Methyl 4,6,6-trimethylcyclohexa-1,3-dienecarboxylate | 179104-41-7

• 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
• 英文名称: Methyl 4,6,6-trimethylcyclohexa-1,3-dienecarboxylate
• 英文别名: Methyl 4,6,6-trimethylcyclohexa-1,3-diene-1-carboxylate
• CAS: 179104-41-7
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: PUXZPUGSJZUTIL-UHFFFAOYSA-N

物化性质

• 沸点：
  229.2±19.0 °C(Predicted)
• 密度：
  0.974±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  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
• 作为产物：
  描述：

  甲醇 、 4,6,6-trimethyl-1,3-cyclohexadiene-1-carboxaldehyde 在 manganese(IV) oxide 、 氰化钠 、 溶剂黄146 作用下， 反应 48.0h， 以64%的产率得到Methyl 4,6,6-trimethylcyclohexa-1,3-dienecarboxylate
  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

• 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
• [EN] PERFUMING INGREDIENTS WITH SAFFRON ODOR<br/>[FR] SUBSTANCES ODORANTES AU PARFUM DE SAFRAN
  申请人：FIRMENICH & CIE

  公开号：WO2006030268A1

  公开（公告）日：2006-03-23

  The present invention concerns the use as perfuming ingredient of a lower alkyl ester of 4,6,6-trimethyl-1,3-cyclohexadiene-1-carboxylate or 4,6,6-trimethyl-3-cyclohexene-1-carboxylate. Said compounds are able to impart odor notes of the spicy/saffron type.
• 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
  作者：Kin-Fai Cheng、Man-Ki Cheung

  DOI：10.1039/p19960001213

  日期：——

  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.