1'-benzyl-5-methyl-4,5-dihydro-3H-spiro[1,5-benzoxazepine-2,4'-piperidine] | 1298034-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1'-benzyl-5-methyl-4,5-dihydro-3H-spiro[1,5-benzoxazepine-2,4'-piperidine]
• 英文别名: 1'-Benzyl-5-methylspiro[3,4-dihydro-1,5-benzoxazepine-2,4'-piperidine]
• CAS: 1298034-42-0
• 化学式: C₂₁H₂₆N₂O
• 分子量: 322.45
• InChiKey: SCOQLAHYESKJCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1'-benzyl-5-methyl-4,5-dihydro-3H-spiro[1,5-benzoxazepine-2,4'-piperidine] 在 盐酸 、 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以68%的产率得到5-methyl-4,5-dihydro-3H-spiro[1,5-benzoxazepine-2,4'-piperidine] hydrochloride
  参考文献：
  名称：

  Discovery of novel SCD1 inhibitors: 5-Alkyl-4,5-dihydro-3H-spiro[1,5-benzoxazepine-2,4′-piperidine] analogs

  摘要：

  Expansion of the 6-membered ring and subsequent fine-tuning of the newly obtained 7-membered spiropiperidine structure resulted in the discovery of a series of novel and potent SCD1 inhibitors. Preliminary SAR was explored by modifying an alkyl chain on the azepine nitrogen and resulted in the identification of a highly potent SCD1 inhibitor: 6-[5-(cyclopropylmethyl)-4,5-dihydro-1'H,3H-spiro[1,5-benzoxazepine-2,4'-piperidin]-1'-yl]-N-(2-hydroxy-2-pyridin-3-ylethyl)pyridazine-3-carboxamide (9). Compound 9 exhibited an IC50 value of 0.01 mu M against human SCD1. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.002
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 四氢吡咯 、 吡啶 、 盐酸羟胺 、 二异丁基氢化铝 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 44.33h， 生成 1'-benzyl-5-methyl-4,5-dihydro-3H-spiro[1,5-benzoxazepine-2,4'-piperidine]
  参考文献：
  名称：

  Discovery of novel SCD1 inhibitors: 5-Alkyl-4,5-dihydro-3H-spiro[1,5-benzoxazepine-2,4′-piperidine] analogs

  摘要：

  Expansion of the 6-membered ring and subsequent fine-tuning of the newly obtained 7-membered spiropiperidine structure resulted in the discovery of a series of novel and potent SCD1 inhibitors. Preliminary SAR was explored by modifying an alkyl chain on the azepine nitrogen and resulted in the identification of a highly potent SCD1 inhibitor: 6-[5-(cyclopropylmethyl)-4,5-dihydro-1'H,3H-spiro[1,5-benzoxazepine-2,4'-piperidin]-1'-yl]-N-(2-hydroxy-2-pyridin-3-ylethyl)pyridazine-3-carboxamide (9). Compound 9 exhibited an IC50 value of 0.01 mu M against human SCD1. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.002

文献信息

• Discovery of novel SCD1 inhibitors: 5-Alkyl-4,5-dihydro-3H-spiro[1,5-benzoxazepine-2,4′-piperidine] analogs
  作者：Yoshikazu Uto、Yuko Ueno、Yohei Kiyotsuka、Yuriko Miyazawa、Hitoshi Kurata、Tsuneaki Ogata、Toshiyuki Takagi、Satoko Wakimoto、Jun Ohsumi

  DOI：10.1016/j.ejmech.2011.02.002

  日期：2011.5

  Expansion of the 6-membered ring and subsequent fine-tuning of the newly obtained 7-membered spiropiperidine structure resulted in the discovery of a series of novel and potent SCD1 inhibitors. Preliminary SAR was explored by modifying an alkyl chain on the azepine nitrogen and resulted in the identification of a highly potent SCD1 inhibitor: 6-[5-(cyclopropylmethyl)-4,5-dihydro-1'H,3H-spiro[1,5-benzoxazepine-2,4'-piperidin]-1'-yl]-N-(2-hydroxy-2-pyridin-3-ylethyl)pyridazine-3-carboxamide (9). Compound 9 exhibited an IC50 value of 0.01 mu M against human SCD1. (C) 2011 Elsevier Masson SAS. All rights reserved.