trans-5-cyclohexyl-4-methyl-3-methylenedihydrofuran-2(3H)-one | 120094-44-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: trans-5-cyclohexyl-4-methyl-3-methylenedihydrofuran-2(3H)-one
• 英文别名: trans-5-cyclohexyl-4-methyl-3-methylene-dihydro-furan-2-one；(4R,5S)-5-cyclohexyl-4-methyl-3-methylideneoxolan-2-one
• CAS: 120094-44-2；120094-52-2；133285-92-4；133285-97-9
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: UUCNMGNRHOPXTA-LDYMZIIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环己烷基甲醛 、 methyl (Z)-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)but-2-enoate 在 ytterbium(III) triflate 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以90%的产率得到trans-5-cyclohexyl-4-methyl-3-methylenedihydrofuran-2(3H)-one
  参考文献：
  名称：

  Acidity-Directed Synthesis of Substituted γ-Butyrolactones from Aliphatic Aldehydes

  摘要：

  The strength of the Lewis or Bronsted acids controls the formation of either beta,gamma-disubstituted-alpha-methylene-gamma-butyrolactones or gamma-substituted-alpha-alkylidene-gamma-butyrolactones via the lactonization or oxonia cope rearrangement-lactonization, respectively, of the borate intermediates resulting from the crotylboration of aliphatic aldehydes with ester-containing crotylboronates, such as (E)-methyl 2-boramethyl-2-butenoates.

  DOI：

  10.1021/ol0705806

文献信息

• Palladium-catalyzed carbonyl allylation by 2-(hydroxymethyl)acrylate derivatives: synthesis of α-methylene-γ-butyrolactones
  作者：Yoshiro Masuyama、Yumiko Nimura、Yasuhiko Kurusu

  DOI：10.1016/0040-4039(91)80861-y

  日期：1991.1

  Ethyl 2-(Hydroxymethyl)acrylate derivatives serve as reagents for 2-ethoxycarbonylallylation of carbonyl compounds using PdCl2(PhCN)2-SnCl2 system to produce α-methylene-γ-butyrolactones diastereoselectivity.

  2-（羟甲基）丙烯酸乙酯衍生物用作使用PdCl 2（PhCN）2 -SnCl 2体系进行羰基化合物的2-乙氧基羰基化的试剂，以产生α-亚甲基-γ-丁内酯非对映选择性。
• Triflic Acid-Catalyzed Additions of 2-Alkoxycarbonyl Allylboronates to Aldehydes. Study of Scope and Mechanistic Investigation of the Reaction Stereochemistry
  作者：Tim G. Elford、Yuichiro Arimura、Siu Hong Yu、Dennis G. Hall

  DOI：10.1021/jo062151b

  日期：2007.2.1

  The substrate scope and the effect of substrate on the observed inversion of stereoselectivity in the triflic acid-catalyzed allylboration reaction between 2-alkoxycarbonyl allylboronates and aldehydes are presented. A mechanistic investigation is described so as to confirm the involvement of a carbocation intermediate as the source of stereochemical inversion. This methodology allows a facile access

  介绍了底物的范围和底物对在三氟乙酸催化的2-硼氧基羰基烯丙基硼酸酯和醛之间的三氟甲磺酸催化的烯丙基硼化反应中观察到的立体选择性转化的影响。描述了一种机理研究，以确认碳正离子中间体作为立体化学转化的来源。该方法允许容易地获得在α位具有外亚甲基的β，γ-二取代的五元环内酯。