3,5-dimethyl-1-(carbethoxymethylene)cyclohexane | 85120-26-9

• 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: 3,5-dimethyl-1-(carbethoxymethylene)cyclohexane
• 英文别名: (3,5-dimethyl-cyclohexyliden)-acetic acid ethyl ester；(3,5-Dimethyl-cyclohexyliden)-essigsaeure-aethylester；ethyl 3,5-dimethyl-cyclohexylideneacetate；ethyl 2-(3,5-dimethylcyclohexylidene)acetate
• CAS: 85120-26-9
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: LOIOUEKABHAYLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-dimethyl-1-(carbethoxymethylene)cyclohexane 在 Ra-Ni 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 35.0~70.0 ℃ 、275.79 kPa 条件下， 反应 36.0h， 生成 (5S,7R,9S)-7,9-Dimethyl-2-aza-spiro[4.5]decan-3-one
  参考文献：
  名称：

  Identification of Novel Ligands for the Gabapentin Binding Site on the α₂δ Subunit of a Calcium Channel and Their Evaluation as Anticonvulsant Agents

  摘要：

  As part of a program to investigate the structure-activity relationships of Gabapentin (Neurontin), a number of alkylated analogues were synthesized and evaluated in vitro for binding to the Gabapentin binding site located on the alpha(2) delta subunit of a calcium channel. A number of other bridged and heterocyclic analogues are also reported along with their in vitro data. Two compounds showing higher affinity than Gabapentin were selected for evaluation in an animal model of epilepsy. One of these compounds, cis-(1S,3R)-(1-(aminomethyl)-3-methylcyclohexyl)acetic acid hydrochloride (19), was shown to be effective in this model with a profile similar to that of Gabapentin itself.

  DOI：

  10.1021/jm970649n
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 顺式-3,5-二甲基环己酮 在 sodium hydride 作用下， 生成 3,5-dimethyl-1-(carbethoxymethylene)cyclohexane
  参考文献：
  名称：

  Identification of Novel Ligands for the Gabapentin Binding Site on the α₂δ Subunit of a Calcium Channel and Their Evaluation as Anticonvulsant Agents

  摘要：

  As part of a program to investigate the structure-activity relationships of Gabapentin (Neurontin), a number of alkylated analogues were synthesized and evaluated in vitro for binding to the Gabapentin binding site located on the alpha(2) delta subunit of a calcium channel. A number of other bridged and heterocyclic analogues are also reported along with their in vitro data. Two compounds showing higher affinity than Gabapentin were selected for evaluation in an animal model of epilepsy. One of these compounds, cis-(1S,3R)-(1-(aminomethyl)-3-methylcyclohexyl)acetic acid hydrochloride (19), was shown to be effective in this model with a profile similar to that of Gabapentin itself.

  DOI：

  10.1021/jm970649n
• 作为试剂：
  描述：

  钠 、 磷酰基乙酸三乙酯 、 3,5-二甲基环己酮 、 在 甲苯 、 3,5-dimethyl-1-(carbethoxymethylene)cyclohexane 作用下， 以 甲苯 为溶剂， 反应 53.0h， 生成 3,5-dimethyl-1-(carbethoxymethylene)cyclohexane
  参考文献：
  名称：

  Odorant substances

  摘要：

  新的芳香化合物，特别是具有以下式子的化合物：##STR1## 其中R是具有以下式子的脂肪族残基：##STR2## 其中R.sup.1是C.sub.1-4烷基，C.sub.1-4烷基亚甲基或C.sub.2-4烯基，这些残基中碳原子的总数为2到5，m和n等于零或1，p为1、2或3，点线表示一个或两个可选的双键。本发明还涉及一种制备新的二酮I的方法，以及将I用作气味化合物在气味组合物中的使用，该组合物具有一定比例的具有式I的化合物。

  公开号：

  US04457862A1

文献信息

• Enantioselective Wittig-Horner reaction in the solid state
  作者：Fumio Toda、Hiroshi Akai

  DOI：10.1021/jo00298a010

  日期：1990.5
• TODA, FUMIO;AKAI, HIROSHI, J. ORG. CHEM., 55,(1990) N1, C. 3446-3447
  作者：TODA, FUMIO、AKAI, HIROSHI

  DOI：——

  日期：——
• US4457862A
  申请人：——

  公开号：US4457862A

  公开（公告）日：1984-07-03
• Odorant substances
  申请人：Givaudan Corporation

  公开号：US04457862A1

  公开（公告）日：1984-07-03

  New odoriferous compounds, particularly the compounds having the following formula: ##STR1## wherein R is an aliphatic residue having the formula ##STR2## wherein R.sup.1 is a C.sub.1-4 alkyl, C.sub.1-4 alkylidene or C.sub.2-4 alkenyl, the sum of the carbon atoms being in those residues from 2 to 5, m and n being equal to zero or 1, p being 1, 2 or 3 and the dotted lines representing one or two optional double bonds. The invention also relates to a method for the preparation of new di-ketones I: as well as the use of I as odoriferous compounds in odoriferous compositions, which are characterized by a certain proportion of compounds having the formula I.

  新的芳香化合物，特别是具有以下结构的化合物：##STR1## 其中R是具有以下结构的脂肪残基##STR2## 其中R.sup.1是C.sub.1-4烷基，C.sub.1-4烷基亚甲基或C.sub.2-4烯基，这些残基中碳原子的总数为2到5，m和n等于零或1，p为1、2或3，虚线代表一个或两个可选的双键。该发明还涉及一种制备新的二酮I的方法：以及将I用作芳香化合物的气味组合物中的用途，其特点是含有具有公式I的化合物的一定比例。
• Identification of Novel Ligands for the Gabapentin Binding Site on the α₂δ Subunit of a Calcium Channel and Their Evaluation as Anticonvulsant Agents
  作者：Justin S. Bryans、Natasha Davies、Nicolas S. Gee、Visaka U. K. Dissanayake、Giles S. Ratcliffe、David C. Horwell、Clare O. Kneen、Andrew I. Morrell、Ryszard J. Oles、John C. O'Toole、Gemma M. Perkins、Lakhbir Singh、Nirmala Suman-Chauhan、Jacqueline A. O'Neill

  DOI：10.1021/jm970649n

  日期：1998.5.1

  As part of a program to investigate the structure-activity relationships of Gabapentin (Neurontin), a number of alkylated analogues were synthesized and evaluated in vitro for binding to the Gabapentin binding site located on the alpha(2) delta subunit of a calcium channel. A number of other bridged and heterocyclic analogues are also reported along with their in vitro data. Two compounds showing higher affinity than Gabapentin were selected for evaluation in an animal model of epilepsy. One of these compounds, cis-(1S,3R)-(1-(aminomethyl)-3-methylcyclohexyl)acetic acid hydrochloride (19), was shown to be effective in this model with a profile similar to that of Gabapentin itself.