N-[5-[(1R,2R)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylpropyl]-3,6-dioxocyclohexa-1,4-dien-1-yl]acetamide | 1421341-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[5-[(1R,2R)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylpropyl]-3,6-dioxocyclohexa-1,4-dien-1-yl]acetamide
• CAS: 1421341-72-1
• 化学式: C₂₄H₄₃NO₅Si₂
• 分子量: 481.78
• InChiKey: JSKHKUSUUHBFKS-OPAMFIHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[5-[(1R,2R)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylpropyl]-3,6-dioxocyclohexa-1,4-dien-1-yl]acetamide 在 sodium dithionite 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以99%的产率得到N-[3-[(1R,2R)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylpropyl]-2,5-dihydroxyphenyl]acetamide
  参考文献：
  名称：

  Toward a Total Synthesis of Divergolide A; Synthesis of the Amido Hydro- quinone Core and the C10–C15 Fragment

  摘要：

  A ring-closing metathesis (RCM) approach was envisioned for installing the E double bond at the C9 and C10 positions of divergolide A, isolated from a mangrove endophyte. Accordingly, the C10-C15 diene diol fragment and the amido hydroquinone core with the requisite functionalities and stereochemistry have been synthesized by using the norephedrine-based syn-selective glycolate aldol and the anti-selective aldol reactions, respectively. CuI-catalyzed amidation was employed to access the anilide intermediate, which was further transformed into the amido hydroquinone core.

  DOI：

  10.1055/s-0032-1317491
• 作为产物：
  描述：

  N-[3-[(1R,2R)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylpropyl]-5-[(4-methoxyphenyl)methoxy]phenyl]acetamide 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 水 、 乙腈 为溶剂， 反应 0.02h， 生成 N-[5-[(1R,2R)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylpropyl]-3,6-dioxocyclohexa-1,4-dien-1-yl]acetamide
  参考文献：
  名称：

  Toward a Total Synthesis of Divergolide A; Synthesis of the Amido Hydro- quinone Core and the C10–C15 Fragment

  摘要：

  A ring-closing metathesis (RCM) approach was envisioned for installing the E double bond at the C9 and C10 positions of divergolide A, isolated from a mangrove endophyte. Accordingly, the C10-C15 diene diol fragment and the amido hydroquinone core with the requisite functionalities and stereochemistry have been synthesized by using the norephedrine-based syn-selective glycolate aldol and the anti-selective aldol reactions, respectively. CuI-catalyzed amidation was employed to access the anilide intermediate, which was further transformed into the amido hydroquinone core.

  DOI：

  10.1055/s-0032-1317491

文献信息

• Toward a Total Synthesis of Divergolide A; Synthesis of the Amido Hydro- quinone Core and the C10–C15 Fragment
  作者：Wei-Min Dai、Guanglian Zhao、Jinlong Wu

  DOI：10.1055/s-0032-1317491

  日期：——

  A ring-closing metathesis (RCM) approach was envisioned for installing the E double bond at the C9 and C10 positions of divergolide A, isolated from a mangrove endophyte. Accordingly, the C10-C15 diene diol fragment and the amido hydroquinone core with the requisite functionalities and stereochemistry have been synthesized by using the norephedrine-based syn-selective glycolate aldol and the anti-selective aldol reactions, respectively. CuI-catalyzed amidation was employed to access the anilide intermediate, which was further transformed into the amido hydroquinone core.