4-[bis(methoxycarbonyl)methyl]cyclohexanone | 1227734-49-7

• 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: 4-[bis(methoxycarbonyl)methyl]cyclohexanone
• 英文别名: dimethyl (4-oxocyclohexyl)malonate；dimethyl 2-(4-oxocyclohexyl)propanedioate
• CAS: 1227734-49-7
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: MJDBKQNGPYTJCR-UHFFFAOYSA-N

物化性质

• 熔点：
  59-60 °C
• 沸点：
  306.5±12.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[bis(methoxycarbonyl)methyl]cyclohexanone 、 adamantan-2-one O-methyloxime 在 碳酸氢钠 、 臭氧 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 2.0h， 以75%的产率得到cis-adamantane-2-spiro-3'-8'-[bis(methoxycarbonyl)methyl]-1',2',4'-trioxaspiro[4.5]decane
  参考文献：
  名称：

  Structure−Activity Relationship of an Ozonide Carboxylic Acid (OZ78) againstFasciola hepatica

  摘要：

  In this paper, we describe the SAR of ozonide carboxylic acid OZ78 (1) as the first part of our search for a trematocidal synthetic peroxide drug development candidate. We found that relatively small structural changes to 1 resulted most commonly in loss of activity against Fasciola hepatica in vivo. A spiro-adamantane substructure and acidic functional group (or ester prodrug) were required for activity. Of 26 new compounds administered at single 100 mg/kg oral doses to F. hepatica infected rats, 8 had statistically significant worm burden reductions, 7 were partially curative, and 1 (acylsulfonamide 6) was completely curative and comparable to 1 in flukicidal efficacy. This study also showed that the activity of 1 is peroxide-bond-dependent, suggesting that its flukicidal efficacy depends upon hemoglobin digestion in F. hepatica.

  DOI：

  10.1021/jm100226t
• 作为产物：
  描述：

  dimethyl 2-[4-(benzyloxy)benzyl]malonate 在 Pd/Al₂O₃ 、 氢气 作用下， 以 1,2-二氯乙烷 为溶剂， 60.0 ℃ 、500.01 kPa 条件下， 反应 24.0h， 生成 4-[bis(methoxycarbonyl)methyl]cyclohexanone
  参考文献：
  名称：

  钴催化环外烯烃的不对称异构化

  摘要：

  手性环状烯烃（1-甲基环己烯）是用于合成药物和天然产物的多功能构件。尽管这些结构基序很普遍，但开发有效的合成方法仍然是一个未解决的挑战。在此，我们报道了一种使用一系列新设计的手性钴催化剂对环外烯烃进行新型不对称异构化，从而可以直接构建具有多种功能的手性 1-甲基环己烯。该方法的合成效用通过对天然产物 β-红没药烯的简明和对映选择性合成突出。多种衍生化进一步证明了反应产物的多功能性。

  DOI：

  10.1021/jacs.1c11343

文献信息

• Substituted cyclohexylaminopyrimidines
  申请人：Hoechst Schering Agrevo

  公开号：US06197729B1

  公开（公告）日：2001-03-06

  Compounds of formula I where R1 is hydrogen, chlorine, fluorine or methyl, R2 and R3, which may be the same or different from each other, are hydrogen, halogen, cyano, (C1-C4)-alkyl, vinyl, ethynyl, (C1-C4)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl, fluorovinyl or fluoroethyl, or R2 and R3 together with the linking carbon atoms form a benzo ring, and R4 is (C2-C4)-alkyl, (C2-C4)-alkenyl or (C3-C4)-alkinyl, each of which is substituted by at least two fluorine atoms and optionally substituted by C1-4-alkoxy, cyanomethoxy, (C3-C4)-alkenyloxy or (C3-C4)-alkinyloxy, are useful as pesticides, especially against insects, acarids and fungi. The invention includes a novel process for fluorinating certain pyrimidines.

  化学式I的化合物，其中R1是氢、氯、氟或甲基，R2和R3可以相同也可以不同，分别是氢、卤素、氰基、(C1-C4)-烷基、乙烯基、乙炔基、(C1-C4)-烷氧基、(C1-C4)-烷氧基-(C1-C4)-烷基、氟乙烯基或氟乙基，或者R2和R3与连接碳原子一起形成苯环，而R4是(C2-C4)-烷基、(C2-C4)-烯基或(C3-C4)-炔基，每个都至少被两个氟原子取代，并且可选地被C1-4-烷氧基、氰甲氧基、(C3-C4)-烯氧基或(C3-C4)-炔氧基取代，这些化合物可用作杀虫剂，特别是对抗昆虫、螨虫和真菌。该发明包括一种新颖的对某些嘧啶类化合物进行氟化的方法。
• Structure−Activity Relationship of an Ozonide Carboxylic Acid (OZ78) against<i>Fasciola hepatica</i>
  作者：Qingjie Zhao、Mireille Vargas、Yuxiang Dong、Lin Zhou、Xiaofang Wang、Kamaraj Sriraghavan、Jennifer Keiser、Jonathan L. Vennerstrom

  DOI：10.1021/jm100226t

  日期：2010.5.27

  In this paper, we describe the SAR of ozonide carboxylic acid OZ78 (1) as the first part of our search for a trematocidal synthetic peroxide drug development candidate. We found that relatively small structural changes to 1 resulted most commonly in loss of activity against Fasciola hepatica in vivo. A spiro-adamantane substructure and acidic functional group (or ester prodrug) were required for activity. Of 26 new compounds administered at single 100 mg/kg oral doses to F. hepatica infected rats, 8 had statistically significant worm burden reductions, 7 were partially curative, and 1 (acylsulfonamide 6) was completely curative and comparable to 1 in flukicidal efficacy. This study also showed that the activity of 1 is peroxide-bond-dependent, suggesting that its flukicidal efficacy depends upon hemoglobin digestion in F. hepatica.
• Cobalt-Catalyzed Desymmetric Isomerization of Exocyclic Olefins
  作者：Xufang Liu、Xianle Rong、Shihan Liu、Yu Lan、Qiang Liu

  DOI：10.1021/jacs.1c11343

  日期：2021.12.15

  Chiral cyclic olefins, 1-methylcyclohexenes, are versatile building blocks for the synthesis of pharmaceuticals and natural products. Despite the prevalence of these structural motifs, the development of efficient synthetic methods remains an unmet challenge. Herein we report a novel desymmetric isomerization of exocyclic olefins using a series of newly designed chiral cobalt catalysts, which enables

  手性环状烯烃（1-甲基环己烯）是用于合成药物和天然产物的多功能构件。尽管这些结构基序很普遍，但开发有效的合成方法仍然是一个未解决的挑战。在此，我们报道了一种使用一系列新设计的手性钴催化剂对环外烯烃进行新型不对称异构化，从而可以直接构建具有多种功能的手性 1-甲基环己烯。该方法的合成效用通过对天然产物 β-红没药烯的简明和对映选择性合成突出。多种衍生化进一步证明了反应产物的多功能性。