4-acetoxycycloheptanone | 24890-81-1

• 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-acetoxycycloheptanone
• 英文别名: (4-Oxocycloheptyl) acetate
• CAS: 24890-81-1
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: HFUKUPUEHYYXJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-acetoxycycloheptanone 在 咪唑 、 四丙基高钌酸铵 、 potassium tert-butylate 、 四丁基氟化铵 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [4-[(E)-1-Methyl-3-(2,6,6-trimethyl-cyclohex-1-enyl)-prop-2-en-(E)-ylidene]-cyclohept-(E)-ylidene]-acetaldehyde
  参考文献：
  名称：

  Absolute Sense of Twist of the C12C13 Bond of the Retinal Chromophore in Bovine Rhodopsin Based on Exciton-Coupled CD Spectra of 11,12-Dihydroretinal Analogues

  摘要：

  DOI：

  10.1002/anie.199720891
• 作为产物：
  描述：

  2-环庚烯-1-酮 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 氢气 、 甲基三辛基氯化铵 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 生成 4-acetoxycycloheptanone
  参考文献：
  名称：

  Absolute Sense of Twist of the C12C13 Bond of the Retinal Chromophore in Bovine Rhodopsin Based on Exciton-Coupled CD Spectra of 11,12-Dihydroretinal Analogues

  摘要：

  DOI：

  10.1002/anie.199720891

文献信息

• Intramolecular nucleophilic acyl substitution reactions of halo-substituted esters and lactones. New applications of organosamarium reagents
  作者：Gary A. Molander、Jeffrey A. McKie

  DOI：10.1021/jo00077a053

  日期：1993.12

  Intramolecular nucleophilic acyl substitution reactions involving a broad range of halo substituted carboxylic acid derivatives have been accomplished in excellent yield employing samarium(II) iodide as the reductive coupling agent. Although particular substrates cyclized most effectively in THF in the presence of tripiperidinophosphine oxide, carboxylic acid esters, the focus of this report, cyclize equally well without such an additive in the presence of a catalytic quantity of iron(III) complexes. Thus a comprehensive series of halo substituted esters were cyclized in excellent yield to the corresponding 4-, 5-, and 6-membered carbocycles. The reaction is extremely mild and selective as demonstrated by experiments wherein alkyl chlorides, acetals, and olefins remain completely intact under the reaction conditions. In addition to introducing a convenient procedure for preparing stereodefined spirocyclic systems, a new ring expansion sequence has been developed that appears extremely general for the preparation of various ring systems.
• Sequenced Reactions with Samarium(II) Iodide. Sequential Intermolecular Carbonyl Addition/Intramolecular Nucleophilic Acyl Substitution for the Preparation of Seven-, Eight-, and Nine-Membered Carbocycles
  作者：Gary A. Molander、Cristina Alonso-Alija

  DOI：10.1021/jo980119e

  日期：1998.6.1

  Samarium(II) iodide has been employed to promote a tandem intermolecular carbonyl addition/intramolecular nucleophilic acyl substitution sequence, generating seven- through nine-membered monocyclic, bicyclic, and tricyclic ring systems with good yields and high diastereoselectivities. This tandem reaction consists of an intermolecular reaction followed by an intramolecular ring expansion that results in a formal [m + n] cycloaddition, starting from extremely simple, readily available substrates. The regioselectivity and stereoselectivity of the process arise from a tuning of the reducing power of samarium(II) iodide with nickel(II) iodide in the first step and irradiation with visible light in the second. By using this method, a variety of structural motifs have been assembled rapidly in good yields.
• Absolute Sense of Twist of the C12C13 Bond of the Retinal Chromophore in Bovine Rhodopsin Based on Exciton-Coupled CD Spectra of 11,12-Dihydroretinal Analogues
  作者：Qiang Tan、Jihong Lou、Babak Borhan、Elena Karnaukhova、Nina Berova、Koji Nakanishi

  DOI：10.1002/anie.199720891

  日期：1997.10.17