4,6,6-trimethyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester | 23068-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,6,6-trimethyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester
• 英文别名: 4,6,6-Trimethyl-2-oxo-cyclohex-3-encarbonsaeure-aethylester；Ethyl 4,6,6-trimethyl-2-oxocyclohex-3-ene-1-carboxylate
• CAS: 23068-97-5
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: WCPXMBJUQTVKGP-UHFFFAOYSA-N

物化性质

• 沸点：
  285.2±40.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,6,6-trimethyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 甲基碘化镁 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 ethyl (1R,4S)-4-(1H-indol-3-yl)-4,6,6-trimethylcyclohex-2-ene-1-carboxylate
  参考文献：
  名称：

  A versatile synthetic route to the anti-implantation agent, yuehchukene, and its analogues

  摘要：

  一项详细研究已完成，旨在开发一种通用的合成途径，以合成有趣的二聚天然产物月竹烯（1）及其对映体6a-epi-月竹烯（2）。由于与1相关的抗着床活性，因此提供一种合成策略不仅对1，而且对一系列月竹烯类似物是重要的，希望这些类似物能具有更好的化学稳定性和（或）更高的生物活性。本文所述的实验利用了易得且廉价的异戊酮（6），满足了这些要求。关键词：月竹烯合成，月竹烯类似物，抗着床活性。

  DOI：

  10.1139/v91-141
• 作为产物：
  描述：

  异佛尔酮 、 氰基甲酸乙酯 在 正丁基锂 、 二异丙胺 、 dimethyl-propylene-urea 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以72%的产率得到4,6,6-trimethyl-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester
  参考文献：
  名称：

  Syntheses and odor of “bulky group”-modified sandalwood odorants: isophorono-β-santalol analogues

  摘要：

  Three osmophoric points have been found to be necessary for the scent of sandalwood odorants. One of these points is the bulky group in a certain distance from the osmophoric hydroxyl group. Such a hydrophobic moiety is part of the trimethylcyclopentenyl derivatives, the so called campholenals, among them many are known to exert a strong and long lasting sandalwood odor. In continuation of our SAR-studies of sandalwood odorants four isophorone analogues of beta-santalol have been synthesized. The hydrophobic region of these new isophorone derivatives is now a trimethylcyclohexene nucleus, so to speak an extension of the cyclopentene part of the campholenals by one methylene group. This modification changes the sandalwood odor drastically to woody odor notes, reminiscent only to sandalwood odor. The environs of the crowded trimethylcyclohexene nucleus demonstrate the sensitivity of sandalwood odor on the shape of the hydrophobic, bulky part of beta-santalol analogues. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.03.016

文献信息

• A new synthetic route to (.+-.)-Strigol
  作者：Oliver D. Dailey

  DOI：10.1021/jo00386a016

  日期：1987.5
• Condensation of mesityl oxide with acetoacetic ester
  作者：Joseph D. Surmatis、A. Walser、Jozef Gibas、R. Thommen

  DOI：10.1021/jo00829a042

  日期：1970.4
• Mayuranathan, Journal of the Indian Institute of Science, 1933, vol. <A> 16, p. 123
  作者：Mayuranathan

  DOI：——

  日期：——
• Syntheses and odor of “bulky group”-modified sandalwood odorants: isophorono-β-santalol analogues
  作者：J. Höfinghoff、G. Buchbauer、W. Holzer、P. Wolschann

  DOI：10.1016/j.ejmech.2006.03.016

  日期：2006.8

  Three osmophoric points have been found to be necessary for the scent of sandalwood odorants. One of these points is the bulky group in a certain distance from the osmophoric hydroxyl group. Such a hydrophobic moiety is part of the trimethylcyclopentenyl derivatives, the so called campholenals, among them many are known to exert a strong and long lasting sandalwood odor. In continuation of our SAR-studies of sandalwood odorants four isophorone analogues of beta-santalol have been synthesized. The hydrophobic region of these new isophorone derivatives is now a trimethylcyclohexene nucleus, so to speak an extension of the cyclopentene part of the campholenals by one methylene group. This modification changes the sandalwood odor drastically to woody odor notes, reminiscent only to sandalwood odor. The environs of the crowded trimethylcyclohexene nucleus demonstrate the sensitivity of sandalwood odor on the shape of the hydrophobic, bulky part of beta-santalol analogues. (c) 2006 Elsevier SAS. All rights reserved.
• A versatile synthetic route to the anti-implantation agent, yuehchukene, and its analogues
  作者：James P. Kutney、Francisco J. Lopez、Shyh-Pyng Huang、Hiroshi Kurobe、Robert Flogaus、Krystyna Piotrowska、Steven J. Rettig

  DOI：10.1139/v91-141

  日期：1991.6.1

  A detailed study directed toward the development of a versatile synthetic route to the interesting dimeric natural product yuehchukene (1) and its epimer, 6a-epi-yuehchukene (2), has been completed. Due to the anti-implantation activity associated with 1, it was important to provide a synthetic strategy not only to 1, but to a family of yuehchukene analogues that, hopefully, would reveal superior chemical stability and (or) elevated biological activity. The experiments described herein and which utilize the readily available and inexpensive isophorone (6) satisfy these requirements. Key words: yuehchukene synthesis, yuehchukene analogues, anti-implantation activity.

  一项详细研究已完成，旨在开发一种通用的合成途径，以合成有趣的二聚天然产物月竹烯（1）及其对映体6a-epi-月竹烯（2）。由于与1相关的抗着床活性，因此提供一种合成策略不仅对1，而且对一系列月竹烯类似物是重要的，希望这些类似物能具有更好的化学稳定性和（或）更高的生物活性。本文所述的实验利用了易得且廉价的异戊酮（6），满足了这些要求。关键词：月竹烯合成，月竹烯类似物，抗着床活性。