2-hydroxymethylquinoline-3-carboxylic acid lactone | 4945-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-hydroxymethylquinoline-3-carboxylic acid lactone
• 英文别名: Furo<3,4-b>quinolin-1(3H)-one；furo[3,4-b]quinolin-1(3H)-one；3H-Furo[3,4-b]chinolin-1-on；3H-furo[3,4-b]quinolin-1-one；3H-Furo[3,4-b]chinolin-1-on；1-Oxo-1,3-dihydro-furo<3.4-b>chinolin；3H-furo[3,4-b]quinolin-1-one
• CAS: 4945-38-4
• 化学式: C₁₁H₇NO₂
• 分子量: 185.182
• InChiKey: FZYGATLKLHAMAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxymethylquinoline-3-carboxylic acid lactone 在 sodium hydroxide 、 正丁基锂 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 indolo<6,7-b>oxepino<3,4-b>quinolin-13(6H,12H)-one
  参考文献：
  名称：

  Ashcroft, William R.; Dalton, Lesley; Beal, Michael G., Journal of the Chemical Society. Perkin transactions I, 1983, # 10, p. 2409 - 2412

  摘要：

  DOI：
• 作为产物：
  描述：

  8-(2-Nitrophenyl)-1,3,5,7-tetrahydro-8H-difuro[3,4-b;3',4'-e]pyran-1,7-dion 在 盐酸 、 tin 作用下， 以 甲醇 、 水 为溶剂， 反应 2.5h， 生成 2-hydroxymethylquinoline-3-carboxylic acid lactone
  参考文献：
  名称：

  Goerlitzer; Trittrmacher; Bartke, Pharmazie, 2002, vol. 57, # 9, p. 606 - 609

  摘要：

  DOI：

文献信息

• Tricyclic dihydroquinoline derivatives,method for preparing same and pharmaceutical compositions containing same
  申请人：——

  公开号：US20040198981A1

  公开（公告）日：2004-10-07

  Compound of formula (I): 1 wherein: 2 represents a single or double bond, 3 represents a ring system selected from 4 R 6a , R 6b , R 6c , R 6d , X and Y are as defined in the description, R 1 represents a hydrogen atom or a group selected from aryl, heteroaryl, cycloalkyl, optionally substituted alkyl, and COR 8 wherein R 8 is as defined in the description, R 2 , R 3 , R 4 and R 5 , which may be the same or different, each represent: a hydrogen atom, a halogen atom, an alkyl group,. an alkoxy group, a hydroxy group, a polyhaloalkyl group, a nitro group, an optionally substituted amino group, a group of formula 5 wherein m represents an integer such that 1≦m≦4, or R 2 with R 3 , or R 3 with R 4 , or R 4 with R 5 , form, together with the carbon atoms carrying them, an optionally substituted, 5- to 12-membered, mono- or bi-cyclic, aromatic or non-aromatic group optionally containing 1 or 2 hetero atoms selected from O, S and N, R 10 represents a hydrogen atom or an alkyl group, Ar represents an aryl, heteroaryl or arylalkyl group, its optical isomers, addition salts thereof with a pharmaceutically acceptable acid, and hydrates and solvates thereof.

  化合物的式子（I）：其中：代表单键或双键，代表从R6a，R6b，R6c，R6d选择的环系统，X和Y的定义在描述中，R1代表氢原子或从aryl，heteroaryl，cycloalkyl，可选择的取代烷基和COR8中选择的基团，其中R8在描述中定义，R2，R3，R4和R5，可以相同也可以不同，每个代表：氢原子，卤原子，烷基，烷氧基，羟基，多卤代烷基，硝基，可选择的取代氨基，式子5中m代表整数，使得1≤m≤4，或R2与R3，或R3与R4，或R4与R5，与携带它们的碳原子一起形成，一个可选择取代的，含有1或2个从O，S和N选择的杂原子的，5到12个成员的，单环或双环的，芳香或非芳香基团，R10代表氢原子或烷基，Ar代表芳基，杂原芳基或芳基烷基，它的光学异构体，与药学上可接受的酸形成的加合盐，以及其水合物和溶剂合物。
• Enantioselective Organocatalytic Partial Transfer Hydrogenation of Lactone-Fused Quinolines
  作者：Alexandre Aillerie、Vincent Lemau de Talancé、Aurélien Moncomble、Till Bousquet、Lydie Pélinski

  DOI：10.1021/ol5011196

  日期：2014.6.6

  The first enantioselective synthesis of 4-aza-podophyllotoxin derivatives by partial transfer hydrogenation of lactone-fused quinolines was achieved using a chiral Brønsted acid catalyst. This reaction was extended to a large scope of substrates with good yields and enantioselectivities.

  使用手性布朗斯台德酸催化剂，通过内酯融合的喹啉的部分转移氢化，首次进行4-氮杂-鬼臼毒素衍生物的对映选择性合成。该反应以良好的产率和对映选择性扩展到大范围的底物。
• Novel tricyclic dihydro-quinoline derivatives, method for preparing same and pharmaceutical compositions containing the same
  申请人：——

  公开号：US20040180917A1

  公开（公告）日：2004-09-16

  A compound of formula (I): 1 wherein: 2 represents a single or double bond, 3 represents a ring system selected from 4 5 R 9a , R 9b , R 9c , X and Y are as defined in the description, R 1 represents a group selected from hydrogen, aryl, heteroaryl, cycloalkyl, optionally substituted alkyl, and COR 11 , wherein R 11 is as defined in the description, R 2 to R 8 each represent a group selected from hydrogen, halogen, hydroxy, polyhaloalkyl, nitro, optionally substituted alkyl, optionally substituted amino, optionally substituted alkoxy, —OPO(OH) 2 and 6 wherein m represents an integer such that 1≦m<4, or R 2 with R 3 , or R 3 with R 4 , or R 4 with R 5 , form, together with the carbon atoms carrying them, an optionally substituted, mono- or bi-cyclic group optionally containing 1 or 2 hetero atoms, R 16 represents a hydrogen atom or an alkyl group, 7 represents an aryl, heteroaryl or aryl-alkyl group, its optical isomers, addition salts thereof with a pharmaceutically acceptable acid or base, and hydrates and solvates thereof.

  化合物的化学式（I）：其中：表示单键或双键，表示选自R9a、R9b、R9c的环系统，X和Y的定义如描述中所述，R1表示选自氢、芳基、杂环芳基、环烷基、可选择取代烷基和COR11的基团，其中R11的定义如描述中所述，R2至R8分别表示选自氢、卤素、羟基、多卤代烷基、硝基、可选择取代烷基、可选择取代氨基、可选择取代烷氧基、—OPO(OH)2的基团，其中m表示整数，使得1≤m<4，或R2与R3、或R3与R4、或R4与R5形成一个可选择取代的、含有1或2个杂原子的单环或双环基团，R16表示氢原子或烷基，表示芳基、杂环芳基或芳基烷基，其光学异构体，与药用可接受酸或碱形成的加合物盐，以及其水合物和溶剂合物。
• A Novel Photo-Induced Substitution of Alkyl 2-Cyano-3-quinolinecarboxylates
  作者：Isao Ono、Yoshiyuki Fujiki、Naoki Fujinami、Toshihiko Hoshi

  DOI：10.1246/cl.1989.371

  日期：1989.3

  Irradiation of 2-quinolinecarbonitriles having an alkoxycarbonyl group at the 3-position afforded five-membered and/or six-membered lactones in normal alcohols depending on their alkyl-chain-length, whereas the irradiation in 2-propanol and t-butyl alcohol did not cause any cyclization, but instead decynated and methylated products were obtained, respectively.

  辐照在 3 位上具有烷氧基羰基的 2-喹啉甲腈，根据其烷基链的长度，可在普通醇中得到五元和/或六元内酯，而在 2-丙醇和叔丁醇中辐照则不会导致任何环化，而是分别得到炔化和甲基化产物。
• A new method for the preparation of 2-hydroxymethyl-3-quinolinecarboxylic acid lactone derivatives.
  作者：TAKUSHI KURIHARA、TAKASHI MICHIDA、HIROSHI HIRANO

  DOI：10.1248/cpb.23.2451

  日期：——

  The reaction of 2-acetoxymethyl-3-acetylquinolines (V, VI) with sodium hydride gave 2-hydroxymethyl-3-quinolinecarboxylic acid lactones (IX, X), presumably formed with the migration of acetyl group. On the other hand, the fact that the reaction of 3-acetyl-2-benzoyloxymethylquinoline (VIII) with sodium hydride gave a lactone (IX) and acetophenone would strongly support for the mechanism of the lactone formation with the acyl migration.

  2-acetoxymethyl-3-acetylquinolines (V, VI) 与氢化钠反应生成 2-hydroxymethyl-3-quinolinecarboxylic acid lactones (IX, X)，推测是乙酰基迁移形成的。另一方面，3-乙酰基-2-苯甲酰氧基甲基喹啉（VIII）与氢化钠反应生成内酯（IX）和苯乙酮，这一事实有力地支持了酰基迁移形成内酯的机理。