(4aR,8aS)-1,4,4a,5,8,8a-hexahydro-2,5,5,8a-tetramethylnaphthalen-1-one | 110188-67-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,8aS)-1,4,4a,5,8,8a-hexahydro-2,5,5,8a-tetramethylnaphthalen-1-one
• 英文别名: 11-nordrima-2,7-diene-9-one；(4aS,8aS)-2,5,5,8a-tetramethyl-4a,8-dihydro-4H-naphthalen-1-one
• CAS: 110188-67-5
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: DKKHCMAKACKEJZ-FZMZJTMJSA-N

物化性质

• 沸点：
  281.8±40.0 °C(Predicted)
• 密度：
  0.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  (4aR,8aS)-1,4,4a,5,8,8a-hexahydro-2,5,5,8a-tetramethylnaphthalen-1-one 、 11-nordrima-1,7-diene-9-one 以65%的产率得到
  参考文献：
  名称：

  GESSON, JEAN-PIERRE;JACQUESY, JEAN-CLAUDE;RENOUX, BRIGITTE, TETRAHEDRON, 45,(1989) N8, C. 5853-5866

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-Carvone 在 吡啶 、 sodium tetrahydroborate 、 三氯氧磷 作用下， 生成 (4aR,8aS)-1,4,4a,5,8,8a-hexahydro-2,5,5,8a-tetramethylnaphthalen-1-one
  参考文献：
  名称：

  香芹酮与手性反式和顺式稠合双环酮的新环化反应

  摘要：

  香芹酮在C 4的两个区域特异性连续烷基化，然后进行酸催化的环化反应，得到双环酮，这是合成几种萜烯的潜在中间体。取决于烷基化的顺序，可以仅在三个步骤中制备反式稠合酮或顺式稠合酮和顺式稠合酮的混合物，因此构成了香芹酮的新型环化反应。

  DOI：

  10.1016/s0040-4039(00)84979-5

文献信息

• A new annulation of carvone to chiral trans and cis fused bicyclic ketones
  作者：Jean-Pierre Gesson、Jean-Claude Jacquesy、Brigitte Renoux

  DOI：10.1016/s0040-4039(00)84979-5

  日期：1986.1

  Two regiospecific consecutive alkylations of carvone at C4 followed by acid-catalysed cyclisation afford bicyclic ketones which are potential intermediates for the synthesis of several classes of terpenes. Depending on the sequence of alkylation trans fused ketone or a mixture of and cis fused ketone may be prepared in only three steps, thus constituting a new type of annulation of carvone.

  香芹酮在C 4的两个区域特异性连续烷基化，然后进行酸催化的环化反应，得到双环酮，这是合成几种萜烯的潜在中间体。取决于烷基化的顺序，可以仅在三个步骤中制备反式稠合酮或顺式稠合酮和顺式稠合酮的混合物，因此构成了香芹酮的新型环化反应。
• A New Route to 2,7- and 7-Functionalized Labdanes
  作者：Ulrich Hersel、Melanie Steck、Karlheinz Seifert

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1609::aid-ejoc1609>3.0.co;2-2

  日期：2000.4
• Palladium-Mediated Ring Closure Reactions. Facile Syntheses of Enantiopure Bicyclic and Tricyclic Alkenones
  作者：Duy H Hua、Kiyosei Takasu、Xiaodong Huang、Gail S Millward、Yi Chen、Jingmei Fan

  DOI：10.1016/s0040-4020(00)00658-x

  日期：2000.9

  (R)-Carvone was used as a chiral building block. Regio- and stereoselective alkylations at C6 and C2 of (R)-carvone and (R)-5-isopropyl-2-methyl-2-cyclohexenone [derived from the hydrogenation of (R)-carvone] followed by palladium-mediated ring closures afforded various enantiopure bicyclic and tricyclic alkenones. Hence, cyclization of (5S,6S)-2,6-dimethyl-6-(cis-3-iodo-2-propenyl)-5-isopropenyl-2-cyclohexenone (3) gave (4aS,5S,8aS)-1,4,4a,5,8,8a-hexahydro-5-(methoxycarbonylmethyl)-2,5,8a-trimethylnapthalen-1-one (7) as the major product, cyclization of (5S,6S)-2,6-dimethyl-6-(cis-3-iodo-2-propenyl)-5-isopropyl-2-cyclohex (22) produced (1S,5R,6S)-1,5-dimethyl-6-isopropyltricyclo[3.3.1.0(2,8)]-3-nonen-9-one (23), and cyclization of (2R,5S,6S)-2,6-dimethyl-2-(cis-3-iodo-2-propenyl)-5-isopropenyl-3-cyclohexen- 1-one (25) afforded (3aR,6S,7aR)-6,7a-dimethyl-5-isopropenyl-3a,6,7,7a-tetrahydro-1H-inden-7-one (26). A 1,2-rearrangement reaction of bromide 16 gave hexahydro-1H-benzocycloheptene 17. (C) 2000 Elsevier Science Ltd. All rights reserved.
• GESSON, JEAN-PIERRE;JACQUESY, JEAN-CLAUDE;RENOUX, BRIGITTE, TETRAHEDRON, 45,(1989) N8, C. 5853-5866
  作者：GESSON, JEAN-PIERRE、JACQUESY, JEAN-CLAUDE、RENOUX, BRIGITTE

  DOI：——

  日期：——
• A new chiral route toward terpenoids. Annulation of carvone to trans- and cis-fused bicyclic synthons
  作者：Jean-Pierre Gesson、Jean-Claude Jacquesy、Brigitte Renoux

  DOI：10.1016/s0040-4020(01)89112-2

  日期：1989.1

  potentially useful chirons for synthesis of terpenes such as drimanes, labdanes and triterpenes. The stereoselectivity of the second alkylation step which determines the stereochemistry of the ring junction has been studied and the results explained by the model of Tomioka. Several types of products may be formed depending on the acid used and a rearrangement has been observed in one case.

  从香芹酮开始，在C-6处连续进行两次烷基化反应1，然后进行酸催化的环化反应，生成新的双环酮，这对于合成萜烯（如杜曼，拉丹和三萜烯）可能是有用的Chirons。已经研究了确定环结的立体化学的第二个烷基化步骤的立体选择性，并通过Tomioka模型解释了结果。取决于所使用的酸，可能形成几种类型的产物，并且在一种情况下已经观察到重排。