4-acetyl-3,5,5-trimethylcyclohex-2-enone | 36433-01-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetyl-3,5,5-trimethylcyclohex-2-enone
• 英文别名: 3,5,5-Trimethyl-4-acetyl-2-cyclohexen-1-on；α-cyclocitral；4-Acetyl-3,5,5-trimethylcyclohex-2-en-1-one
• CAS: 36433-01-9
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: CUBVKAWHVIABMV-UHFFFAOYSA-N

物化性质

• 沸点：
  273.9±40.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-acetyl-3,5,5-trimethylcyclohex-2-enone 在 sodium hydroxide 、 sodium tetrahydroborate 、 jones reagent 、 cerium(III) chloride 作用下， 以 甲醇 、 乙醇 、 水 、 丙酮 为溶剂， 反应 9.58h， 生成 E-2,6,6-trimethyl-4-(3-phenylacryloyl)cyclohex-2-enone
  参考文献：
  名称：

  Synthesis of Active Antifeedant CDE Fragments of 11-Ketoepoxyazadiradione Based on an Electrocyclization Reaction Catalyzed by Perchloric Acid

  摘要：

  A synthetic route to mimics of the insect antifeedant epoxyazadiradione containing the CDE molecular fragment with an oxygenated function on ring C has been developed. The key step is based on a 2,6-diene-1,5-dione electrocyclization reaction catalyzed by perchloric acid, The rearrangement of the epoxy alcohol epimers 12 and 19 induced by acids deserves special mention. Several of the compounds obtained show significant antifeedant activity against Spodoptera frugiperda.

  DOI：

  10.1021/jo981456q
• 作为产物：
  描述：

  4-甲基-3戊烯-2-酮 、 乙酰丙酮 在 三氟化硼乙醚 作用下， 生成 4-acetyl-3,5,5-trimethylcyclohex-2-enone
  参考文献：
  名称：

  功能导向合成应用于抗肉毒杆菌天然产物川楝素

  摘要：

  肉毒杆菌神经毒素 (BoNT) 是导致肉毒杆菌中毒的病原体，肉毒杆菌中毒是一种以周围神经肌肉阻滞为特征的疾病，是人类特有的弛缓性麻痹。天然产物川楝素是一种传统中药，据报道在动物模型中具有抗肉毒杆菌的特性。为了确定在川楝素中发现的抗肉毒杆菌特性需要哪些化学官能团，启动了一项研究，目的是使用面向功能的合成 (FOS) 作为一种策略，开始揭示川楝素强大的抗肉毒杆菌特性。从这些研究中提出了一种新的合成策略，允许获得 4-乙酰氧基 CD 片段类似物（14) 的川楝素，它是由亚甲基砜和乙酰丙酮分 14 个步骤获得的。还报告了对该片段的动物研究。

  DOI：

  10.1016/j.bmc.2008.12.042

文献信息

• HYDROGENATION OF ESTERS OR CARBONYL GROUPS WITH PHOSPHINO-OXIDE BASED RUTHENIUM COMPLEXES
  申请人：Saudan Lionel

  公开号：US20110190523A1

  公开（公告）日：2011-08-04

  The present invention relates to the field of catalytic hydrogenation and, more particularly, to the use of specific ruthenium catalysts or pre-catalysts in hydrogenation processes for the reduction of ketones, aldehydes, esters or lactones into their corresponding alcohols or diols respectively. The preferred catalysts are ruthenium complexes comprising a ligand of the type (N—N) type and a ligand of the type (P—PO).

  本发明涉及催化加氢领域，更具体地涉及在加氢过程中使用特定的钌催化剂或前驱体，用于将酮、醛、酯或内酯还原为相应的醇或二醇。首选催化剂是包含(N—N)型配体和(P—PO)型配体的钌配合物。
• HYDROGENATION OF ESTER, KETONE OR ALDEHYDE GROUPS WITH RUTHENIUM COMPLEXES HAVING A DI-AMINE AND A PHOSPHOROUS-NITROGEN BIDENTATE LIGAND
  申请人：Firmenich S.A.

  公开号：EP2370207A1

  公开（公告）日：2011-10-05
• JPS5692240A
  申请人：——

  公开号：JPS5692240A

  公开（公告）日：1981-07-25
• [EN] HYDROGENATION OF ESTERS OR CARBONYL GROUPS WITH PHOSPHINO-OXIDE BASED RUTHENIUM COMPLEXES<br/>[FR] HYDROGÉNATION DE GROUPES ESTER OU CARBONYLE AVEC DES COMPLEXES DE RUTHÉNIUM À BASE D'OXYDE DE PHOSPHINE
  申请人：FIRMENICH & CIE

  公开号：WO2010038209A1

  公开（公告）日：2010-04-08

  The present invention relates to the field of catalytic hydrogenation and, more particularly, to the use of specific ruthenium catalysts, or pre-catalysts, in hydrogenation processes for the reduction of ketones, aldehydes and esters or lactones into the corresponding alcohol or diol respectively. Said catalysts are ruthenium complexes comprising a ligand of the type (N-N) type and a ligand of the type (P-PO).
• [EN] HYDROGENATION OF ESTER, KETONE OR ALDEHYDE GROUPS WITH RUTHENIUM COMPLEXES HAVING A DI-AMINE AND A PHOSPHOROUS-NITROGEN BIDENTATE LIGAND<br/>[FR] HYDROGÉNATION D'ESTERS, DE CÉTONES OU D'ALDÉHYDES AVEC DES COMPLEXES DE RUTHÉNIUM COMPORTANT UNE DIAMINE ET UN LIGAND BIDENTÉ PHOSPHORE-AZOTE
  申请人：FIRMENICH & CIE

  公开号：WO2010061350A1

  公开（公告）日：2010-06-03

  The present invention relates to the field of catalytic hydrogenation and, more particularly, to the use of specific ruthenium catalysts, or pre-catalysts, in hydrogenation processes with molecular H2 for the reduction of ketones, aldehydes and esters or lactones into the corresponding alcohol or diol respectively. Said catalysts are ruthenium complexes comprising a ligand of the type (N-N) type, in which at least one of said amino groups is a secondary or primary amine (i.e. a NH or NH2) and a ligand of the type (P-N) in which N belongs to a tertiary amino group, a N, N, N' trisubstituted carboxiamide (a C(=N)N moiety) or a N-substituted imidoate (a C(=N)O moiety).