(-)-(6,6-dimethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester | 489429-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (-)-(6,6-dimethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester
• 英文别名: methyl 2-[(2R)-6,6-dimethyloxan-2-yl]acetate
• CAS: 489429-41-6
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: DUAKGXNZXHKACY-MRVPVSSYSA-N

物化性质

• 沸点：
  227.7±13.0 °C(Predicted)
• 密度：
  0.962±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(6,6-dimethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 21.0h， 以100%的产率得到(-)-(6,6-dimethyl-tetrahydro-pyran-2-yl)-acetic acid
  参考文献：
  名称：

  CeCl₃·7H₂O−NaI Catalyzed Hydrooxacyclization of Unsaturated 3-Hydroxy Esters

  摘要：

  [GRAPHICS]Cerium(III) chloride heptahydrate and sodium iodide in boiling acetonitrile promote cyclization of 3-hydroxyalkenoic acids esters giving 5-substituted tetrahydrofuranacetic acid esters and 6-substituted tetrahydropyranacetic acid esters in fair to good yield and with complete retention of the absolute configuration of the starting 3-hydroxy ester.

  DOI：

  10.1021/ol026955z
• 作为产物：
  描述：

  1-氯-3-甲基-2-丁烯 在 氢氧化钾 、 cerium(III) chloride 、 sodium iodide 作用下， 以 乙醚 、 乙醇 、 水 、 乙腈 为溶剂， 反应 95.0h， 生成 (-)-(6,6-dimethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester
  参考文献：
  名称：

  CeCl₃·7H₂O−NaI Catalyzed Hydrooxacyclization of Unsaturated 3-Hydroxy Esters

  摘要：

  [GRAPHICS]Cerium(III) chloride heptahydrate and sodium iodide in boiling acetonitrile promote cyclization of 3-hydroxyalkenoic acids esters giving 5-substituted tetrahydrofuranacetic acid esters and 6-substituted tetrahydropyranacetic acid esters in fair to good yield and with complete retention of the absolute configuration of the starting 3-hydroxy ester.

  DOI：

  10.1021/ol026955z

文献信息

• Enantioselective “clip-cycle” synthesis of di-, tri- and spiro-substituted tetrahydropyrans
  作者：Khadra Alomari、N. Sai Pavan Chakravarthy、Bastien Duchadeau、Kristaps Ermanis、Paul A. Clarke

  DOI：10.1039/d2ob00023g

  日期：——

  ω-Unsaturated alcohols were “clipped” via alkene metathesis to a thioester activating group, which was followed by a chiral phosphoric acid catalyzed intramolecular oxa-Michael cyclization to yield tetrahydropyrans and spiro-tetrahydropyrans with excellent enantioselectivity. The mechanism and origin of the enantioselectivity was probed by DFT calculations and kinetic isotope studies, where there was

  ω-不饱和醇通过烯烃复分解被“剪裁”成硫酯活化基团，随后手性磷酸催化分子内氧杂-迈克尔环化产生具有优异对映选择性的四氢吡喃和螺-四氢吡喃。通过 DFT 计算和动力学同位素研究探讨了对映选择性的机制和起源，其中计算和合成研究之间存在极好的相关性。
• CeCl₃·7H₂O−NaI Catalyzed Hydrooxacyclization of Unsaturated 3-Hydroxy Esters
  作者：Emanuela Marotta、Elisabetta Foresti、Tommaso Marcelli、Francesca Peri、Paolo Righi、Noemi Scardovi、Goffredo Rosini

  DOI：10.1021/ol026955z

  日期：2002.12.1

  [GRAPHICS]Cerium(III) chloride heptahydrate and sodium iodide in boiling acetonitrile promote cyclization of 3-hydroxyalkenoic acids esters giving 5-substituted tetrahydrofuranacetic acid esters and 6-substituted tetrahydropyranacetic acid esters in fair to good yield and with complete retention of the absolute configuration of the starting 3-hydroxy ester.