cis-4-Phenyl-5-isopropyldihydro-2(3H)-furanone

• 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: cis-4-Phenyl-5-isopropyldihydro-2(3H)-furanone
• 英文别名: dihydro-5-(1-methylethyl)-4-phenyl-2(3H)-furanone；(4R,5S)-4-phenyl-5-propan-2-yloxolan-2-one
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: AAIBSKFTRVFCAW-YPMHNXCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (3R,4S)-4-Methoxymethoxy-5-methyl-3-phenyl-hexanal 在 chromium(VI) oxide 、 硫酸 、 oxonium 作用下， 生成 cis-4-Phenyl-5-isopropyldihydro-2(3H)-furanone
  参考文献：
  名称：

  Highly selective acyclic homoaldol chemistry synthesis of -3,4-disubstituted butyrolactones

  摘要：

  DOI：

  10.1016/s0040-4039(00)80378-0

文献信息

• Silyl Phosphites. XVIII. Versatile Utility of α-(Trimethylsilyloxy)alkylphosphonates as Key Intermediates for Transformation of Aldehydes into Several Carbonyl Derivatives
  作者：Mitsuo Sekine、Masashi Nakajima、Akiko Kume、Akio Hashizume、Tsujiaki Hata

  DOI：10.1246/bcsj.55.224

  日期：1982.1

  trimethylsilyl phosphite (DTMSP) with aldehydes were converted, by treatment with lithium diisopropylamide (LDA) followed by the successive alkylation and alkaline hydrolysis, to carbonyl derivatives involving aldehydes, unsymmetrical ketones, β,γ-unsaturated ketones, and carboxylic acids. β-Substituted carboxylic esters and γ-substituted lactones were prepared by use of the carbonyl addition compounds of DTMSP

  通过用二异丙基氨基锂 (LDA) 处理，然后连续烷基化和碱水解，将二乙基三甲基甲硅烷基亚磷酸酯 (DTMSP) 与醛的羰基加成化合物转化为涉及醛、不对称酮、β,γ-不饱和酮和羧酸的羰基衍生物酸。利用DTMSP的羰基加成化合物与α,β-不饱和醛制备β-取代羧酸酯和γ-取代内酯。
• Expeditious access to<i>cis</i>-β-aryl, γ-alkyl disubstituted (±)-γ-butyrolactones<i>via</i>nickel-hydride catalysis
  作者：O. Stephen Ojo、Hannah J. Steel、Haralampos N. Miras

  DOI：10.1039/d3ob00895a

  日期：——

  NiCl2·6H2O and NaBH4 in MeOH for rapid access to cis-β,γ-disubstituted γ-butyrolactones is described. The reaction was selective for cis-products, which were obtained in good to excellent yields. This study showcased the influence of steric hindrance and angle strain on the diastereoselectivity outcome of conjugate reductions facilitated by in situ generated nickel-hydride.

  描述了使用MeOH中的5mol% NiCl 2 ·6H 2 O和NaBH 4对β-和γ-取代的丁烯内酯进行1,4-还原，以快速获得顺式-β,γ-二取代的γ-丁内酯。该反应对顺式产物具有选择性，其收率良好至优异。这项研究展示了空间位阻和角应变对原位生成的氢化镍促进的共轭还原的非对映选择性结果的影响。
• Mg-Promoted Reductive Cross-Coupling of Ethyl .beta.-Arylacrylates with Aldehydes
  作者：Toshinobu Ohno、Yoshio Ishino、Yoshihiro Tsumagari、Ikuzo Nishiguchi

  DOI：10.1021/jo00107a029

  日期：1995.1