1-diazo-6-methyl-2,5-heptanedione | 1227874-31-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-diazo-6-methyl-2,5-heptanedione
• 英文别名: 1-Diazo-6-methylheptane-2,5-dione；1-diazo-6-methylheptane-2,5-dione
• CAS: 1227874-31-8
• 化学式: C₈H₁₂N₂O₂
• 分子量: 168.195
• InChiKey: XHSBLQBEGDHRIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  36.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-diazo-6-methyl-2,5-heptanedione 、 4-formylphenyl methanesulfonate 在 Rh₂(S-BPTV)4*2THF 作用下， 以 三氟甲苯 为溶剂， 反应 0.08h， 生成 4-((1R,5S,7S)-5-isopropyl-2-oxo-6,8-dioxabicyclo[3.2.1]octan-7-yl)phenyl methanesulfonate 、
  参考文献：
  名称：

  使用羰基叶立德环加成策略催化不对称构建 Psoracorylifols B 和 C 的 exo-7-Aryl-6,8-dioxabicyclo[3.2.1]octane 骨架

  摘要：

  因此，由手性二铑 (II) 配合物催化的该序列的对映选择性版本的开发已成为一个具有挑战性的目标。在这个过程中，手性二铑（II）催化剂必须能够在环加成步骤中与羰基叶立德中间体缔合，

  DOI：

  10.5012/bkcs.2010.31.03.694

文献信息

• Inverse electron demand asymmetric cycloadditions of cyclic carbonyl ylides catalyzed by chiral Lewis acids—Scope and limitations of diazo and olefinic substrates
  作者：Hiroyuki Suga、Satoshi Higuchi、Motoo Ohtsuka、Daisuke Ishimoto、Tadashi Arikawa、Yuta Hashimoto、Shunta Misawa、Teruko Tsuchida、Akikazu Kakehi、Toshihide Baba

  DOI：10.1016/j.tet.2010.01.095

  日期：2010.4

  enantioselectivities (73–97% ee) were also obtained for the cycloadditions between 3-acyl-2-benzopyrylium-4-olates, generated from methyl 2-(2-diazo-1,3-dioxoalkyl)benzoates and butyl or cyclohexyl vinyl ethers, in the presence of binaphthyldiimine (BINIM)–Ni(II) complexes (10 mol %). Under similar conditions, the reaction between methyl 2-(2-diazo-1,3-dioxohexyl)benzoate and 2,3-dihydrofuran was highly

  通过Rh 2（OAc）4催化邻甲氧基羰基分解生成的环己基乙烯基醚与2-苯并吡啶-4-醇酸酯之间的反电子需求的1,3-偶极环加成反应，获得了高对映选择性（94-96％ee）-α-重氮苯乙酮。该反应有效地催化的Eu（OTF）3，何（OTF）3，或Gd（OTF）3种性2,6-二复合物（10摩尔％）[（4-小号，5小号）-4,5-二苯基-2-恶唑啉基]吡啶。与其他富电子偶极亲子的反应，例如烯丙醇，2,3-二氢呋喃和丁基叔丁基丁基二甲基甲硅烷基乙烯酮缩醛显示中等的对映体选择性（60-73％ee）。还获得了由2-（2-重氮-1,3-二氧代烷基）苯甲酸甲酯和丁酯生成的3-酰基-2-苯并吡啶-4-醇酸酯之间的环加成反应，具有良好的对映选择性（73-97％ee）。环己基乙烯基醚，在联萘胺（BINIM）-Ni（II）络合物（10摩尔％）的存在下。在类似条件下，2-（2-重氮基-1,3- dioxohexyl）苯甲酸乙酯和2
• Chiral Lewis Acid-Catalyzed Enantioselective Cycloadditions between Indoles and Cyclic Carbonyl Ylides Derived from Diazodiketone or Diazoketoester Derivatives
  作者：Hiroyuki Suga、Yurie Sekikawa、Shunta Misawa、Daito Kinugawa、Rinnosuke Oda、Kennosuke Itoh、Yasunori Toda、Ryotaro Kiyono

  DOI：10.1021/acs.joc.5b00835

  日期：2015.7.2

  Asymmetric 1,3-dipolar cycloaddition reactions between N-methylindoles and several cyclic carbonyl ylides that were derived from diazodiketone or diazoketoester precursors in the presence of both achiral Rh and chiral lanthanoid metal catalysts are described. For the six-membered cyclic carbonyl ylides derived from 1-diazo-5-aryl-2,5-pentanedione precursors, the cycloaddition reactions were carried out using Rh-2(OAc)(4) (2 mol %) and the chiral Pybox-Ph-2 -Lu(OTf)(3) complex (10 mol %) as catalysts, resulting in high enantioselectivities (83% to >98% ee (exo)) along with relatively good exo-selectivities (exo:endo = 65:35 to 94:6) and yields (63-85%). For the five-membered cyclic carbonyl ylide derived from bromo-1-methylindole was carried out in the presence of Rh-2(OAc)(4) (2 mol%) and chiral Pybox-Ph-2-Er(OTf)(3) complex (30 mol %) as catalysts, resulting in relatively good enantioselectivity (78% ee) and endo-selectivity (endo:exo = 81:19).
• Catalytic Asymmetric Construction of the exo-7-Aryl-6,8-dioxabicyclo[3.2.1]octane Framework of Psoracorylifols B and C Using a Carbonyl Ylide Cycloaddition Strategy
  作者：Yasunobu Kurosaki、Naoyuki Shimada、Masahiro Anada、Hisanori Nambu、Shunichi Hashimoto

  DOI：10.5012/bkcs.2010.31.03.694

  日期：2010.3.20

  Conse-quently, the development of an enantioselective version of this sequence catalyzed by chiral dirhodium(II) complexes has be-come a challenging objective. In this process, the chiral dirho-dium(II) catalyst must be capable of associating with carbonyl ylide intermediates in the cycloaddition step,

  因此，由手性二铑 (II) 配合物催化的该序列的对映选择性版本的开发已成为一个具有挑战性的目标。在这个过程中，手性二铑（II）催化剂必须能够在环加成步骤中与羰基叶立德中间体缔合，