4,6,6-三甲基环己-1,3-二烯羧酸 | 103441-05-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 4,6,6-三甲基环己-1,3-二烯羧酸
• 英文名称: 4,6,6-Trimethylcyclohexa-1,3-dienecarboxylic acid
• 英文别名: 4,6,6-trimethyl-cyclohexa-1,3-dienecarboxylic acid；4,6,6-Trimethyl-cyclohexa-1,3-diencarbonsaeure；4,6,6-Trimethyl-1,3-cyclohexadiene-1-carboxylic acid；4,6,6-trimethylcyclohexa-1,3-diene-1-carboxylic acid
• CAS: 103441-05-0
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: JMRZNNKUYHPWKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,6,6-三甲基环己-1,3-二烯羧酸 在 草酰氯 作用下， 以 苯 为溶剂， 反应 2.0h， 以80%的产率得到4,6,6-三甲基-1,3-环己二烯-1-甲酰氯
  参考文献：
  名称：

  Synthesis of inverto-yuehchukene and its 10-(indol-3′-yl) isomer. X-Ray structure of (4aRS,10aRS)-1,1,3-trimethyl-1,2,4a,5,10,10a-hexahydroindene [1,2-b]indol-10-one

  摘要：

  A total synthesis of inverto-yuehchukene 4 and its 10-(indo-3'-yl) isomer 7 is described. The key tetracyclic ketone intermediate 13 was synthesized by a coupling reaction between 3-indolylzinc reagent and acid chloride 11, followed by Nazarov cyclization of the divinyl ketone 12. The indol-2-yl moiety present in inverto-yuehchukene 4 was introduced by palladium(0)-catalysed cross-coupling between indol-2-ylzinc reagent and the acetate 16.

  DOI：

  10.1039/p19960001213
• 作为产物：
  描述：

  Methyl 4,6,6-trimethylcyclohexa-1,3-dienecarboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以88%的产率得到4,6,6-三甲基环己-1,3-二烯羧酸
  参考文献：
  名称：

  Synthesis of inverto-yuehchukene and its 10-(indol-3′-yl) isomer. X-Ray structure of (4aRS,10aRS)-1,1,3-trimethyl-1,2,4a,5,10,10a-hexahydroindene [1,2-b]indol-10-one

  摘要：

  A total synthesis of inverto-yuehchukene 4 and its 10-(indo-3'-yl) isomer 7 is described. The key tetracyclic ketone intermediate 13 was synthesized by a coupling reaction between 3-indolylzinc reagent and acid chloride 11, followed by Nazarov cyclization of the divinyl ketone 12. The indol-2-yl moiety present in inverto-yuehchukene 4 was introduced by palladium(0)-catalysed cross-coupling between indol-2-ylzinc reagent and the acetate 16.

  DOI：

  10.1039/p19960001213

文献信息

• 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。
• Alkonyi; Szabo, Acta Chimica Academiae Scientiarum Hungaricae, 1957, vol. 12, p. 289,291,292
  作者：Alkonyi、Szabo

  DOI：——

  日期：——
• Kutney, James Peter; Lopez, Francisco Javier; Huang, Shyl-Pyng, Heterocycles, 1989, vol. 28, # 2, p. 565 - 572
  作者：Kutney, James Peter、Lopez, Francisco Javier、Huang, Shyl-Pyng、Kurobe, Hiroshi

  DOI：——

  日期：——
• PERFUMING INGREDIENTS WITH SAFFRON ODOR
  申请人：FIRMENICH SA

  公开号：EP1791934B1

  公开（公告）日：2010-07-07
• US8222199B2
  申请人：——

  公开号：US8222199B2

  公开（公告）日：2012-07-17