(R)-2-hydroxy-4-(4-methoxyphenoxy)-2-methylbutyl 2,2,2-trimethylacetate | 237393-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-2-hydroxy-4-(4-methoxyphenoxy)-2-methylbutyl 2,2,2-trimethylacetate
• 英文别名: (R)-2-hydroxy-4-(4-methoxyphenoxy)-2-methylbutyl pivalate；[(2R)-2-hydroxy-4-(4-methoxyphenoxy)-2-methylbutyl] 2,2-dimethylpropanoate
• CAS: 237393-21-4
• 化学式: C₁₇H₂₆O₅
• 分子量: 310.39
• InChiKey: NCUZYGNZFGLWBD-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2-hydroxy-4-(4-methoxyphenoxy)-2-methylbutyl 2,2,2-trimethylacetate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 2,4,6-三氯苯甲酰氯 、 乙基溴化镁 、 potassium trimethylsilonate 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 三乙胺 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 177.5h， 生成 (2S,3R,5R)-5-methyl-2-(3-methylbut-3-enyl)-5-propyltetrahydrofuran-3-yl (2E,11E)-(4S,7R,9S,10R)-7,9-dihydroxy-4,7,10-trimethyl-6-oxo-12-phenyldodeca-2,11-dienoate
  参考文献：
  名称：

  Total Synthesis of Amphidinolide Y by Formation of Trisubstituted (E)-Double Bond via Ring-Closing Metathesis of Densely Functionalized Alkenes

  摘要：

  Amphidinolide Y, a 17-membered cytotoxic macrolide isolated from marine dinoflagellates, has been synthesized via ring-closing metathesis to assemble the congested trisubstituted (E)-double bond. The seco precursor was prepared from readily available chiral synthons with the tetrahydrofuran ring formed via 5-endo epoxide ring-opening cyclization. It was found that the C6-keto seco substrate showed higher reactivity toward Grubbs' second generation catalyst while Schrock's Mo catalyst was completely inactive for formation of the macrocycle.

  DOI：

  10.1021/ol0710360
• 作为产物：
  描述：

  3-甲基-3-丁烯-1-醇 在 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 AD-mix-β 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 11.0h， 生成 (R)-2-hydroxy-4-(4-methoxyphenoxy)-2-methylbutyl 2,2,2-trimethylacetate
  参考文献：
  名称：

  Total Synthesis of Amphidinolide Y by Formation of Trisubstituted (E)-Double Bond via Ring-Closing Metathesis of Densely Functionalized Alkenes

  摘要：

  Amphidinolide Y, a 17-membered cytotoxic macrolide isolated from marine dinoflagellates, has been synthesized via ring-closing metathesis to assemble the congested trisubstituted (E)-double bond. The seco precursor was prepared from readily available chiral synthons with the tetrahydrofuran ring formed via 5-endo epoxide ring-opening cyclization. It was found that the C6-keto seco substrate showed higher reactivity toward Grubbs' second generation catalyst while Schrock's Mo catalyst was completely inactive for formation of the macrocycle.

  DOI：

  10.1021/ol0710360

文献信息

• Total Syntheses of Amphidinolides B, G, and H
  作者：Akihiro Hara、Ryo Morimoto、Yuki Iwasaki、Tsuyoshi Saitoh、Yuichi Ishikawa、Shigeru Nishiyama

  DOI：10.1002/anie.201204992

  日期：2012.9.24

  Not one, not two, but three: Total syntheses of amphidinolides B, G, and H, which exhibit strong, nanogram‐scale cytotoxicity against various tumor cell lines, have been executed. The synthetic strategy relied on implementation of a diene construction protocol and a diastereoselective aldol process. The 26‐ and 27‐membered macrocyclic lactone rings were efficiently constructed by using ring‐closing

  不是一个，不是两个，而是三个：已执行了对两类肿瘤细胞系表现出强大的纳克级细胞毒性的两性霉素B，G和H的总合成。合成策略依赖于二烯构建方案和非对映选择性羟醛工艺的实施。使用闭环复分解（RCM）可有效构建26和27元大环内酯环。
• Total Synthesis of Amphidinolide Y by Formation of Trisubstituted (<i>E</i>)-Double Bond via Ring-Closing Metathesis of Densely Functionalized Alkenes
  作者：Jian Jin、Yile Chen、Yannian Li、Jinlong Wu、Wei-Min Dai

  DOI：10.1021/ol0710360

  日期：2007.6.1

  Amphidinolide Y, a 17-membered cytotoxic macrolide isolated from marine dinoflagellates, has been synthesized via ring-closing metathesis to assemble the congested trisubstituted (E)-double bond. The seco precursor was prepared from readily available chiral synthons with the tetrahydrofuran ring formed via 5-endo epoxide ring-opening cyclization. It was found that the C6-keto seco substrate showed higher reactivity toward Grubbs' second generation catalyst while Schrock's Mo catalyst was completely inactive for formation of the macrocycle.