2-(3-bromo-1,4-dimethoxy-2-naphthylmethyl)-1,3-dioxolane | 161363-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(3-bromo-1,4-dimethoxy-2-naphthylmethyl)-1,3-dioxolane
• 英文别名: 2-[(3-Bromo-1,4-dimethoxynaphthalen-2-yl)methyl]-1,3-dioxolane
• CAS: 161363-74-2
• 化学式: C₁₆H₁₇BrO₄
• 分子量: 353.213
• InChiKey: MDXKEDUVAFGQEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-bromo-1,4-dimethoxy-2-naphthylmethyl)-1,3-dioxolane 在 正丁基锂 、 sodium hydride 作用下， 以 苯 为溶剂， 生成 5',10'-Dimethoxyspiro[2-benzofuran-3,1'-benzo[g]isochromene]-1-one
  参考文献：
  名称：

  The Synthesis of Radermachol

  摘要：

  Five different approaches to the preparation of 6,7-benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-1,5-dioxosuberane (3), an intermediate needed for the synthesis of radermachol (1), the red pigment from the roots of Radermachera xylocarpa, are described. The synthesis of radermachol (1) has been accomplished from 1,4-nephthoquinone in 14 steps.

  DOI：

  10.1021/jo00105a046
• 作为产物：
  描述：

  3-bromo-1,4-dimethoxy-2-naphthaleneacetonitrile 在 二异丁基氢化铝 、 对甲苯磺酸 作用下， 生成 2-(3-bromo-1,4-dimethoxy-2-naphthylmethyl)-1,3-dioxolane
  参考文献：
  名称：

  The Synthesis of Radermachol

  摘要：

  Five different approaches to the preparation of 6,7-benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-1,5-dioxosuberane (3), an intermediate needed for the synthesis of radermachol (1), the red pigment from the roots of Radermachera xylocarpa, are described. The synthesis of radermachol (1) has been accomplished from 1,4-nephthoquinone in 14 steps.

  DOI：

  10.1021/jo00105a046

文献信息

• Total Synthesis of Two Naphthoquinone Antibiotics, Psychorubrin and Pentalongin, and Their C(1)-Substituted Alkyl and Aryl Derivatives
  作者：Bart Kesteleyn、Norbert De Kimpe、Luc Van Puyvelde

  DOI：10.1021/jo9811975

  日期：1999.2.1

  The synthesis of 1-alkyl- and 1-aryl-1H-naphtho[2,3-c]pyran-5,10-dione bearing a C(3)-C(4) double bond, was performed by two alternative cyclization strategies of 2,3-disubstituted 1,4-naphthoquinones. Lemieux-Johnson oxidation of 2-allyl-3-hydroxymethyl-1,4-dimethoxynaphthalenes and subsequent oxidative demethylation of the intermediate 3,4-dihydro-5,10-dimethoxy-1H-naphtho[2,3 -c]pyran-3-oles to the corresponding 3,4-dihydro-3-hydroxy-1H-naphtho[2,3-c]pyran-5, 10-diones gave, after acid-catalyzed dehydration, the de shed 1H-naphtho[2,3-c]pyran-5,10-diones. Alternatively, the pyranonaphthoquinone ring system was constructed by intramolecular acid-catalyzed condensation of(3-hydroxymethyl-1,4-naphthoquinone-2-yl)acetaldehyde acetals. Using this synthetic approach, the synthesis of two naturally occurring naphthoquinone antibiotics, pentalongin and psychorubrin, is reported.
• The Synthesis of Radermachol
  作者：Balawant S. Joshi、Quingping Jiang、Taikyun Rho、S. William Pelletier

  DOI：10.1021/jo00105a046

  日期：1994.12

  Five different approaches to the preparation of 6,7-benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-1,5-dioxosuberane (3), an intermediate needed for the synthesis of radermachol (1), the red pigment from the roots of Radermachera xylocarpa, are described. The synthesis of radermachol (1) has been accomplished from 1,4-nephthoquinone in 14 steps.