ethyl (E)-5-(2,6,6-trimethylcyclohexen-1-yl)pent-4-en-2-ynoate | 174836-75-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-5-(2,6,6-trimethylcyclohexen-1-yl)pent-4-en-2-ynoate
• CAS: 174836-75-0
• 化学式: C₁₆H₂₂O₂
• 分子量: 246.349
• InChiKey: PAXPREFWYJPUML-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (E)-5-(2,6,6-trimethylcyclohexen-1-yl)pent-4-en-2-ynoate 在 二异丁基氢化铝 作用下， 生成 4-(1,4-二甲基-1-乙基)戊基酚
  参考文献：
  名称：

  Stereoselective synthesis and receptor activity of conformationally defined retinoid X receptor selective ligands

  摘要：

  Retinoid X Receptor (RXR) specific ligands are currently being investigated for the treatment of metabolic diseases such as type II diabetes. We report the synthesis of conformationally locked retinoids, which are potent RXR selective ligands, and the attempted synthesis of 9-cyclopropyl locked analogs of RA and 9-cis RA. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00048-7
• 作为产物：
  描述：

  2,6,6-三甲基-1-环己烯基乙醛 在 四(三苯基膦)钯 copper(l) iodide 、 potassium tert-butylate 、 二异丙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 4.0h， 生成 ethyl (E)-5-(2,6,6-trimethylcyclohexen-1-yl)pent-4-en-2-ynoate
  参考文献：
  名称：

  烯醇九氟甲磺酸酯与（乙烯基）三丁基锡烷和乙炔的钯催化偶联反应

  摘要：

  通过钯催化烯醇壬酯与（乙烯基）三丁基锡烷和乙炔的交叉偶联反应，开发了一种立体选择性合成三烯和二炔的新方法，收率良好至极好。在这里，与相应的烯醇三氟甲磺酸酯相比，烯醇九氟甲磺酸酯在偶联反应中表现出更高的反应性。

  DOI：

  10.1055/s-2002-32602

文献信息

• Stereoselective Functionalization at C-9 of Retinal: Synthesis of 9-trans-19-Nor-9-haloretinal Analogs.
  作者：Tetsuro SHINADA、Kazuo YOSHIHARA

  DOI：10.1248/cpb.44.264

  日期：——

  Stereoselective functionalization at C-9 of retinal based on the use of the C4+X-unit is described. A sequential linkage of C4+X-units (X=Cl, Br, and I) with ylide 8 (C10) and phosphonate 12 (C5)selectively gave 9-trans-19-nor-9-Cl, Br, and I-retinal derivatives.

  基于C4+X单元的使用，报道了视黄醛C-9位点的立体选择性功能化。通过C4+X单元（X=Cl、Br和I）与亚砜8（C10）和膦酸盐12（C5）的序列连接，选择性地合成了9-反-19-去甲-9-氯、溴和碘-视黄醛衍生物。
• Palladium Catalyzed Coupling Reaction of an Enol Nonaflate with (Vinyl)tributylstannanes and Acetylenes
  作者：Akimori Wada、Yasuhiro Ieki、Masayoshi Ito

  DOI：10.1055/s-2002-32602

  日期：——

  stereoselective synthesis of trienes and dienynes was developed by palladium catalyzed cross coupling reactions of an enol nonaflate with (vinyl)tributylstannanes and acetylenes in good to excellent yields. Here, the enol nonaflate exhibited a higher reactivity compared with the corresponding enol triflate in the coupling reactions.

  通过钯催化烯醇壬酯与（乙烯基）三丁基锡烷和乙炔的交叉偶联反应，开发了一种立体选择性合成三烯和二炔的新方法，收率良好至极好。在这里，与相应的烯醇三氟甲磺酸酯相比，烯醇九氟甲磺酸酯在偶联反应中表现出更高的反应性。
• Palladium-Catalyzed Coupling Reaction of an Enol Nonaflate with (Vinyl)tributylstannanes and Acetylenes: A Highly Stereoselective Synthesis of 8,18-¹³C₂-Labeled Retinal
  作者：Akimori Wada、Yasuhiro Ieki、Saeko Nakamura、Masayoshi Ito

  DOI：10.1055/s-2005-865294

  日期：——

  Here we report that enol nonaflates exhibit higher reactivity than the corresponding enol triflates in palladium-catalyzed cross-coupling reactions with various (vinyl)tributylstannanes and acetylenes. We also highlight the reaction of a vinyl nonaflate, containing two 1 3 C-labeled carbon atoms with an alkenyl stannane, which afforded the trisubstituted E-olefin stereoselectively in high yield. The

  在这里，我们报告烯醇九氟甲磺酸酯在钯催化的与各种（乙烯基）三丁基锡烷和乙炔的交叉偶联反应中表现出比相应的烯醇三氟甲磺酸酯更高的反应性。我们还强调了含有两个 1 3 C 标记的碳原子的乙烯基九烷基锡与烯基锡烷的反应，它以高产率立体选择性地提供了三取代的 E-烯烃。然后将 E-烯烃转化为相应的全 E-视黄醛。
• Stereoselective synthesis and receptor activity of conformationally defined retinoid X receptor selective ligands
  作者：Vidyasagar Vuligonda、Michael E. Garst、Roshantha A.S. Chandraratna

  DOI：10.1016/s0960-894x(99)00048-7

  日期：1999.2

  Retinoid X Receptor (RXR) specific ligands are currently being investigated for the treatment of metabolic diseases such as type II diabetes. We report the synthesis of conformationally locked retinoids, which are potent RXR selective ligands, and the attempted synthesis of 9-cyclopropyl locked analogs of RA and 9-cis RA. (C) 1999 Elsevier Science Ltd. All rights reserved.