3-iodo-2,5-dimethyl-1,4-benzoquinone | 7294-86-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-iodo-2,5-dimethyl-1,4-benzoquinone
• 英文别名: 2,5-Dimethyl-3-iodo-1,4-benzoquinone；3-iodo-2,5-dimethylcyclohexa-2,5-diene-1,4-dione
• CAS: 7294-86-2
• 化学式: C₈H₇IO₂
• 分子量: 262.047
• InChiKey: CSTAKSOITBGQEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  81-82 °C
• 沸点：
  268.6±35.0 °C(Predicted)
• 密度：
  1.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-iodo-2,5-dimethyl-1,4-benzoquinone 、 1,3-环己二烯 在 triflimide activated chiral oxazaborolidine 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以99%的产率得到(1S,2R,7S,8R)-4-iodo-2,5-dimethyl-tricyclo[6.2.2.0^2,7]dodeca-4,9-diene-3,6-dione
  参考文献：
  名称：

  Triflimide Activation of a Chiral Oxazaborolidine Leads to a More General Catalytic System for Enantioselective Diels−Alder Addition

  摘要：

  The strong acid triflimide ((CF3SO2)2NH) protonates chiral oxazaborolidines to form superactive, stable, chiral Lewis acids which are highly effective catalysts for a wide variety of enantioselective Diels-Alder reactions, documented herein by more than 20 examples.

  DOI：

  10.1021/ja035393r
• 作为产物：
  描述：

  4,6-二碘-2,5-二甲基-苯酚 在 potassium dichromate 、 溶剂黄146 作用下， 生成 3-iodo-2,5-dimethyl-1,4-benzoquinone
  参考文献：
  名称：

  Bordeianu, Annales Scientifiques de l'Universite de Jassy, Section 1: Mathematiques, Physique, Chimie, 1937, vol. 23, p. 240,242, 243

  摘要：

  DOI：

文献信息

• Chiral Oxazaborolidine−Aluminum Bromide Complexes Are Unusually Powerful and Effective Catalysts for Enantioselective Diels−Alder Reactions
  作者：Duan Liu、Eda Canales、E. J. Corey

  DOI：10.1021/ja068637r

  日期：2007.2.1

  acid catalyst than protonated 1 (i.e., 2) for enantioselective Diels−Alder reactions. Only 4 mol % of catalyst 3 is required to achieve yields and enantiomeric purities of 90% over a broad range of achiral dienes and dienophiles. The ligand from which 3 is derived can be recovered easily and with high efficiency. The method is illustrated by 22 examples.

  用 AlBr3 处理手性 oxazaborolidine 1 生成 1:1 配合物 3，这是一种比质子化 1（即 2）更有效的路易斯酸催化剂，用于对映选择性 Diels-Alder 反应。仅需要 4 mol% 的催化剂 3 即可在广泛的非手性二烯和亲二烯体上实现 90% 的产率和对映体纯度。衍生出 3 的配体可以轻松高效地回收。该方法通过 22 个示例进行说明。
• General Methodology for the Preparation of Unsymmetrical α-Linked Bisenones via Ligandless Cross-Coupling Reactions
  作者：David R. Williams、Seth A. Bawel

  DOI：10.1021/acs.orglett.7b00497

  日期：2017.4.7

  A stereocontrolled Stille cross-coupling reaction, involving the use of Pd2dba3, provides a general procedure for the synthesis of unsymmetrical α-linked bisenone systems. The transformation is achieved in the absence of phosphine ligands under conditions that promote the stabilization of “ligandless” palladium catalysis. The extension of these studies illustrates Suzuki–Miyaura reactions of 2-bor

  涉及使用Pd 2 dba 3的立体控制的Stille交叉偶联反应为合成不对称的α-连接的Bisenone系统提供了一般步骤。在促进“无配体”钯催化作用稳定的条件下，在不存在膦配体的情况下完成转化。这些研究的扩展说明了2-硼基-2-环己烯-1-酮与碘化物和三氟甲磺酸酯伙伴的Suzuki-Miyaura反应，用于合成新型电子缺陷型1,3-二烯。
• Enantioselective and Structure-Selective Diels−Alder Reactions of Unsymmetrical Quinones Catalyzed by a Chiral Oxazaborolidinium Cation. Predictive Selection Rules
  作者：Do Hyun Ryu、Gang Zhou、E. J. Corey

  DOI：10.1021/ja049323b

  日期：2004.4.1

  The chiral oxazaborolidinium cation 1 promotes Diels-Alder reactions between 2-triisopropylsilyloxy-1,3-butadiene and a number of unsymmetrical 1,4-benzoquinones in a highly enantioselective and structurally selective manner. The basis for the enantioselectivity is explained rationally in terms of a preferred type of transition-state assembly. Selection rules have been developed that allow the prediction of the principal reaction product of Diels-Alder reaction between unsymmetrical diene and quinone components.
• Triflimide Activation of a Chiral Oxazaborolidine Leads to a More General Catalytic System for Enantioselective Diels−Alder Addition
  作者：Do Hyun Ryu、E. J. Corey

  DOI：10.1021/ja035393r

  日期：2003.5.1

  The strong acid triflimide ((CF3SO2)2NH) protonates chiral oxazaborolidines to form superactive, stable, chiral Lewis acids which are highly effective catalysts for a wide variety of enantioselective Diels-Alder reactions, documented herein by more than 20 examples.
• Bordeianu, Annales Scientifiques de l'Universite de Jassy, Section 1: Mathematiques, Physique, Chimie, 1937, vol. 23, p. 240,242, 243
  作者：Bordeianu

  DOI：——

  日期：——