1,2,3,4-tetrahydronaphthalene-1,2-diyl diacetate | 667894-33-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2,3,4-tetrahydronaphthalene-1,2-diyl diacetate
• 英文别名: 1,2-diacetoxytetrahydronaphthalene；1,2-Diacetoxytetralin；(1-acetyloxy-1,2,3,4-tetrahydronaphthalen-2-yl) acetate
• CAS: 667894-33-9
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: PWDTYDXUIYVSGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydronaphthalene-1,2-diyl diacetate 在 氢氧化钾 作用下， 生成 (1S,2R)-cis-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Straus; Rohrbacher, Chemische Berichte, 1921, vol. 54, p. 57

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-二氢萘 、 碘苯二乙酸 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 16.0h， 以75%的产率得到1,2,3,4-tetrahydronaphthalene-1,2-diyl diacetate
  参考文献：
  名称：

  Copper-Catalyzed Diacetoxylation of Olefins using PhI(OAc)₂ as Oxidant

  摘要：

  Copper(I) or -(II) salts with weakly coordinating anions catalyze the diacetoxylation of olefins efficiently in the presence of PhI(OAc)(2) as the oxidant under mild conditions, The reaction is effective for aryl, aryl alkyl, as well as aliphatic terminal and internal olefins forming the corresponding vicinal diacetoxy compounds in 70-85% yields and dr (syn/anti) of up to 5.2. Under these conditions, homoallylic alcohols formed the corresponding tetrahydrofuran derivatives in high yields.

  DOI：

  10.1021/ol902813m

文献信息

• Triflic Acid Catalyzed Oxidative Lactonization and Diacetoxylation of Alkenes Using Peroxyacids as Oxidants
  作者：Yan-Biao Kang、Lutz H. Gade

  DOI：10.1021/jo202491y

  日期：2012.2.3

  A clean and efficient diacetoxylation reaction of alkenes catalyzed by triflic acid using commercially available peroxyacids as the oxidants has been developed. This method was also applied in oxidative lactonizations of unsaturated carboxylic acids in good to high yields.

  已经开发了使用可商购的过氧酸作为氧化剂的三氟甲磺酸催化的烯烃的清洁且有效的二乙酰氧基化反应。该方法还以高产率到高产率用于不饱和羧酸的氧化内酯化。
• Iron-Catalyzed Dioxygenation of Alkenes and Terminal Alkynes by using (Diacetoxyiodo)benzene as Oxidant
  作者：B. T. V. Srinivas、Vikas S. Rawat、Bojja Sreedhar

  DOI：10.1002/adsc.201500681

  日期：2015.11.16

  syn-diacetoxylation of alkenes and 1,2-oxyacetoxylation of terminal alkynes has been developed using (diacetoxyiodo)benzene as oxidant. A broad range of internal and terminal alkenes, including electron-rich as well as electron-deficient alkenes, gave the desired products in good to excellent yields with high diastereoselectivity (up to >99:1 dr). In addition the high catalytic activity of iron catalysis for the

  使用（二乙酰氧基碘）苯作为氧化剂，已经开发了铁催化的烯烃的顺式-二乙酰氧基化和末端炔的1,2-氧基乙酰氧基化。各种各样的内部和末端烯烃，包括富电子的和缺电子的烯烃，以高至非对映选择性（高达> 99：1 dr）提供了所需的产物，收率良好至优异。另外，还报道了铁催化末端炔烃的1，2-氧乙酰氧基化的高催化活性。评估了催化剂，氧化剂和其他反应参数对不饱和键活化的作用。
• The Nature of the Catalytically Active Species in Olefin Dioxygenation with PhI(OAc)₂: Metal or Proton?
  作者：Yan-Biao Kang、Lutz H. Gade

  DOI：10.1021/ja110805b

  日期：2011.3.16

  Evidence for the protiocatalytic nature of the diacetoxylation of alkenes using PhI(OAc)(2) as oxidant is presented. Systematic studies into the catalytic activity in the presence of proton-trapping and metal-complexing agents indicate that protons act as catalysts in the reaction. Using triflic acid as catalyst, the selectivity and reaction rate of the conversion is similar or superior to most efficient metal-based catalysts. Metal cations, such as Pd(II) and Cu(II), may interact with the oxidant in the initiation phase of the catalytic transformation; however, 1 equiv of strong acid is produced in the first cycle which then functions as the active catalyst. Based on a kinetic study as well as in situ mass spectrometry, a mechanistic cycle for the proton-catalyzed reaction, which is consistent with all experimental data presented in this work, is proposed.
• Horiuchi, C. Akira; Fukushima, Tomoaki; Furuta, Noriyuki, Journal of Chemical Research - Part S, 2003, # 5, p. 270 - 272
  作者：Horiuchi, C. Akira、Fukushima, Tomoaki、Furuta, Noriyuki、Chai, Wen、Ji, Shun-Jun、Saito, Yoshikazu、Hashimoto, Chikao、Takahashi, T. Tomoyoshi、Sugiyama, Takashi、Muto, Akinori、Sakata, Yusaku、Nozaki, Sukekatsu

  DOI：——

  日期：——
• NOVEL COMPOUNDS
  申请人：Smithkline Beecham S.p.A.

  公开号：EP0802897A1

  公开（公告）日：1997-10-29