(R)-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl] 2-(2-iodophenoxy)propanoate | 1383468-49-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl] 2-(2-iodophenoxy)propanoate
• CAS: 1383468-49-2
• 化学式: C₁₉H₂₇IO₃
• 分子量: 430.326
• InChiKey: OIYZYOXASORUBI-ZXFNITATSA-N

物化性质

• 沸点：
  443.9±25.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-碘苯酚 、 乳酸孟酯 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到(R)-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl] 2-(2-iodophenoxy)propanoate
  参考文献：
  名称：

  Chiral Aryl Iodide-Catalyzed Enantioselective α-Oxidation of Ketones

  摘要：

  Several chiral aryl iodides were synthesized and assessed as catalysts in the enantioselective alpha-oxytosylation of propiophenone and the oxidative cyclization of 5-oxo-5-phenylpentanoic acid to 5-benzoyldihydrofuran-2(3H)-one. The highest enantioselectivities obtained were 18 and 51% ee, respectively. The latter is the highest selectivity recorded to date for this reaction.

  DOI：

  10.1055/s-0031-1290590
• 作为试剂：
  描述：

  对甲苯磺酸 、 苯丙酮 在 (R)-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl] 2-(2-iodophenoxy)propanoate 、 间氯过氧苯甲酸 作用下， 以 乙腈 为溶剂， 生成 (R)-1-oxo-1-phenylpropan-2-yl 4-methylbenzenesulfonate 、 (2S)-2-[(4-methylbenzenesulfonyl)oxy]-1-phenylpropan-1-one
  参考文献：
  名称：

  Chiral Aryl Iodide-Catalyzed Enantioselective α-Oxidation of Ketones

  摘要：

  Several chiral aryl iodides were synthesized and assessed as catalysts in the enantioselective alpha-oxytosylation of propiophenone and the oxidative cyclization of 5-oxo-5-phenylpentanoic acid to 5-benzoyldihydrofuran-2(3H)-one. The highest enantioselectivities obtained were 18 and 51% ee, respectively. The latter is the highest selectivity recorded to date for this reaction.

  DOI：

  10.1055/s-0031-1290590

文献信息

• Metal-Free Enantioselective Oxidative Arylation of Alkenes: Hypervalent-Iodine-Promoted Oxidative C−C Bond Formation
  作者：Mio Shimogaki、Morifumi Fujita、Takashi Sugimura

  DOI：10.1002/anie.201609110

  日期：2016.12.19

  The enantioselective oxyarylation of (E)‐6‐aryl‐1‐silyloxylhex‐3‐ene was achieved using a lactate‐based chiral hypervalent iodine(III) reagent in the presence of boron trifluoride diethyl etherate. The silyl ether promotes the oxidative cyclization, and enhances the enantioselectivity. In addition, the corresponding aminoarylation was achieved.

  （E）-6-芳基-1-甲硅烷基氧合己烯-3-烯的对映选择性氧化芳基是在三氟化硼二乙基醚化物存在下使用基于乳酸酯的手性高价碘（III）试剂实现的。甲硅烷基醚促进氧化环化，并增强对映选择性。另外，实现了相应的氨基芳基化。