1-Methoxy-1-[(1R)-naphth-2-ylethoxy]propan-2-one | 264224-31-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Methoxy-1-[(1R)-naphth-2-ylethoxy]propan-2-one
• 英文别名: 1-methoxy-1-((R)-1-(naphthalen-2-yl)ethoxy)propan-2-one；1-methoxy-1-[(1R)-1-naphthalen-2-ylethoxy]propan-2-one
• CAS: 264224-31-9
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: IUUBTFGJMNAIJR-ZGTOLYCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  1-Methoxy-1-[(1R)-naphth-2-ylethoxy]propan-2-one 在 三氟甲磺酸三甲基硅酯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.08h， 生成 benzenecarbothioic acid S-[2-{(1R)-naphth-2-yl-ethoxy}-3-oxo-8-oxabicyclo[3.2.1]oct-6-en-7-yl] ester
  参考文献：
  名称：

  High Regio-, Chemo-, and Stereoselectivity via Low-Temperature 4 + 3 Cycloadditions. Convergent Synthesis of Multifunctionalized Vinylmetals (M = Si, Sn) and S-Vinyl Benzenecarbothioates

  摘要：

  [GRAPHICS]A series of enantiomerically pure 8-oxabicyclo[3.2.1]oct-6-en-3-ones functionalized in the unsaturated two-carbon bridge has been prepared by the title reaction. Carbocation reactivity has been fined-tuned at -95 degrees C and adjusted to diene nucleophilicity. Conventional electrophilic substitution of 3-silylated and 3-stannylated furan is suppressed in favor of the rapid 4 + 3 cycloaddition mode. In the case of cycloadduct 13A, stereoselectivity (17:1) is perfectly matched to regioselectivity (17:1). High stereoselection as well as unprecedented regioselection and chemoselection is attributed to the low-temperature cycloaddition protocol and the design of chiral auxiliary and tether.

  DOI：

  10.1021/ol991386p
• 作为产物：
  描述：

  1-溴-1-甲氧基-丙-2-酮 、 (R)-(+)-1-(2-萘基)乙醇 在 正丁基锂 作用下， 以 乙醚 为溶剂， 生成 1-Methoxy-1-[(1R)-naphth-2-ylethoxy]propan-2-one
  参考文献：
  名称：

  High Regio-, Chemo-, and Stereoselectivity via Low-Temperature 4 + 3 Cycloadditions. Convergent Synthesis of Multifunctionalized Vinylmetals (M = Si, Sn) and S-Vinyl Benzenecarbothioates

  摘要：

  [GRAPHICS]A series of enantiomerically pure 8-oxabicyclo[3.2.1]oct-6-en-3-ones functionalized in the unsaturated two-carbon bridge has been prepared by the title reaction. Carbocation reactivity has been fined-tuned at -95 degrees C and adjusted to diene nucleophilicity. Conventional electrophilic substitution of 3-silylated and 3-stannylated furan is suppressed in favor of the rapid 4 + 3 cycloaddition mode. In the case of cycloadduct 13A, stereoselectivity (17:1) is perfectly matched to regioselectivity (17:1). High stereoselection as well as unprecedented regioselection and chemoselection is attributed to the low-temperature cycloaddition protocol and the design of chiral auxiliary and tether.

  DOI：

  10.1021/ol991386p

文献信息

• Studies towards the Synthesis of (+)‐Dictyoxetane
  作者：Joseph Benford‐Ward、Sanaz Ahmadipour、Aliya Sembayeva、Louise Male、Richard S. Grainger

  DOI：10.1002/chem.202202429

  日期：2022.12.20

  Hajos-Parrish ketone is used to prepare a key building block for the total synthesis of the marine natural product dictyoxetane in enantiopure form. A synthetic alternative to the Garst-Spencer furan annelation is developed, and the reactivity and diastereoselectivity of the resulting tetrasubstituted chiral furan in cycloaddition reactions towards an appropriately functionalised carbocyclic core of dictyoxetane

  Hajos-Parrish 酮用于制备对映体纯形式的海洋天然产物双氧环乙烷全合成的关键构件。开发了 Garst-Spencer 呋喃环化的合成替代品，并探索了所得四取代手性呋喃在环加成反应中对双氧杂环丁烷的适当官能化碳环核的反应性和非对映选择性。
• Stark, Christian B. W.; Pierau, Sabine; Wartchow, Rudolf, Chemistry - A European Journal, 2000, vol. 6, # 4, p. 684 - 691
  作者：Stark, Christian B. W.、Pierau, Sabine、Wartchow, Rudolf、Hoffmann

  DOI：——

  日期：——
• High Regio-, Chemo-, and Stereoselectivity via Low-Temperature 4 + 3 Cycloadditions. Convergent Synthesis of Multifunctionalized Vinylmetals (M = Si, Sn) and <i>S</i>-Vinyl Benzenecarbothioates
  作者：Hartmut Beck、Christian B. W. Stark、H. Martin R. Hoffmann

  DOI：10.1021/ol991386p

  日期：2000.4.1

  [GRAPHICS]A series of enantiomerically pure 8-oxabicyclo[3.2.1]oct-6-en-3-ones functionalized in the unsaturated two-carbon bridge has been prepared by the title reaction. Carbocation reactivity has been fined-tuned at -95 degrees C and adjusted to diene nucleophilicity. Conventional electrophilic substitution of 3-silylated and 3-stannylated furan is suppressed in favor of the rapid 4 + 3 cycloaddition mode. In the case of cycloadduct 13A, stereoselectivity (17:1) is perfectly matched to regioselectivity (17:1). High stereoselection as well as unprecedented regioselection and chemoselection is attributed to the low-temperature cycloaddition protocol and the design of chiral auxiliary and tether.