3-methylenecyclohexanecarboxylic acid | 98043-32-4

• 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: 3-methylenecyclohexanecarboxylic acid
• 英文别名: 3-Methylidenecyclohexane-1-carboxylic acid
• CAS: 98043-32-4
• 化学式: C₈H₁₂O₂
• mdl: MFCD19228790
• 分子量: 140.182
• InChiKey: DQJUDESTYLTGIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  49-50 °C(Solv: hexane (110-54-3); dichloromethane (75-09-2))
• 沸点：
  252.4±19.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methylenecyclohexanecarboxylic acid 在 氢氧化钾 、 对甲苯磺酸 、 二异丙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 52.5h， 生成 8-hydroxy-5-hydroxymethyl-3,6-dioxatricyclo[6.3.1.0^1,5]dodecan-2-one
  参考文献：
  名称：

  Hydrogen-bonding patterns of two dihydroxylactone derivatives

  摘要：

  In the hydrogen-bonding networks of 8-hydroxy-5-hydroxymethyl-3,6-dioxatricyclo[6.3.1.0(1.5)]dodecan-2-one and 5,7-bis(hydroxymethyl)-3,6-dioxatricyclo [5.3.1.0(1.5)] undecan-2-one, both C11H16O5, layers and double strands, respectively, lead to the formation of chains connected by hydroxy-to-hydroxy contacts, where the hydroxymethyl group, present in both structures, acts as a donor. The secondary structures differ in the hydrogen bonding of these chains via the second hydroxy group, which is involved in hydroxy-to-carbonyl and hydroxy-to-hydroxy bonds, respectively.

  DOI：

  10.1107/s0108270105000557
• 作为产物：
  描述：

  3-氧代-环己烷羧酸甲酯 在 氢氧化钾 、 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.5h， 生成 3-methylenecyclohexanecarboxylic acid
  参考文献：
  名称：

  均相加氢中羧酸根的立体化学控制

  摘要：

  已经研究了一系列不饱和环己烷羧酸及其酯的氢化立体化学，采用基于CH 2 Cl 2的双（1,4-二苯基膦基）丁铵或吡啶（三环己基膦基）铱基阳离子催化剂。对于3-甲基环己-2-烯甲酸甲酯，在两种情况下都实现了对反式产物的高度选择性还原，而异构体3-亚甲基环己烷甲酸甲酯给出了相当数量的顺式异构体。在相当慢的反应中，在还原4-甲基环己-3-烯丙基羧酸甲酯方面也获得了反式异构体的优势。D 2的还原 揭示了在氢化过程中发生了烯烃双键的相当大的异构化。

  DOI：

  10.1016/0022-328x(85)87378-2

文献信息

• SUBSTITUTED ANILINES AS CCR(4) ANTAGONISTS
  申请人：ChemoCentryx, Inc.

  公开号：US20150141397A1

  公开（公告）日：2015-05-21

  Aniline compounds are provided which bind to CCR(4) and are useful for the treatment of diseases such as allergic diseases, autoimmune diseases, graft rejection and cancer.

  提供结合CCR(4)的苯胺化合物，可用于治疗过敏性疾病、自身免疫性疾病、移植排斥和癌症等疾病。
• Synthesis and Structure of Hydroxyl Acids of General Structure 7,7-Alkenyl/alkynyl-5-hydroxymethyl-6-oxabicyclo[3.2.1]octane- 1-carboxylic Acid
  作者：Natalia Pérez-Hernández、Martín Febles、Cirilo Pérez、Ricardo Pérez、Matías L. Rodríguez、Concepción Foces-Foces、Julio D. Martín

  DOI：10.1021/jo052237p

  日期：2006.2.1

  [Graphics]The open-ended hollow tubular structure formed by inclusion of water molecules in the packing of the hydroxyl acid 1 (R-1 = CH2OH, R-2 = ethyl groups) led to the synthesis and structural study of their unsaturated analogues. In this article we report on a general and practical large-scale synthesis of hydroxyl acids that possess alkenyl and alkynyl appendages. Substitution of the ethyl groups in I with unsaturated two-carbon appendages has a different effect on the molecular structure and on the hydrogen-bonding pattern. No variation has been induced by Substitution of only one ethyl group with a vinyl one, although the substitution of both ethyl groups with vinyl or acetylene appendages has the greatest effect on the molecular structure and results in different hydrogen-bonding motifs.
• Hydrogen-bonding patterns of two dihydroxylactone derivatives
  作者：M. L. Rodríguez、M. Febles、C. Pérez、N. Pérez-Hernández、J. D. Martín、C. Foces-Foces

  DOI：10.1107/s0108270105000557

  日期：2005.3.15

  In the hydrogen-bonding networks of 8-hydroxy-5-hydroxymethyl-3,6-dioxatricyclo[6.3.1.0(1.5)]dodecan-2-one and 5,7-bis(hydroxymethyl)-3,6-dioxatricyclo [5.3.1.0(1.5)] undecan-2-one, both C11H16O5, layers and double strands, respectively, lead to the formation of chains connected by hydroxy-to-hydroxy contacts, where the hydroxymethyl group, present in both structures, acts as a donor. The secondary structures differ in the hydrogen bonding of these chains via the second hydroxy group, which is involved in hydroxy-to-carbonyl and hydroxy-to-hydroxy bonds, respectively.
• Stereochemical control by carboxylate groups in homogeneous hydrogenation
  作者：John M. Brown、Stephen A. Hall

  DOI：10.1016/0022-328x(85)87378-2

  日期：1985.4

  The stereochemistry of hydrogenation of a range of unsaturated cyclohexanecarboxylic acids and their esters has been investigated, employing either bis(1,4-diphenylphosphino)butanerhodium or pyridine(tricyclohexylphosphine)iridium based cationic catalysts in CH2Cl2. For methyl 3-methylcyclohex-2-enecarboxylate, highly selective reduction to the trans-product was achieved in both cases, whereas the

  已经研究了一系列不饱和环己烷羧酸及其酯的氢化立体化学，采用基于CH 2 Cl 2的双（1,4-二苯基膦基）丁铵或吡啶（三环己基膦基）铱基阳离子催化剂。对于3-甲基环己-2-烯甲酸甲酯，在两种情况下都实现了对反式产物的高度选择性还原，而异构体3-亚甲基环己烷甲酸甲酯给出了相当数量的顺式异构体。在相当慢的反应中，在还原4-甲基环己-3-烯丙基羧酸甲酯方面也获得了反式异构体的优势。D 2的还原 揭示了在氢化过程中发生了烯烃双键的相当大的异构化。