Dimethyl (4-methylpent-2-enoyl)phosphonate | 207846-54-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: Dimethyl (4-methylpent-2-enoyl)phosphonate
• 英文别名: 1-dimethoxyphosphoryl-4-methylpent-2-en-1-one
• CAS: 207846-54-6
• 化学式: C₈H₁₅O₄P
• 分子量: 206.178
• InChiKey: WIPQGFDRTCAAMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 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：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-羟基-1,4-萘醌 、 Dimethyl (4-methylpent-2-enoyl)phosphonate 在 C₂₈H₂₆F₆N₄S 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 1.0h， 生成 (S)-methyl 3-(1,4-dihydro-2-hydroxy-1,4-dioxonaphthalen-3-yl)-4-methylpentanoate
  参考文献：
  名称：

  Organocatalyzed Enantioselective Michael Addition of 2-Hydroxy-1,4-naphthoquinone to β,γ-Unsaturated α-Ketophosphonatesθ

  摘要：

  By employing a cinchonine-based thiourea as catalyst, highly enantioselective Michael addition reactions of 2-hydroxy-1,4-naphthoquinone to beta,gamma-unsaturated alpha-ketophosphonates were realized. The reaction afforded the corresponding beta-substituted carboxylates in excellent yields with high levels of enantioselectivities (94 -> 99% cc) upon quenching the generated parent structures with DBU and MeOH as a second nucleophile.

  DOI：

  10.1021/jo2002825

文献信息

• Design and Applications of <i>N</i>-<i>tert</i>-Butyl Sulfinyl Squaramide Catalysts
  作者：Yao Li、Cyndi Qixin He、Fei-Xiang Gao、Zhen Li、Xiao-Song Xue、Xin Li、K. N. Houk、Jin-Pei Cheng

  DOI：10.1021/acs.orglett.7b00727

  日期：2017.4.7

  A new chiral HBD system, N-tert-butyl sulfinyl squaramide, was designed and synthesized. The core N-tert-butyl sulfinyl squaramide with an 1-aminoindan-2-ol skeleton was found to be an efficient catalyst in the enantioselective Friedel–Crafts alkylation of indoles and acyl phosphonates.

  一种新的手性HBD系统，ñ -叔丁基亚磺酰基squaramide，设计并合成。核心ñ -叔丁基亚磺酰基squaramide与1-氨基茚满-2-醇骨架被发现是在吲哚和酰基膦酸酯的对映选择性的Friedel-Crafts烷基化的有效催化剂。
• Organocatalyzed Enantioselective Michael Addition of 2-Hydroxy-1,4-naphthoquinone to β,γ-Unsaturated α-Ketophosphonatesθ
  作者：Tao Liu、Youming Wang、Guiping Wu、Haibin Song、Zhenghong Zhou、Chuchi Tang

  DOI：10.1021/jo2002825

  日期：2011.5.20

  By employing a cinchonine-based thiourea as catalyst, highly enantioselective Michael addition reactions of 2-hydroxy-1,4-naphthoquinone to beta,gamma-unsaturated alpha-ketophosphonates were realized. The reaction afforded the corresponding beta-substituted carboxylates in excellent yields with high levels of enantioselectivities (94 -> 99% cc) upon quenching the generated parent structures with DBU and MeOH as a second nucleophile.