tert-butyl 3-chloro-2-methyl-5-oxo-5H-spiro[furo[3,4-b]pyridine-7,4'-piperidine]-1'-carboxylate | 934361-44-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tert-butyl 3-chloro-2-methyl-5-oxo-5H-spiro[furo[3,4-b]pyridine-7,4'-piperidine]-1'-carboxylate
• 英文别名: 3-chloro-2-methyl-5H-spiro[furo[3,4-b]pyridine-7,4'-piperidin]-5-one；Tert-butyl 3-chloro-2-methyl-5-oxospiro[furo[3,4-b]pyridine-7,4'-piperidine]-1'-carboxylate
• CAS: 934361-44-1
• 化学式: C₁₇H₂₁ClN₂O₄
• 分子量: 352.818
• InChiKey: CQAIQJGDEQZPFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-chloro-2-methyl-5-oxo-5H-spiro[furo[3,4-b]pyridine-7,4'-piperidine]-1'-carboxylate 在 二异丁基氢化铝 、 甲醇 、 sodium hydroxide 、 水 作用下， 以 甲苯 为溶剂， 反应 2.33h， 生成 1,1-Dimethylethyl 3-chloro-5-hydroxy-2-methylspiro[furo[3,4-b]pyridine-7(5H),4a(2)-piperidine]-1a(2)-carboxylate
  参考文献：
  名称：

  [EN] ACYLATED SPIROPIPERIDINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR MODULATORS
  [FR] DERIVES SPIROPIPERIDINES ACYLES CONVENANT COMME MODULATEURS DES RECEPTEURS DE LA MELANOCORTINE-4

  摘要：

  公开号：

  WO2007041052A3
• 作为产物：
  描述：

  Tert-butyl 3-chloro-3'-iodo-2-methyl-5-oxospiro[furo[3,4-b]pyridine-7,4'-piperidine]-1'-carboxylate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以96.6%的产率得到tert-butyl 3-chloro-2-methyl-5-oxo-5H-spiro[furo[3,4-b]pyridine-7,4'-piperidine]-1'-carboxylate
  参考文献：
  名称：

  Preparation of 3,4-fused-spiro[furan-5(5H),4′-piperidin]-2-one

  摘要：

  A general method for the preparation of various 3,4-fused-spiro[furan-5(5H),4'-piperidini-2-one with high yield is reported. The formation of spiro[furarione-piperidine] structure was achieved by a Suzuki coupling, followed by an iodolactonization reaction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.035

文献信息

• A concise synthesis of 3,4-fused spiro[isobenzofuran-3-ones], spiro[furo[3,4- b ]pyridin-5(7 H )-ones], 3-aryl-, and alkylphthalides
  作者：Jeffrey T. Kuethe、Kevin M. Maloney

  DOI：10.1016/j.tet.2013.02.051

  日期：2013.6

  A synthetically useful protocol has been developed for the preparation of highly functionalized 3,4-fused spiro[isobenzofuran-3-ones], spiro[furo[3,4-b]pyridin-5(7H)-ones], 3-aryl-, and alkylphthalides. Reaction of 2-iodobenzoate esters and 2-iodopyridine carboxylate esters with i-PrMgCl center dot LiCl in the presence of cyclic ketones under standard Barbier reaction conditions affords 3,4-fused spiro[isobenzofuran-3-ones] and spiro[furo[3,4-b]pyridin-5(7H)-ones] in good to excellent yields. Step-wise addition of i-PrMgCl center dot LiCl to 2-iodobenzoate esters followed by trapping with various aldehydes yields 3-aryl and 3-alkylphthalides; whereas, under similar conditions access to 3-aryl and 3-alylazaphthalides is also possible. Extension of this methodology toward the preparation of 3-n-butylphthalide and chrycolide, a natural product isolated from the leaves and stems of Chrysanthemum coronarium, is also described. (C) 2013 Elsevier Ltd. All rights reserved.
• ACYLATED SPIROPIPERIDINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR MODULATORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP1940842B1

  公开（公告）日：2012-05-30
• Acylated Spiropiperidine Derivatives as Melanocortin-4 Receptor Modulators
  申请人：Jian Tianying

  公开号：US20090170863A1

  公开（公告）日：2009-07-02

  Certain novel N-acylated spiropiperidine derivatives are ligands of the human melanocortin receptor(s) and, in particular, are selective ligands of the human melanocortin-4 receptor (MC-4R). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of MC-4R, such as obesity, diabetes, nicotine addiction, alcoholism, sexual dysfunction, including erectile dysfunction and female sexual dysfunction.
• US8293900B2
  申请人：——

  公开号：US8293900B2

  公开（公告）日：2012-10-23
• [EN] ACYLATED SPIROPIPERIDINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR MODULATORS<br/>[FR] DERIVES SPIROPIPERIDINES ACYLES CONVENANT COMME MODULATEURS DES RECEPTEURS DE LA MELANOCORTINE-4
  申请人：MERCK & CO INC

  公开号：WO2007041052A3

  公开（公告）日：2007-05-31