(4aR,5S)-4a,5-dimethyl-4,4a,5,6-tetrahydronaphthalen-2(3H)-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,5S)-4a,5-dimethyl-4,4a,5,6-tetrahydronaphthalen-2(3H)-one
• 英文别名: (4aR,5S)-4a,5-dimethyl-3,4,5,6-tetrahydronaphthalen-2-one
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: JJAXFFQAVKIBRO-JOYOIKCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 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,5S)-4a,5-dimethyl-4,4a,5,6-tetrahydronaphthalen-2(3H)-one 在 叔丁基过氧化氢 、 重铬酸吡啶 作用下， 以 癸烷 、 苯 为溶剂， 反应 16.0h， 生成 (1R*,8aR*)-1,8a-dimethyl-1,7,8,8a-tetrahydronaphthalene-2,6-dione
  参考文献：
  名称：

  Total Syntheses and Biological Evaluation of (±)-Botryosphaeridione, (±)-Pleodendione, 4-epi-Periconianone B, and Analogues

  摘要：

  The total syntheses of (+/-)-botryosphaeridione, (+/-)-pleodendione, (+/-)-hoaensieremodione, 4-epi-periconianone B, and their analogues have been accomplished for the first time. All the synthesized target compounds were screened in neural anti-inflammatory assays using LPS induced microglia cells (N9). Among them, compounds 1 and 21 were identified as potential lead compounds for further profiling.

  DOI：

  10.1021/acsmedchemlett.5b00241
• 作为产物：
  描述：

  在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以65%的产率得到(4aR,5S)-4a,5-dimethyl-4,4a,5,6-tetrahydronaphthalen-2(3H)-one
  参考文献：
  名称：

  Total Syntheses and Biological Evaluation of (±)-Botryosphaeridione, (±)-Pleodendione, 4-epi-Periconianone B, and Analogues

  摘要：

  The total syntheses of (+/-)-botryosphaeridione, (+/-)-pleodendione, (+/-)-hoaensieremodione, 4-epi-periconianone B, and their analogues have been accomplished for the first time. All the synthesized target compounds were screened in neural anti-inflammatory assays using LPS induced microglia cells (N9). Among them, compounds 1 and 21 were identified as potential lead compounds for further profiling.

  DOI：

  10.1021/acsmedchemlett.5b00241

文献信息

• Neural Anti-Inflammatory Natural Product Periconianone A: Total Synthesis and Biological Evaluation
  作者：Hanuman P. Kalmode、Suhag S. Patil、Kishor L. Handore、Paresh R. Athawale、Rambabu Dandela、Abhishek Kumar Verma、Anirban Basu、D. Srinivasa Reddy

  DOI：10.1002/ejoc.201900048

  日期：2019.4.9

  Total synthesis of periconianone A, an eremophilane‐type sesquiterpenoid with impressive neural anti‐inflammatory potential, has been accomplished. Diels–Alder/aldol strategy to construct tetrahydro‐naphthalene‐2,6‐dione scaffold, allylic oxidation of dienone using DBU/O2 and postulated biomimetic aldol reaction to construct 6/6/6 tricyclic system are the highlights of the present synthesis.

  Periconianone A是一种具有令人印象深刻的神经抗炎潜能的艾美金刚型倍半萜类化合物的全合成。Diels-Alder / aldol策略构建四氢萘-2,6-dione支架，使用DBU / O 2进行二烯酮的烯丙基氧化和拟仿生醛醇缩合反应以构建6/6/6三环系统是本合成的重点。
• Enantioselective synthesis of R-(−)-ligularenolide starting from S-(+)-carvone
  作者：Louis H.D Jenniskens、Aede de Groot

  DOI：10.1016/s0040-4039(97)01757-7

  日期：1997.10

  The first enantioselective synthesis of R-(−)-ligularenolide 1 starting from S-(+)-carvone 2 is described.

  描述了从S-（+）-香芹酮2开始的R-（-）-木香烯内酯1的第一对映选择性合成。
• Enantioselective synthesis of R-(−)-ligularenolide and the progesterone receptor ligand R-(−)-PF1092C starting from S-(+)-carvone
  作者：Louis H.D. Jenniskens、Aede de Groot

  DOI：10.1016/s0040-4020(98)00233-6

  日期：1998.5

  enantioselective synthesis of eremophilane sesquiterpenes was developed starting from S-(+)-carvone 3, using a conjugate addition-annelation sequence. The synthesis of R-(−)-ligularenolide 1 was accomplished in a staightforward manner with the annelation of the lactone as the last step. For the synthesis of the progesterone receptor ligand R-(−)-PF1092C 2 a different strategy was followed in which first the lactone

  从S-（+）-香芹酮3开始，使用共轭加成-退火序列，开发了一种新的对映体选择性的全草胺倍半萜。R-（-）-叶烯醇内酯1的合成以固定的方式完成，最后一步是内酯的内环化。为了合成孕酮受体配体R-（-）-PF1092C 2，采用了不同的策略，其中首先将内酯退火。异丙烯基双键进入共轭位置的伴随异构化随后提供了另一种去除侧链的方法，同时为在C2，C3位置引入顺式β-二醇功能提供了理想的功能。
• Total Syntheses and Biological Evaluation of (±)-Botryosphaeridione, (±)-Pleodendione, 4-<i>epi</i>-Periconianone B, and Analogues
  作者：Kishor L. Handore、Prakash D. Jadhav、Bibhabasu Hazra、Anirban Basu、D. Srinivasa Reddy

  DOI：10.1021/acsmedchemlett.5b00241

  日期：2015.11.12

  The total syntheses of (+/-)-botryosphaeridione, (+/-)-pleodendione, (+/-)-hoaensieremodione, 4-epi-periconianone B, and their analogues have been accomplished for the first time. All the synthesized target compounds were screened in neural anti-inflammatory assays using LPS induced microglia cells (N9). Among them, compounds 1 and 21 were identified as potential lead compounds for further profiling.