tert-butyldimethyl((4-methylene-1-(prop-2-ynyl)-1,4-dihydronaphthalen-1-yl)methoxy)silane | 1221432-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyldimethyl((4-methylene-1-(prop-2-ynyl)-1,4-dihydronaphthalen-1-yl)methoxy)silane
• 英文别名: Tert-butyl-dimethyl-[(4-methylidene-1-prop-2-ynylnaphthalen-1-yl)methoxy]silane
• CAS: 1221432-94-5
• 化学式: C₂₁H₂₈OSi
• 分子量: 324.538
• InChiKey: YQNXQQCBWYZOOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-butyldimethyl((4-methylene-1-(prop-2-ynyl)-1,4-dihydronaphthalen-1-yl)methoxy)silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到(4-methylene-1-(prop-2-ynyl)-1,4-dihydronaphthalen-1-yl)-methanol
  参考文献：
  名称：

  Propargylic and Allenic Carbocycle Synthesis through Palladium-Catalyzed Dearomatization Reaction

  摘要：

  The dearomatization reaction of benzylic chlorides (1a-k), chloromethylnaphthalenes (1l-r), and naphthalene allyl chlorides (3a-d) with allenyltributyltin proceeded smoothly in the presence of Pd(PPh(3))(4) catalyst at room temperature to give the corresponding propargylated and/or allenylated dearomatization products (5, 5'; 6, 6'; and 7, respectively) in high to fair yields. The reaction of 1a-k proceeded smoothly in the presence of TBAF, whereas it was not necessary to use TBAF as an additive in the reactions of 1l-k and 3a-d. These reactions provided a new and efficient method for the synthesis of propargylic and allenic carbocycles.

  DOI：

  10.1021/jo100211d
• 作为产物：
  描述：

  tert-butyl((4-(chloromethyl)naphthalen-1-yl)methoxy)-dimethylsilane 、 1,2-丙二烯三正丁基锡 在 四(三苯基膦)钯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 tert-butyldimethyl((4-methylene-1-(propa-1,2-dienyl)-1,4-dihydronaphthalen-1-yl)methoxy)silane 、 tert-butyldimethyl((4-methylene-1-(prop-2-ynyl)-1,4-dihydronaphthalen-1-yl)methoxy)silane
  参考文献：
  名称：

  Propargylic and Allenic Carbocycle Synthesis through Palladium-Catalyzed Dearomatization Reaction

  摘要：

  The dearomatization reaction of benzylic chlorides (1a-k), chloromethylnaphthalenes (1l-r), and naphthalene allyl chlorides (3a-d) with allenyltributyltin proceeded smoothly in the presence of Pd(PPh(3))(4) catalyst at room temperature to give the corresponding propargylated and/or allenylated dearomatization products (5, 5'; 6, 6'; and 7, respectively) in high to fair yields. The reaction of 1a-k proceeded smoothly in the presence of TBAF, whereas it was not necessary to use TBAF as an additive in the reactions of 1l-k and 3a-d. These reactions provided a new and efficient method for the synthesis of propargylic and allenic carbocycles.

  DOI：

  10.1021/jo100211d

文献信息

• Propargylic and Allenic Carbocycle Synthesis through Palladium-Catalyzed Dearomatization Reaction
  作者：Bo Peng、Xiujuan Feng、Xin Zhang、Sheng Zhang、Ming Bao

  DOI：10.1021/jo100211d

  日期：2010.4.16

  The dearomatization reaction of benzylic chlorides (1a-k), chloromethylnaphthalenes (1l-r), and naphthalene allyl chlorides (3a-d) with allenyltributyltin proceeded smoothly in the presence of Pd(PPh(3))(4) catalyst at room temperature to give the corresponding propargylated and/or allenylated dearomatization products (5, 5'; 6, 6'; and 7, respectively) in high to fair yields. The reaction of 1a-k proceeded smoothly in the presence of TBAF, whereas it was not necessary to use TBAF as an additive in the reactions of 1l-k and 3a-d. These reactions provided a new and efficient method for the synthesis of propargylic and allenic carbocycles.