[9-[2-(Hydroxymethyl)phenyl]-2,2-dioxo-1,3-dihydrobenzo[f][2]benzothiol-5-yl]methanol | 1421759-76-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: [9-[2-(Hydroxymethyl)phenyl]-2,2-dioxo-1,3-dihydrobenzo[f][2]benzothiol-5-yl]methanol
• 英文别名: [9-[2-(hydroxymethyl)phenyl]-2,2-dioxo-1,3-dihydrobenzo[f][2]benzothiol-5-yl]methanol
• CAS: 1421759-76-3
• 化学式: C₂₀H₁₈O₄S
• 分子量: 354.427
• InChiKey: IZSWHMNPWYTGIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  83
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [9-[2-(Hydroxymethyl)phenyl]-2,2-dioxo-1,3-dihydrobenzo[f][2]benzothiol-5-yl]methanol 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 8-(azidomethyl)-4-(2-(azidomethyl)phenyl)-1,3-dihydronaphtho[2,3-c]thiophene 2,2-dioxide
  参考文献：
  名称：

  Asymmetric Garratt–Braverman Cyclization: A Route to Axially Chiral Aryl Naphthalene–Amino Acid Hybrids

  摘要：

  We report the first example of a highly diastereoselective Garratt-Braverman cyclization leading to the synthesis of chiral aryl naphthalene amino acid hybrids in excellent yields. The stereogenecity in the amino acid has induced high diastereoselectivity for the reaction. Computations based on density functional theory indicated a lower activation free energy barrier for the M isomer as compared to that for the P diastereomer (Delta G = 3.48 kcal/mol). Comparison of the recorded CD spectrum of the product with the calculated one also supported the preferential formation of the M diastereomer.

  DOI：

  10.1021/jo500771g
• 作为产物：
  描述：

  Methyl 2-[3-[3-(2-methoxycarbonylphenyl)prop-2-ynylsulfanyl]prop-1-ynyl]benzoate 在 sodium tetrahydroborate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 6.0h， 生成 [9-[2-(Hydroxymethyl)phenyl]-2,2-dioxo-1,3-dihydrobenzo[f][2]benzothiol-5-yl]methanol
  参考文献：
  名称：

  Asymmetric Garratt–Braverman Cyclization: A Route to Axially Chiral Aryl Naphthalene–Amino Acid Hybrids

  摘要：

  We report the first example of a highly diastereoselective Garratt-Braverman cyclization leading to the synthesis of chiral aryl naphthalene amino acid hybrids in excellent yields. The stereogenecity in the amino acid has induced high diastereoselectivity for the reaction. Computations based on density functional theory indicated a lower activation free energy barrier for the M isomer as compared to that for the P diastereomer (Delta G = 3.48 kcal/mol). Comparison of the recorded CD spectrum of the product with the calculated one also supported the preferential formation of the M diastereomer.

  DOI：

  10.1021/jo500771g

文献信息

• A chemo-enzymatic route to differentially protected aryl-naphthalenes
  作者：Arpita Panja、Deboki Ghosh、Amit Basak

  DOI：10.1016/j.bmcl.2012.11.010

  日期：2013.2

  more exposed acetoxymethyl or hydroxy methyl attached to the naphthalene ring binds to the active site of the enzyme and underwent hydrolysis/acetylation. The method provides easy access to differentially protected aryl-naphthalenes which should allow further modifications.

  由双炔丙基砜，醚和胺经Garratt-Braverman环化反应制得的芳基萘二乙酸酯已通过AK脂肪酶选择性地水解成单乙酸酯12a - c。区域异构的单乙酸酯13a-c是使用相同的酶通过将相应的二醇乙酰化而制得的。在这两种情况下，与萘环连接的暴露度更高的乙酰氧基甲基或羟甲基与酶的活性位点结合，并进行水解/乙酰化。该方法提供了容易获得差异保护的芳基-萘的途径，这应允许进一步的修饰。