1-乙酰基环戊烷羧酸 | 171924-95-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 1-乙酰基环戊烷羧酸
• 英文名称: 1-acetyl-1-cyclopentanecarboxylic acid
• 英文别名: 1-Acetylcyclopentane-1-carboxylic acid
• CAS: 171924-95-1
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: KGYWOXKHTNJTME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-乙酰基环戊烷羧酸 在 rhodium(II) acetate dimer 三乙胺 、 氯甲酸甲酯 作用下， 反应 5.0h， 生成 8,8-dimethoxy-7,10-epoxy-10-methyl-6-oxospiro<4,5>decane
  参考文献：
  名称：

  Generation and Cycloaddition Behavior of Spirocyclic Carbonyl Ylides. Application to the Synthesis of the Pterosin Family of Sesquiterpenes

  摘要：

  The Rh(II)-catalyzed reaction of 1-acetyl-1-(diazoacetyl)cyclopropane and ethyl 3-(1-acetyl-cyclopropyl)-2-diazo-3-oxopropiolate with various dipolarophiles afforded dipolar cycloadducts in good yield. The reaction involves the formation of a rhodium carbenoid and subsequent transannular cyclization of the electrophilic carbon onto the adjacent keto group to generate a five-membered cyclic carbonyl ylide which undergoes a subsequent dipolar cycloaddition reaction. The regiochemical results encountered can be rationalized on the basis of FMO considerations. For carbonyl ylides, the HOMO dipole is dominant for reactions with electron deficient dipolarophiles, while the LUMO becomes important for cycloaddition to more electron rich species. A short synthesis of several members of the pterosin family of sesquiterpenes is described in which the key step involves a dipolar cycloaddition using a carbonyl ylide. The Rh(II)-catalyzed reaction of 1-acetyl-1-(diazoacetyl)-cyclopropane with cyclopentenone afforded a dipolar cycloadduct in good yield as a 4:1 mixture of diastereomers. Treatment of the major cycloadduct with triphenylphosphonium bromide in the presence of sodium hydride gave the expected Wittig product. The reaction of this compound with acid in the presence of various solvents gave rise to several members of the pterosin family. The overall sequence of reactions can best be described as proceeding by an initial oxy-bridge ring opening followed by dehydration and a subsequent acid-catalyzed cyclopropyl ring opening. The facility of the process is undoubtedly related to the aromaticity gained in the final step.

  DOI：

  10.1021/jo951371e
• 作为产物：
  描述：

  甲基1-乙酰基环戊烷羧酸酯 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 1-乙酰基环戊烷羧酸
  参考文献：
  名称：

  Generation and Cycloaddition Behavior of Spirocyclic Carbonyl Ylides. Application to the Synthesis of the Pterosin Family of Sesquiterpenes

  摘要：

  The Rh(II)-catalyzed reaction of 1-acetyl-1-(diazoacetyl)cyclopropane and ethyl 3-(1-acetyl-cyclopropyl)-2-diazo-3-oxopropiolate with various dipolarophiles afforded dipolar cycloadducts in good yield. The reaction involves the formation of a rhodium carbenoid and subsequent transannular cyclization of the electrophilic carbon onto the adjacent keto group to generate a five-membered cyclic carbonyl ylide which undergoes a subsequent dipolar cycloaddition reaction. The regiochemical results encountered can be rationalized on the basis of FMO considerations. For carbonyl ylides, the HOMO dipole is dominant for reactions with electron deficient dipolarophiles, while the LUMO becomes important for cycloaddition to more electron rich species. A short synthesis of several members of the pterosin family of sesquiterpenes is described in which the key step involves a dipolar cycloaddition using a carbonyl ylide. The Rh(II)-catalyzed reaction of 1-acetyl-1-(diazoacetyl)-cyclopropane with cyclopentenone afforded a dipolar cycloadduct in good yield as a 4:1 mixture of diastereomers. Treatment of the major cycloadduct with triphenylphosphonium bromide in the presence of sodium hydride gave the expected Wittig product. The reaction of this compound with acid in the presence of various solvents gave rise to several members of the pterosin family. The overall sequence of reactions can best be described as proceeding by an initial oxy-bridge ring opening followed by dehydration and a subsequent acid-catalyzed cyclopropyl ring opening. The facility of the process is undoubtedly related to the aromaticity gained in the final step.

  DOI：

  10.1021/jo951371e

文献信息

• [EN] NEW PROCESS FOR THE PREPARATION OF 2-CYCLOPENTYL-6-METHOXY-ISONICOTINIC ACID<br/>[FR] NOUVEAU PROCÉDÉ DE PRÉPARATION D'ACIDE 2-CYCLOPENTYL-6-MÉTHOXY-ISONICOTINIQUE
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2013175397A1

  公开（公告）日：2013-11-28

  The present invention relates to new processes for the preparation of 2-cyclopentyl-6-methoxy-isonicotinic acid, which is a useful intermediate for the synthesis of pyridine-4-yl derivatives as immunomodulating agent. Moreover, the present invention also relates to new intermediates used in those processes.

  本发明涉及一种制备2-环戊基-6-甲氧基吡啶-4-基甲酸的新工艺，该化合物是合成吡啶-4-基衍生物作为免疫调节剂的有用中间体。此外，本发明还涉及用于这些工艺的新中间体。
• NEW PROCESS FOR THE PREPARATION OF 2-CYCLOPENTYL-6-METHOXY-ISONICOTINIC ACID
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：US20150133669A1

  公开（公告）日：2015-05-14

  The present invention relates to new processes for the preparation of 2-cyclopentyl-6-methoxy-isonicotinic acid, which is a useful intermediate for the synthesis of pyridine-4-yl derivatives as immunomodulating agent. Moreover, the present invention also relates to new intermediates used in those processes.

  本发明涉及制备2-环戊基-6-甲氧基异烟酸的新工艺，该化合物是合成吡啶-4-基衍生物免疫调节剂的有用中间体。此外，本发明还涉及在这些工艺中使用的新中间体。
• Novel complex amido and imido derivatives of carboxyalkyl peptides and thioethers and ethers of peptides
  申请人：Ryan, James Walter

  公开号：EP0073143A2

  公开（公告）日：1983-03-02

  Novel inhibitors of angiotensin converting enzyme are disclosed which have the general formula wherein R, and/or R3 form complex amides and imides thereof, X = S, O or NR3, R4 and Rs form with -N-C- a 4-6 membered ring structure as described and the other R substituents are selected from a variety of disclosed groups.

  已公开的新型血管紧张素转换酶抑制剂具有通式 其中 R 和/或 R3 形成其复合酰胺和亚胺，X = S、O 或 NR3，R4 和 Rs 与 -N-C- 形成所述的 4-6 分子环结构，其他 R 取代基选自各种已公开的基团。
• Process for producing alpha,beta-unsaturated ketones
  申请人：NIPPON ZEON CO., LTD.

  公开号：EP0133548A1

  公开（公告）日：1985-02-27

  A process for producing alpha, beta-unsaturated ketones represented by the following general formula wherein R, represents a hydrocarbon radical, R2 represents an organic radical bonded through a carbon-carbon bond, R3 and R4 represent a hydrogen atom or a hydrocarbon radical, and R1, R2, R3 and R4 may be straight-chained or form a ring in arbitrary combinations, which comprises contacting an alpha-disubstituted-beta-keto acid ester represented by the general formula wherein R,, R2, R3 and R4 are as defined, and R5, R6, R7 and R8 represent a hydrogen atom or a hydrocarbon radical, with a catalyst consisting essentially of (a) a compound of a platinum-group metal and optionally (b) a monodentate ligand (b).

  一种生产由以下通式表示的α、β-不饱和酮的工艺 其中 R 代表烃基，R2 代表通过碳-碳键结合的有机基，R3 和 R4 代表氢原子或烃基，且 R1、R2、R3 和 R4 可以是直链或以任意组合形成环，该工艺包括与通式所代表的 α-二取代-β-酮酸酯接触 其中 R、R2、R3 和 R4 如所定义，R5、R6、R7 和 R8 代表氢原子或烃基，催化剂主要包括 (a) 铂族金属化合物和可选的 (b) 单齿配体 (b)。
• Curable compositions containing ethylenically unsaturated monomers, polyarylcyanate ester compositions and catalyst
  申请人：THE DOW CHEMICAL COMPANY

  公开号：EP0315089A2

  公开（公告）日：1989-05-10

  Polyarylcyanate compositions are cured by heating at a temperature of from 60°C to 100°C in the presence of, as a catalyst, 0.1 to 2 percent by weight of at least one iron, cobalt or zinc salt of a monocarboxylic acid based upon the combined weight of the polyarylcyanate and catalyst.

  聚芳基氰酸酯组合物的固化方法是：在 60°C 至 100°C 的温度下，在催化剂（以聚芳基氰酸酯和催化剂的总重量为基准）存在下，加热至少一种单羧酸铁盐、钴盐或锌盐（重量百分比为 0.1%至 2%）。