considerations of atom economy drive a search for reactions that are simple additions which, performed intramolecularly, are cycloisomerizations. Exposure of acyclic enediynes to a catalyst generated by mixing a Pd(O) complex with acetic acid normally in the presence of a phosphine ligand creates [5.6.51 and [6.6.51 tricycles with extraordinary diastereoselectivity of remote stereogenic centers. Effects of substituents on the tethers as well as the olefinic and acetylenic bonds reveal a wide tolerance of functionality. While geminal substitution facilitates the cycloisomerization, it is not required. Allylic oxygen plays a role as a regioselectivity control element. Cycloisomerization dominates over allylic ionization in such cases by proper tuning of the ligand. The mechanism of this reaction appears to vary depending upon the structure of the substrate. In the normal cases, the process involves three stages, initiation, propagation, and termination. Chemoselective initiation at the acetylenic linkage closest to one of the chain's termini occurs by hydropalladation. Propagation entails intramolecular carbametalations. Termination by beta-hydrogen elimination generates a hexatriene that undergoes high rotoselectivity in its disrotatory cyclization to generate the final product. Blocking formation of the hexatriene shuts down reaction. With substrates bearing a gamma-siloxypropiolate as the acetylenic initiator, cycloisomerization forms a tricycle with different positions of the double bonds. In contrast' to the case of the other substrates, blocking formation of a hexatriene does not shut down cycloisomerization. Invoking a novel intramolecular Diels-Alder reaction of a dienylpalladium intermediate derived from the diyne moiety with the olefin, likely assisted by coordination to palladium, accounts for our observations. The ease of availability of the acyclic substrates because of the versatility of the acetylenes combined with the high chemo-, regio-, and diastereoselectivity makes this atom-economical reaction a very practical approach for the construction of polycycles.
• Cresson,P., Bulletin de la Societe Chimique de France, 1964, p. 2618 - 2628
  作者：Cresson,P.

  DOI：——

  日期：——
• AEBI, JOHANNES D.;DEYO, DONALD T.;SUN, CHONG QING;GUILLAUME, DOMINIQUE;DU+, J. MED. CHEM., 33,(1990) N, C. 999-1009
  作者：AEBI, JOHANNES D.、DEYO, DONALD T.、SUN, CHONG QING、GUILLAUME, DOMINIQUE、DU+

  DOI：——

  日期：——