(4R,5S)-4-环己基-5-苯基二氢呋喃-2(3H)-酮 | 299908-79-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: (4R,5S)-4-环己基-5-苯基二氢呋喃-2(3H)-酮
• 英文名称: (4R,5S)-4-cyclohexyl-5-phenyl-butyrolactone
• 英文别名: (4R,5S)-4-Cyclohexyl-5-phenyldihydrofuran-2(3H)-one；(4R,5S)-4-cyclohexyl-5-phenyloxolan-2-one
• CAS: 299908-79-5
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: SKVJYZIWMIXDDX-GDBMZVCRSA-N

物化性质

• 沸点：
  410.3±34.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1-(1-萘基)乙胺 、 (4R,5S)-4-环己基-5-苯基二氢呋喃-2(3H)-酮 在 三甲基铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 48.5h， 以41%的产率得到(3R,4S,1'S)-3-cyclohexyl-4-hydroxy-N-(1-naphthalen-1-yl-ethyl)-4-phenylbutyramide
  参考文献：
  名称：

  Highly Enantioselective Syntheses of anti Homoaldol Products by (−)-Sparteine-Mediated Lithiation/Transmetalation/Substitution of N-Boc Allylic Amines

  摘要：

  [GRAPHICS](-)-Sparteine-mediated lithiation/transmetalation/substitution of N-Boc allylic amines provides anti-configured homoaldol precursors in yields of 38-85% and enantiomeric ratios of 83:17-99:1. Subsequent O-protection and hydrolysis allows access to O-protected homoaldol adducts in good yields. The absolute configurations of the homoaldol products have been assigned by calculation of optical rotations and by X-ray crystallography of derivatives. A stereochemical course of reaction for the lithiation/transmetalation/substitution sequence is proposed.

  DOI：

  10.1021/ol006186o
• 作为产物：
  描述：

  (3S,4S)-N-(t-butoxycarbonyl)-N-(4-methoxyphenyl)-3-cyclohexyl-4-hydroxy-4-phenyl-1-butene-1-amine 在 甲烷磺酸 、 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (4R,5S)-4-环己基-5-苯基二氢呋喃-2(3H)-酮
  参考文献：
  名称：

  Highly Enantioselective Syntheses of anti Homoaldol Products by (−)-Sparteine-Mediated Lithiation/Transmetalation/Substitution of N-Boc Allylic Amines

  摘要：

  [GRAPHICS](-)-Sparteine-mediated lithiation/transmetalation/substitution of N-Boc allylic amines provides anti-configured homoaldol precursors in yields of 38-85% and enantiomeric ratios of 83:17-99:1. Subsequent O-protection and hydrolysis allows access to O-protected homoaldol adducts in good yields. The absolute configurations of the homoaldol products have been assigned by calculation of optical rotations and by X-ray crystallography of derivatives. A stereochemical course of reaction for the lithiation/transmetalation/substitution sequence is proposed.

  DOI：

  10.1021/ol006186o