5-iodo-6-methoxy-3,4-tetrahydronaphthalen-1(2H)-one | 436091-93-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5-iodo-6-methoxy-3,4-tetrahydronaphthalen-1(2H)-one
• 英文别名: 5-iodo-6-methoxytetralone；5-Iodo-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one；5-iodo-6-methoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 436091-93-9
• 化学式: C₁₁H₁₁IO₂
• 分子量: 302.112
• InChiKey: ADSKUECQOUAYQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙烯基三乙氧基硅烷 、 5-iodo-6-methoxy-3,4-tetrahydronaphthalen-1(2H)-one 在 rhodium(III) chloride hydrate 、 sodium formate 、 三(4-三氟甲苯基)膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以89%的产率得到3,4-dihydro-5-iodo-6-methoxy-8-[2-(triethoxysilyl)ethyl]naphtalenone
  参考文献：
  名称：

  Ruthenium Chloride as an Efficient Catalytic Precursor for Hydroarylation Reactions via C−H bond Activation

  摘要：

  A very simple and efficient catalytic system for the hydroarylation of olefins by aromatic ketones and Michael acceptors using simple and inexpensive ruthenium trichloride as a ruthenium source is described. These very mild conditions (dioxane at 80 C) appeared to be highly compatible, tolerant, and selective toward various functional groups, and the ease of the protocol is highly convenient for synthetic purposes.

  DOI：

  10.1021/ol101038c
• 作为产物：
  描述：

  6-甲氧基-1-萘满酮 在 碘 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 7-iodo-6-methoxy-3,4-tetrahydronaphthalen-1(2H)-one 、 5-iodo-6-methoxy-3,4-tetrahydronaphthalen-1(2H)-one
  参考文献：
  名称：

  SelectfluorTM F-TEDA-BF4 mediated and solvent directed iodination of aryl alkyl ketones using elemental iodineElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b2/b200240j/

  摘要：

  使用元素碘的甲醇溶液和1-氟-4-氯甲基-1,4-二氮杂双环[2.2.2]辛烷双(四氟硼酸)（Selectfluor™ F-TEDA-BF4）处理芳基烷基酮，可以生成相应的α-碘代酮。通过使用乙腈作为溶剂，可以定向调控区域选择性，从而实现对目标分子芳香部分的特定碘化。

  DOI：

  10.1039/b200240j

文献信息

• SelectfluorTM F-TEDA-BF4 mediated and solvent directed iodination of aryl alkyl ketones using elemental iodineElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b2/b200240j/
  作者：Stojan Stavber、Marjan Jereb、Marko Zupan

  DOI：10.1039/b200240j

  日期：2002.2.27

  Reactions of aryl alkyl ketones with methanol solution of elemental iodine and 1-fluoro-4-chloromethyl-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™ F-TEDA-BF4) result in the formation of corresponding α-iodo ketones, while switch over of the regioselectivity can be directed by using acetonitrile as the solvent and selective iodination of the aromatic site of target molecules is thus achieved.

  使用元素碘的甲醇溶液和1-氟-4-氯甲基-1,4-二氮杂双环[2.2.2]辛烷双(四氟硼酸)（Selectfluor™ F-TEDA-BF4）处理芳基烷基酮，可以生成相应的α-碘代酮。通过使用乙腈作为溶剂，可以定向调控区域选择性，从而实现对目标分子芳香部分的特定碘化。
• Ruthenium Chloride as an Efficient Catalytic Precursor for Hydroarylation Reactions via C−H bond Activation
  作者：Marc-Olivier Simon、Jean-Pierre Genet、Sylvain Darses

  DOI：10.1021/ol101038c

  日期：2010.7.2

  A very simple and efficient catalytic system for the hydroarylation of olefins by aromatic ketones and Michael acceptors using simple and inexpensive ruthenium trichloride as a ruthenium source is described. These very mild conditions (dioxane at 80 C) appeared to be highly compatible, tolerant, and selective toward various functional groups, and the ease of the protocol is highly convenient for synthetic purposes.