4-methyl-hept-6-en-2-one | 35194-34-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methyl-hept-6-en-2-one
• 英文别名: 6-Hepten-2-one, 4-methyl-；4-methylhept-6-en-2-one
• CAS: 35194-34-4
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: GLVMKHSOGXAZCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methyl-hept-6-en-2-one 在 氢溴酸 作用下， 以 正戊烷 为溶剂， 生成 7-溴-4-甲基庚烷-2-酮
  参考文献：
  名称：

  Synthesis of .omega.-bromo ketones

  摘要：

  DOI：

  10.1021/jo00430a009
• 作为产物：
  描述：

  4-Methyl-1,5-heptadien-4-ol 以 正戊烷 为溶剂， 生成 4-methyl-hept-6-en-2-one
  参考文献：
  名称：

  Synthesis of .omega.-bromo ketones

  摘要：

  DOI：

  10.1021/jo00430a009

文献信息

• Chemistry of carbanions. 31. Cyclization of the metal enolates from .omega.-bromo ketones
  作者：Herbert O. House、William V. Phillips、Trevor S. B. Sayer、Cheuk-Chung Yau

  DOI：10.1021/jo00398a041

  日期：1978.2
• Stereochemical Investigations of Samarium(II) Iodide-Promoted 5-Exo and 6-Exo Ketyl-Olefin Radical Cyclization Reactions
  作者：Gary A. Molander、Jeffrey A. McKie

  DOI：10.1021/jo00109a018

  日期：1995.2

  Samarium(II) iodide (SmI2)-promoted ketyl cyclizations of several substituted, unsaturated ketones, providing various cyclopentyl and cyclohexyl systems, have been investigated. The resulting experiments provide stereochemical insight into these reactions and in addition outline the synthetic potential of these 5-exe and 6-exo radical cyclization processes.
• Electroorganic chemistry. 31. Reductive cyclization of nonconjugated olefinic ketones to cyclic tertiary alcohols
  作者：Tatsuya Shono、Ikuzo Nishiguchi、Hiroshi Ohmizu、Michiharu Mitani

  DOI：10.1021/ja00470a031

  日期：1978.1
• CHAMBERLIN, A. RICHARD;BLOOM, STEVEN H.;CERVINI, LAURA A.;FOTSCH, CHRISTO+, J. AMER. CHEM. SOC., 110,(1988) N 14, C. 4788-4796
  作者：CHAMBERLIN, A. RICHARD、BLOOM, STEVEN H.、CERVINI, LAURA A.、FOTSCH, CHRISTO+

  DOI：——

  日期：——
• Use of Hine's D Values To Predict the Position of the Equilibrium in the Cope Rearrangement of Multiply Substituted 1,5-Dienes
  作者：James P. Hagen、Kemberly D. Lewis、Scott W. Lovell、Paolo Rossi、Ayse Z. Tezcan

  DOI：10.1021/jo00128a019

  日期：1995.11

  A series of 1,5-dienes (1a-f) were employed to test whether Hine's D values can predict the position of equilibrium in Cope rearrangements. In the cases of the substituent pairs [OCH3, H], [OCH3, CH3], [N(CH3)(2), H], [N(CH3)(2), CH3], and [N(CH3)(2), OCH3], equilibrium constants calculated with Hine's D values gave reasonable agreement with those obtained experimentally. Dienes 1g-i were prepared to test whether reduction of the pi-donating character of a nitrogen substituent (carbamoyl vs dimethylamino) would change the directing ability of the nitrogen group. The aggregate order of directing ability was N(CH3)(2) > OCH3 > EtO(2)CN(CH3) > CH3 > A. Diene 15a, with a more complicated substitution pattern (OCH3 and CH3 versus CH3 and H) not directly amenable to analysis with D values, can be considered to reduce to the case of [OCH3, H]. The experimental K-eq obtained agreed with that expected for the [OCH3, H] pair. Dienes 15c and 16b, designed to test the pairs [CH3, SPh] and [OCH3, SPh], respectively, decomposed under the gas phase conditions of the rearrangement. Attempts to effect rearrangement with Pd(II) catalysis failed.