dipropyl bromomalonate | 85310-87-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dipropyl bromomalonate
• 英文别名: di-n-propyl bromomalonate；bromo-malonic acid dipropyl ester；Brom-malonsaeure-dipropylester；Dipropyl 2-bromopropanedioate
• CAS: 85310-87-8
• 化学式: C₉H₁₅BrO₄
• 分子量: 267.12
• InChiKey: HCSFNVNYMOUJLF-UHFFFAOYSA-N

物化性质

• 沸点：
  262.6±20.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  dipropyl bromomalonate 在 silver nitrate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 22.0h， 生成 dipropyl ketomalonate
  参考文献：
  名称：

  Kochergin, P. M.; Titkova, R. M., Russian Journal of Organic Chemistry, 1994, vol. 30, # 7.1, p. 1042 - 1044

  摘要：

  DOI：
• 作为产物：
  描述：

  丙二酸二丙酯 生成 dipropyl bromomalonate
  参考文献：
  名称：

  Hirst; Macbeth, Journal of the Chemical Society, 1922, vol. 121, p. 910

  摘要：

  DOI：

文献信息

• Synthesis and study of trannulene derivatives of fullerenes
  作者：E. A. Khakina、A. S. Peregudov、S. I. Troyanov、P. A. Troshin

  DOI：10.1007/s11172-012-0038-1

  日期：2012.2

  A series of trannulenes C60F15[CX(COOR)2]3 (X = COOMe, Br; R = Me, Et, Prn, n-Hex, But, (CH2)3NHCOOBut) was synthesized. The first water-soluble trannulenes containing six carboxyl groups (C60F15[C(COOMe)(COOH)2]3) or six protonated amino groups (C60F15[C(COOMe)(COO(CH2)3NH3 +CF3COO−)2]3) were obtained. The compositions and structures of all compounds were proved by mass spectrometry, 1H, 13C, and 19F NMR spectroscopy, and other physicochemical methods. The reactivity of trannulenes was studied for the first time. The unique isomerization of trannulenes to triumphenes accompanied by the migration of three organic addends from one hemisphere of the fullerene cage to another hemisphere was discovered. The structures of the isomerization products were proved using single-crystal X-ray diffraction analysis and 1H, 13C, and 19F NMR spectroscopy. The concerted cascade of isomerization, elimination, and addition reactions was accomplished, which made it possible to obtain photoactive dyads C60F14R2=A (R = C(X)(COOR)2, A is a fragment of fullerenes C60 or C70, anthracene, or pentacene). These dyads contain the electron-deficient fluorofullerene core and electron-donor (with respect to the fluorofullerene core of the molecule) addend A. Photoinduced charge separation can occur in these systems, which makes them analogs of natural photosynthetic antennas.

  合成了一系列trannulenes C60F15[CX(COOR)2]3 (X = COOMe, Br; R = Me, Et, Prn, n-Hex, But, (CH2)3NHCOOBut)。首先获得了含六个羧基（C60F15[C(COOMe)(COOH)2]3）或六个质子化氨基（C60F15[C(COOMe)(COO(CH2)3NH3 +CF3COO−)2]3）的水溶性trannulenes。所有化合物的组成和结构都通过质谱、1H、13C和19F核磁共振谱和其他物理化学方法得到证明。首次研究了trannulenes的反应活性，发现了trannulenes独特的异构化反应，伴随着三个有机加成物从一个富勒烯笼半球迁移到另一个半球，生成了triumphenes。通过单晶X射线衍射分析和1H、13C和19F核磁共振谱证明了异构化产物的结构。协同的级联异构化、消除和加成反应得以完成，从而有可能获得光活性的二聚体C60F14R2=A (R = C(X)(COOR)2, A是富勒烯C60或C70、蒽或并五苯的片段)。这些二聚体含有缺电子的氟富勒烯核心和相对于氟富勒烯分子核心的电子供体加成物A。在这些系统中可以发生光诱导的电荷分离，使它们成为天然光合天线的类似物。
• Catalytic Asymmetric Hydroacyloxylation/Ring-Opening Reaction of Ynamides, Acids, and Aziridines
  作者：Xiangqiang Li、Hongkun Zeng、Lili Lin、Xiaoming Feng

  DOI：10.1021/acs.orglett.1c00631

  日期：2021.4.16

  A highly enantioselective three-component reaction of ynamides with carboxylic acids and 2,2′-diester aziridines has been realized by using a chiral N,N′-dioxide/Ho(OTf)3 complex as a Lewis acid catalyst. The process includes the formation of an α-acyloxyenamide intermediate through the addition of carboxylic acids to ynamides and the following enantioselective nucleophilic addition to in-situ-generated

  通过使用手性N，N′-二氧化物/ Ho（OTf）3络合物作为路易斯酸催化剂，实现了酰胺与羧酸和2,2'-二酯氮丙啶的高对映选择性三组分反应。该方法包括通过将羧酸加成到酰胺中并随后将对映选择性亲核加成到由手性催化剂诱导的原位生成的甲亚胺基团上来形成α-酰亚氧酰胺中间体。一系列氨基酰氧酰胺以中等至良好的收率和良好的ee值传递。另外，提出了具有过渡模型的可能的催化循环以阐明反应机理。
• Asymmetric synthesis of functionalized 2,3-dihydrobenzofurans using salicyl <i>N</i>-phosphonyl imines facilitated by group-assisted purification (GAP) chemistry
  作者：Hossein Rouh、Yao Tang、Sai Zhang、Ahmed I. M. Ali、Daniel Unruh、Kazimierz Surowiec、Guigen Li

  DOI：10.1039/d1ob02078a

  日期：——

  A new asymmetric method for the synthesis of highly functionalized 2,3-dihydrobenzofuranes in good to high yields and excellent diastereoselectivity via group-assisted purification (GAP) chemistry.

  一种新的不对称方法，通过群辅助纯化（GAP）化学反应，在良好至高收率和优异的对映选择性下合成高度官能化的2,3-二氢苯并呋喃。
• Gallus; Macbeth, Journal of the Chemical Society, 1937, p. 1811
  作者：Gallus、Macbeth

  DOI：——

  日期：——
• Hirst; Macbeth, Journal of the Chemical Society, 1922, vol. 121, p. 910
  作者：Hirst、Macbeth

  DOI：——

  日期：——