1-formyl-3-phenylazetidine | 165612-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-formyl-3-phenylazetidine
• 英文别名: 3-Phenylazetidine-1-carbaldehyde
• CAS: 165612-02-2
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: QYFMZMSMCFIVKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  disodium pentacarbonylchromium 、 1-formyl-3-phenylazetidine 以 not given 为溶剂， 以50%的产率得到
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/om00006a024

文献信息

• [EN] CYANOPYRROLIDINE DERIVATIVES WITH ACTIVITY AS INHIBITORS OF USP30<br/>[FR] DÉRIVÉS DE CYANOPYRROLIDINE AYANT UNE ACTIVITÉ EN TANT QU'INHIBITEURS DE L'USP 30
  申请人：MISSION THERAPEUTICS LTD

  公开号：WO2018060689A1

  公开（公告）日：2018-04-05

  The present invention relates to substituted-cyanopyrrolidines of Formula (I) with activity as inhibitors of deubiquitilating enzymes, in particular, ubiquitin C-terminal hydrolase 30 or ubiquitin specific peptidase 30 (USP30), having utility in a variety of therapeutic areas including cancer and conditions involving mitochondrial dysfunction. (I)

  本发明涉及一种具有抑制去泛素化酶活性的Formula(I)的替代氰基吡咯烷化合物，特别是泛素C-末端水解酶30或泛素特异性肽酶30（USP30），在包括癌症和涉及线粒体功能障碍在内的各种治疗领域具有实用性。
• CYANOPYRROLIDINE DERIVATIVES WITH ACTIVITY AS INHIBITORS OF USP30
  申请人：Mission Therapeutics Limited

  公开号：EP3519385B1

  公开（公告）日：2020-11-18