methyl 2,2-diacetylcyclopropanecarboxylate | 39822-32-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 2,2-diacetylcyclopropanecarboxylate
• 英文别名: Methyl 2,2-diacetylcyclopropane-1-carboxylate；methyl 2,2-diacetylcyclopropane-1-carboxylate
• CAS: 39822-32-7
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: DKZYGWRGAUURRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯代丙烯酸甲酯 、 乙酰丙酮 在 copper(I) oxide 、 异氰酸叔丁酯 作用下， 生成 methyl 2,2-diacetylcyclopropanecarboxylate
  参考文献：
  名称：

  Synthetic reactions by complex catalysts. XXX. Synthesis of cyclic compounds by means of copper-isonitrile complex. Copper(I) carbenoid intermediate

  摘要：

  DOI：

  10.1021/jo00953a011

文献信息

• Domino Michael–O-alkylation reaction: one-pot synthesis of 2,4-diacylhydrofuran derivatives and its application to antitumor naphthofuran synthesis
  作者：Hisahiro Hagiwara、Kouji Sato、Daisuke Nishino、Takashi Hoshi、Toshio Suzuki、Masayoshi Ando

  DOI：10.1039/b107180g

  日期：2001.11.15

  The reaction of enolates of 1,3-dicarbonyl compounds with α-halo-α,β-unsaturated carbonyl compounds affords 2,4-diacyldihydrofuran derivatives in the presence of DBU in THF. Chemical manganese dioxide oxidation of the hydrofurans leads to 2,4-diacylfuran derivatives. Application of the protocol enables short-step syntheses of antitumor naphthofuran natural products.

  在THF中，使用DBU作为催化剂，1,3-二羰基化合物的烯醇盐与α-卤代-α,β-不饱和羰基化合物的反应生成2,4-二酰基二氢呋喃衍生物。通过化学二氧化锰氧化这些二氢呋喃，可以得到2,4-二酰基呋喃衍生物。这一方法的应用使得抗肿瘤的萘呋喃天然产物能够通过简短的步骤合成。
• Cyclopropanation of active methylene compounds with β-alkoxycarbonyl vinylsulfonium salts
  作者：Shenquan Guo、Niuniu Zhang、Xiangzheng Tang、Zhifeng Mao、Xuejing Zhang、Ming Yan、Yining Xuan

  DOI：10.1016/j.cclet.2018.08.021

  日期：2019.2

  Abstract An efficient synthesis of β-alkoxycarbonyl vinylsulfonium salts had been developed. Their reaction with indene-1,3-diones and other active methylene compounds provided cyclopropane carboxylates in good yields. A tentative reaction mechanism was proposed.

  摘要研究了一种高效合成β-烷氧基羰基乙烯基salts盐的方法。它们与茚-1，3-二酮和其他活性亚甲基化合物的反应以良好的收率提供了环丙烷羧酸酯。提出了一种初步的反应机理。
• Tandem nucleophilic reaction of 1,3-dicarbonyl compounds to methyl α-bromoacrylate: [3+2]heteroannulation leading to hydrofuran derivatives
  作者：Hisahiro Hagiwara、Kouji Sato、Toshio Suzuki、Masayoshi Ando

  DOI：10.1016/s0040-4039(97)00317-1

  日期：1997.3

  Enolates of 1,3-dicarbonyl compounds 1 add in a [3+2] manner to methyl alpha-bromoacrylate 2 to furnish hydrofuran derivatives 3 or 4 in the presence of DBU in THF. (C) 1997 Elsevier Science Ltd.
• Synthetic reactions by complex catalysts. XXX. Synthesis of cyclic compounds by means of copper-isonitrile complex. Copper(I) carbenoid intermediate
  作者：Takeo Saegusa、Kazuya Yonezawa、Ichiki Murase、Toshiro Konoike、Shimpei Tomita、Yoshihiko Ito

  DOI：10.1021/jo00953a011

  日期：1973.6