2,8-dimethylnon-3-en-5-one | 850807-32-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,8-dimethylnon-3-en-5-one
• 英文别名: (E)-2,8-dimethylnon-3-en-5-one
• CAS: 850807-32-8
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: KDEJDAUELNCHHD-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  2,8-dimethylnon-3-en-5-one 在 三氟化硼乙醚 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Highly Substituted Tetrahydropyrones from Hetero-Diels−Alder Reactions of 2-Alkenals with Stereochemical Induction from Chiral Dienes

  摘要：

  A new method for the stereoselective synthesis of libraries of 2,3,5-trisubstituted tetrahydro-gamma-pyrones and the corresponding tetrahydropyran-4-ols is reported. Dienes with a chiral moiety at position 5 were synthesized starting from (triphenylphosphoranylidene)acetone. In hetero-Diels-Alder (HDA) reactions, especially with alpha,beta-unsaturated aldehydes, they induce diastereomeric ratios from 4:1 to 14:1. Through selective epimerization and reduction, further building blocks are available. These constitute ideal starting points for their use in the total synthesis of complex polyketide macrocycles, especially with the vinyl group available for metathetic coupling.

  DOI：

  10.1021/jo0488311
• 作为产物：
  描述：

  isoamylcarbonylmethylenetriphenyl phosphorane 、 异丁醛 以 二氯甲烷 为溶剂， 以36%的产率得到2,8-dimethylnon-3-en-5-one
  参考文献：
  名称：

  Highly Substituted Tetrahydropyrones from Hetero-Diels−Alder Reactions of 2-Alkenals with Stereochemical Induction from Chiral Dienes

  摘要：

  A new method for the stereoselective synthesis of libraries of 2,3,5-trisubstituted tetrahydro-gamma-pyrones and the corresponding tetrahydropyran-4-ols is reported. Dienes with a chiral moiety at position 5 were synthesized starting from (triphenylphosphoranylidene)acetone. In hetero-Diels-Alder (HDA) reactions, especially with alpha,beta-unsaturated aldehydes, they induce diastereomeric ratios from 4:1 to 14:1. Through selective epimerization and reduction, further building blocks are available. These constitute ideal starting points for their use in the total synthesis of complex polyketide macrocycles, especially with the vinyl group available for metathetic coupling.

  DOI：

  10.1021/jo0488311

文献信息

• Processes for preparing beta-hydroxy-ketones and alpha,beta-unsaturated ketones
  申请人：Barnicki Donald Scott

  公开号：US20050004401A1

  公开（公告）日：2005-01-06

  Processes for producing β-hydroxy-ketones and α,β-unsaturated ketones are disclosed which comprise the crossed condensation of an aldehyde with a ketone in the presence of a hydroxide or alkoxide of alkali metal or an alkaline earth metal as catalyst. The products of the process, β-hydroxy-ketones and α,β-unsaturated ketones, are useful for the preparation of many commercially important products in the chemical process industries including solvents, drug intermediates, flavors and fragrances, other specialty chemical intermediates.

  披露了生产β-羟基酮和α,β-不饱和酮的过程，这些过程包括在碱金属或碱土金属的氢氧化物或醇盐的催化下，醛与酮的交叉缩合。该过程的产品，即β-羟基酮和α,β-不饱和酮，对于化学工艺工业中许多商业上重要产品的制备非常有用，包括溶剂、药物中间体、香精和香料、以及其他专用化学品中间体。
• PROCESSES FOR PREPARING BETA-HYDROXY-KETONES AND ALPHA, BETA-UNSATURATED KETONES
  申请人：EASTMAN CHEMICAL COMPANY

  公开号：EP1638913A1

  公开（公告）日：2006-03-29
• US6960694B2
  申请人：——

  公开号：US6960694B2

  公开（公告）日：2005-11-01
• [EN] PROCESSES FOR PREPARING BETA-HYDROXY-KETONES AND ALPHA, BETA-UNSATURATED KETONES<br/>[FR] PROCEDES D'ELABORATION DE BETA-HYDROXY-CETONES ET DE CETONES ALPHA, BETA-INSATUREES
  申请人：EASTMAN CHEM CO

  公开号：WO2005005361A1

  公开（公告）日：2005-01-20

  Processes for producing β-hydroxy-ketones and a,β-­unsaturated ketones are disclosed which comprise the crossed condensation of an aldehyde with a ketone in the presence of a hydroxide or aikoxide of aikali metal or an aikaline earth metal as catalyst. The products of the process, β-hydroxy­ketones and a,β-unsaturated ketones, are useful for the preparation of many commercially important products in the chemical process industries including solvents, drug intermediates, flavors and fragrances, other specialty chemical intermediates.
• Highly Substituted Tetrahydropyrones from Hetero-Diels−Alder Reactions of 2-Alkenals with Stereochemical Induction from Chiral Dienes
  作者：Eelco Ruijter、Heike Schültingkemper、Ludger A. Wessjohann

  DOI：10.1021/jo0488311

  日期：2005.4.1

  A new method for the stereoselective synthesis of libraries of 2,3,5-trisubstituted tetrahydro-gamma-pyrones and the corresponding tetrahydropyran-4-ols is reported. Dienes with a chiral moiety at position 5 were synthesized starting from (triphenylphosphoranylidene)acetone. In hetero-Diels-Alder (HDA) reactions, especially with alpha,beta-unsaturated aldehydes, they induce diastereomeric ratios from 4:1 to 14:1. Through selective epimerization and reduction, further building blocks are available. These constitute ideal starting points for their use in the total synthesis of complex polyketide macrocycles, especially with the vinyl group available for metathetic coupling.