methyl 4-(2-oxoethylidene)cyclohexane-1-carboxylate | 116289-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-(2-oxoethylidene)cyclohexane-1-carboxylate
• 英文别名: Methyl 4-(2-Oxoethylidene)cyclohexanecarboxylate；methyl 4-(oxoethylidene)-cyclohexanecarboxylate；methyl 4-(oxoethylidene)cyclohexanecarboxylate
• CAS: 116289-14-6
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: ACQIWILGWWZQMH-VURMDHGXSA-N

物化性质

• 沸点：
  281.9±33.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 4-(2-oxoethylidene)cyclohexane-1-carboxylate 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 sodium tetrahydroborate 、 草酰氯 、 D-(-)-酒石酸二乙酯 、 potassium tert-butylate 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 53.17h， 生成 Methyl <4(R)-<1α,4β,4(Z)>>-4-hydroxy-4-<1-<(2-methoxy-2-oxoethyl)thio>-2-hexadecenyl>cyclohexanecarboxylate
  参考文献：
  名称：

  Conformationally restricted leukotriene antagonists. Synthesis of chiral 4-hydroxy-4-alkylcyclohexanecarboxylic acids as leukotriene D4 analogs

  摘要：

  Eight conformationally restricted LTD4 analogues, 2a-d (n = 1, 2), were prepared in nine steps from methyl 4-hydroxybenzoate (3). The key step in this approach is the Sharpless asymmetric epoxidation of allylic alcohol 8 in which all four possible epoxy alcohol diastereomers 9a-d were prepared. A single-crystal X-ray analysis of 9b and application of the Sharpless model for predicting epoxidation stereoselectivity led to the assignment of relative stereochemistry and absolute configuration of 9a-d. These high optical purity epoxy alcohols were then converted to chiral LTD4 analogues 2a-d (n = 1, 2) in three steps.

  DOI：

  10.1021/jo00005a019
• 作为产物：
  描述：

  4-羟基环己甲酸甲酯 在 Celite 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 乙腈 为溶剂， 反应 3.5h， 生成 methyl 4-(2-oxoethylidene)cyclohexane-1-carboxylate
  参考文献：
  名称：

  Conformationally restricted leukotriene antagonists. Synthesis of chiral 4-hydroxy-4-alkylcyclohexanecarboxylic acids as leukotriene D4 analogs

  摘要：

  Eight conformationally restricted LTD4 analogues, 2a-d (n = 1, 2), were prepared in nine steps from methyl 4-hydroxybenzoate (3). The key step in this approach is the Sharpless asymmetric epoxidation of allylic alcohol 8 in which all four possible epoxy alcohol diastereomers 9a-d were prepared. A single-crystal X-ray analysis of 9b and application of the Sharpless model for predicting epoxidation stereoselectivity led to the assignment of relative stereochemistry and absolute configuration of 9a-d. These high optical purity epoxy alcohols were then converted to chiral LTD4 analogues 2a-d (n = 1, 2) in three steps.

  DOI：

  10.1021/jo00005a019

文献信息

• 4-hydroxy-4-(substituted alkenyl)cyclohexanecarboxylic acids
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US04748274A1

  公开（公告）日：1988-05-31

  The present invention relates to compounds which are 4-hydroxy-4-alkenylcyclohexanecarboxylic acid derivatives possessing leukotriene antagonist activity. The compounds are useful in the treatment of allergic diseases, particularly in the treatment of human asthma. They are prepared by the reaction of an appropriate oxaspiro compound with a mercaptoalkanoic acid derivative.

  本发明涉及具有白三烯拮抗活性的4-羟基-4-烯基环己烷羧酸衍生物化合物。这些化合物在过敏性疾病的治疗中很有用，特别是在人类哮喘的治疗中。它们通过将适当的氧杂螺环化合物与巯基烷酸衍生物反应制备而成。
• 4-Hydroxy-4-(substituted alkenyl)-cyclohexane carboxylic acid
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0270843B1

  公开（公告）日：1991-03-06
• CREGGE, ROBERT J.;LENTZ, NELSEN L.;SABOL, JEFFREY S., J. ORG. CHEM., 56,(1991) N, C. 1758-1763
  作者：CREGGE, ROBERT J.、LENTZ, NELSEN L.、SABOL, JEFFREY S.

  DOI：——

  日期：——
• US4748274A
  申请人：——

  公开号：US4748274A

  公开（公告）日：1988-05-31
• Conformationally restricted leukotriene antagonists. Synthesis of chiral 4-hydroxy-4-alkylcyclohexanecarboxylic acids as leukotriene D4 analogs
  作者：Robert J. Cregge、Nelsen L. Lentz、Jeffrey S. Sabol

  DOI：10.1021/jo00005a019

  日期：1991.3

  Eight conformationally restricted LTD4 analogues, 2a-d (n = 1, 2), were prepared in nine steps from methyl 4-hydroxybenzoate (3). The key step in this approach is the Sharpless asymmetric epoxidation of allylic alcohol 8 in which all four possible epoxy alcohol diastereomers 9a-d were prepared. A single-crystal X-ray analysis of 9b and application of the Sharpless model for predicting epoxidation stereoselectivity led to the assignment of relative stereochemistry and absolute configuration of 9a-d. These high optical purity epoxy alcohols were then converted to chiral LTD4 analogues 2a-d (n = 1, 2) in three steps.