Tert-butyl 3-[1,4-dioxo-3-(phenylmethoxymethyl)naphthalen-2-yl]-3-hydroxypropanoate | 364729-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Tert-butyl 3-[1,4-dioxo-3-(phenylmethoxymethyl)naphthalen-2-yl]-3-hydroxypropanoate
• CAS: 364729-03-3
• 化学式: C₂₅H₂₆O₆
• 分子量: 422.478
• InChiKey: DTVWPKKSJIJLEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Tert-butyl 3-[1,4-dioxo-3-(phenylmethoxymethyl)naphthalen-2-yl]-3-hydroxypropanoate 在 四氧化锇 、 N-甲基吗啉氧化物 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 18.0h， 生成 (2S,3R,4'R)-2,4'-dihydroxy-2-(phenylmethoxymethyl)spiro[naphthalene-3,5'-oxolane]-1,2',4-trione
  参考文献：
  名称：

  Concise Synthesis of a Lactonamycin Model System by Diastereoselective Dihydroxylation of a Highly Functionalized Naphthoquinone

  摘要：

  [GRAPHICS]In this Letter, we describe an approach to the highly functionalized tetracycle 6, a model compound corresponding to the CDEF ring system contained in the recently discovered antibiotic lactonamycin. Our approach features an unprecedented, highly stereoselective dihydroxylation of quinone 13a, which leads directly to spirocyclic lactone 15, following acid-promoted deprotection/cyclization. The methodology described herein paves the way for a concise, highly diastereo- and enantioselective synthesis of the natural product.

  DOI：

  10.1021/ol016361g
• 作为产物：
  描述：

  2-bromo-3-(bromomethyl)-1,4-dimethoxynaphthalene 在 正丁基锂 、 ammonium cerium(IV) nitrate 、 sodium hydride 、 二异丙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 10.93h， 生成 Tert-butyl 3-[1,4-dioxo-3-(phenylmethoxymethyl)naphthalen-2-yl]-3-hydroxypropanoate
  参考文献：
  名称：

  Concise Synthesis of a Lactonamycin Model System by Diastereoselective Dihydroxylation of a Highly Functionalized Naphthoquinone

  摘要：

  [GRAPHICS]In this Letter, we describe an approach to the highly functionalized tetracycle 6, a model compound corresponding to the CDEF ring system contained in the recently discovered antibiotic lactonamycin. Our approach features an unprecedented, highly stereoselective dihydroxylation of quinone 13a, which leads directly to spirocyclic lactone 15, following acid-promoted deprotection/cyclization. The methodology described herein paves the way for a concise, highly diastereo- and enantioselective synthesis of the natural product.

  DOI：

  10.1021/ol016361g

文献信息

• Concise Synthesis of a Lactonamycin Model System by Diastereoselective Dihydroxylation of a Highly Functionalized Naphthoquinone
  作者：Christopher Cox、Samuel J. Danishefsky

  DOI：10.1021/ol016361g

  日期：2001.9.1

  [GRAPHICS]In this Letter, we describe an approach to the highly functionalized tetracycle 6, a model compound corresponding to the CDEF ring system contained in the recently discovered antibiotic lactonamycin. Our approach features an unprecedented, highly stereoselective dihydroxylation of quinone 13a, which leads directly to spirocyclic lactone 15, following acid-promoted deprotection/cyclization. The methodology described herein paves the way for a concise, highly diastereo- and enantioselective synthesis of the natural product.