N-formylazetidine | 51599-70-3

• 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: N-formylazetidine
• 英文别名: Azetidine-1-carbaldehyde
• CAS: 51599-70-3
• 化学式: C₄H₇NO
• 分子量: 85.1057
• InChiKey: SVTPHAFLJUCRLW-UHFFFAOYSA-N

物化性质

• 沸点：
  40-42 °C(Press: 2 Torr)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,7-diphenyl-4-oxahepta-1,6-diyne 、 N-formylazetidine 在 cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 20.0h， 以37%的产率得到
  参考文献：
  名称：

  钌催化 1,6-二炔与甲酰胺的烃基甲酰化环化

  摘要：

  钌催化的 1,6-二炔与甲酰胺的烃甲酰化环化得到具有 100% 立体选择性的环外二烯型 α,β,γ,δ-不饱和酰胺。提出了一种涉及氢化钌物质的合理机制来解释实验结果。一些使用 DMF-d7 和/或 D2O 进行的控制实验证实了所提出的机制。

  DOI：

  10.1246/cl.160961
• 作为产物：
  描述：

  杂氮环丁烷 、 氯仿 在 四丁基氟化铵 sodium hydroxide 作用下， 反应 1.33h， 以20%的产率得到N-formylazetidine
  参考文献：
  名称：

  Gol'dberg, Yu. Sh.; Shimanskaya, M. V., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, # 10, p. 1789 - 1794

  摘要：

  DOI：

文献信息

• Transformation Routes of P ^V ‐ and P ^III ‐ <i>N</i> ‐Substituted Acyclic Diaminocarbenes
  作者：Anatoliy Marchenko、Georgyi Koidan、Anastasiya Hurieva、Yurii Vlasenko、Alexander B. Rozhenko、Jean‐Marc Sotiropoulos、Aleksandr Kostyuk

  DOI：10.1002/ejic.201801141

  日期：2019.3.31

  Herein we report on the synthesis of a set of transient N‐(PIII)‐phosphanyl and N‐(PV)‐phosphoroselenoyl acyclic diaminocarbenes by deprotonation of the corresponding formamidinium salts. It is shown that N‐(PV)‐substituted acyclic diaminocarbenes undergo 1,2‐phosphorus shift. Transformations of N‐(PIII)‐substituted acyclic diaminocarbenes result in tetrahydroquinazolines as final products. The proposed

  在这里，我们报告了通过相应的甲ami盐的去质子化反应，合成了一组瞬态N-（P III）-膦酰基和N-（P V）-磷核糖酰基无环二氨基卡宾的过程。结果表明，N-（P V）-取代的无环二氨基碳烯经历了1,2-磷的迁移。N-（P III的变换）-取代的无环二氨基卡宾生成四氢喹唑啉作为终产物。拟议的机制包括将羧甲基异构化为瞬时的甲亚胺基团，然后通过亲电子芳族取代将其环化。将给电子的二甲氨基基团引入苯基取代基可显着提高反应速度和最终产物的收率。在吗啉衍生物的情况下，相应的甲亚胺叶立德经历了吗啉环的打开，生成乙烯基恶唑烷-2-胺。DFT计算结果证实了这一结果。
• A Facile Syntehsis of 2-Substituted Azetidines
  作者：Tatsuya Shono、Yoshihiro Matsumura、Kenshi Uchida、Fumihiko Nakatani

  DOI：10.1246/bcsj.61.3029

  日期：1988.8

  A new method for the synthesis of 2-substituted azetidines has been exploited. The method consists of (1) anodic acetoxylation of 1-(p-tolylsulfonyl)azetidine at the 2-position and (2) subsequent nucleophilic substitution of the acetoxyl group with nucleophiles such as trimethylsilyl cyanide, allyltrimethylsilane, 2-acetoxyfuran, and trimethyl phosphite.

  开发了一种合成2-取代氮杂环丁烷的新方法。该方法包括 (1) 1-(对甲苯磺酰基)氮杂环丁烷在 2 位进行阳极乙酰氧基化，以及 (2) 随后用三甲基氰硅烷、烯丙基三甲基硅烷、2-乙酰氧基呋喃和亚磷酸三甲酯等亲核试剂对乙酰氧基进行亲核取代。
• Reaction of Aminocarbene Complexes of Chromium with Alkynes. 5. Influence of the Ring Size on the Product Distribution. Formation of Pyrroles from Pyrrolidine and Its Derivative-Substituted Carbene Complexes
  作者：Andree Parlier、Michele Rudler、Henri Rudler、Regis Goumont、Jean-Claude Daran、Jacqueline Vaissermann

  DOI：10.1021/om00006a024

  日期：1995.6

  A series of aminocarbene complexes of chromium derived from piperidine (1), hexa- and heptamethyleneimine (4) and (8), pyrrolidine (13a-d, R(1) = Me, H, Ph, thienyl), perhydroindole (21), thiazolidine (24a,b, R(1) = Me, Ph), pyrroline (30a,b), and azetidine (33a-e and 36) have been synthesized and subjected to alkyne insertion reactions. Aminocarbene complex 24a-E has been fully characterized by X-ray structure analysis. Crystal data for 24a-E: C10H9O5NSCr, monoclinic, space group P2(1)/n, a = 8.3011(9) Angstrom, b = 11.949(1) Angstrom, c = 13.101(2) Angstrom, beta = 95.74(1)degrees, V = 1293(1) Angstrom(3), d(calcd) = 1.41 g cm(-3), Z = 4. Whereas complex 1 reacted with diphenylacetylene to give first the ylide complex 2, the thermolysis of which led to the bridgehead lactam 3, complexes 4, and 8 gave directly the expected bridgehead lactams 6 and 11. The structure of 3 has been determined by X-ray diffraction. Crystal data for 3: C27H25ON, monoclinic, space group P2(1)/c, a = 10.080(4) Angstrom, b = 11.727(3) Angstrom, c 18.014(6) Angstrom, beta = 102.40(3)degrees, V = 2080(14) Angstrom(3), d(calcd) = 1.21 g cm(-3), Z = 4. In contrast to 1, 4, and 8, all of the new carbene complexes derived from five-membered cycloamines except 24b gave pyrrole derivatives as the result of the alkyne/CO insertion followed by migration of an alkyl chain from nitrogen to the carbon atom of the inserted carbonyl group and loss of its oxygen atom. The structures of 14a, the Cr(CO)(3) complex of 15a, and 22 could be unambiguously established by X-ray crystallography. Crystal data for 15: C24H21O3NCr, triclinic, space group P1, a = 6.918(1) Angstrom, b = 10.057(1) Angstrom, c = 15.193(2) Angstrom, alpha = 72.410(9)degrees, beta = 84.99(1)degrees, gamma = 84.66(3)degrees, V = 1001(3) Angstrom(3), d(calcd) = 1.40 g cm(-3), Z = 2. For 22: C24H25N, monoclinic, space group P2(1)/n, a = 11.119(3) Angstrom, b = 10.682(2) Angstrom, c = 15.428(3) Angstrom, beta = 102.23(2)degrees, V = 1791(7) Angstrom(3), d(calcd) = 1.21 g cm(-3), Z = 4. Besides these pyrroles, the expected bridgehead lactams 17a-d were isolated from 13a-d together with the lactone complex 18 in the case of 13b. Crystal data for 18: C19H12O5Cr, orthorhombic, space group Pc2(1)/b, a = 10.356(1) Angstrom, b = 12.366(5) Angstrom, c = 12.529(2) Angstrom, V = 1604.4(8) Angstrom(3), d(calcd) = 1.54 g cm(-3), Z = 4. However, 24b gave as the major insertion product the aminofuran 26, and pyrroline-derived carbene complexes 30a,b gave lactams 32a,b and trace amounts of pyrroles 31a,b. Only trace amounts of pyrroles were detected starting from carbene complexes derived from azetidine (33a-e) and 36, which gave mainly the lactams 35a,d and 37. Mechanisms for these new transformations of aminocarbene complexes of chromium based on the behavior of the Stevens-type acyl-stabilized N-ylides will be suggested.
• Blum, Zoltan; Malmberg, Mats; Nyberg, Klas, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1981, vol. 35, # 10, p. 739 - 741
  作者：Blum, Zoltan、Malmberg, Mats、Nyberg, Klas

  DOI：——

  日期：——
• GOLDBERG, YU. SH.;SHIMANSKAYA, M. V., ZH. ORGAN. XIMII, 1982, 18, N 10, 2036-2042
  作者：GOLDBERG, YU. SH.、SHIMANSKAYA, M. V.

  DOI：——

  日期：——