ethyl 2',4-dioxospiro[cyclohexane-1,3’-indoline]-1‘-carboxylate

• 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: ethyl 2',4-dioxospiro[cyclohexane-1,3’-indoline]-1‘-carboxylate
• 英文别名: ethyl 2',4-dioxospiro[cyclohexane-1,3'-indoline]-1'-carboxylate；Ethyl 2',4-dioxospiro[cyclohexane-1,3'-indole]-1'-carboxylate
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: SDXAYYVWXAGWGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2',4-dioxospiro[cyclohexane-1,3’-indoline]-1‘-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以88%的产率得到spiro[cyclohexane-1,3’-indoline]-2’,4-dione
  参考文献：
  名称：

  A new synthetic procedure to spiro[cyclohexane-1,3′-indoline]-2′,4-diones

  摘要：

  A new synthetic pathway to spiro[cyclohexane-1,3'-indoline]-2',4-diones was found starting from 3-chloromethylene-2-indolones 1 and Danishefsky's diene 2. Their synthesis consists of several steps involving the formation of the cycloadducts, the 6-chloro-4-trimethylsilyloxy-2-methoxyspiro[cyclohex-3-en-1,3'-indolin]-2'-one derivatives, transformed into spiro[cyclohexa-2,5-dienl,3'-indoline]-2',4-diones via 6-chloro-spiro[cyclohex-2-en-1,3'-indoline]-2',4-dione intermediates. The reduction of spiro[cyclohexa-2,5-dien-1,3'-indoline]-2',4-diones gave spiro[cyclohexane-1,3'-indoline]-2',4-diones 7. Using a 'one pot reaction', starting from 1 and 2, compounds 7 were obtained in satisfactory overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00627-6
• 作为产物：
  描述：

  ethyl 2',4-dioxospiro[cyclohex-2-ene-1,3'-indoline]-1'-carboxylate 在 10% palladium on carbon 、 氢气 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以17.3 g的产率得到ethyl 2',4-dioxospiro[cyclohexane-1,3’-indoline]-1‘-carboxylate
  参考文献：
  名称：

  C -3a-（3-羟丙基）四氢吡咯并[2,3- b ]吲哚和C -4a-（2-氨基乙基）-四氢吡喃并[2,3- b ]吲哚衍生物的化学选择不对称合成

  摘要：

  新的四氢吡咯并[2,3- b ]吲哚19和四氢吡喃并[2,3- b ]吲哚20环的不对称合成，分别在C-3a和C-4a位被羟基和氨基官能化的链取代，从外消旋螺[环己烷-1,3'-二氢吲哚] -2'，4-二酮7开始。制备了通过不对称扩环从（±）-7获得的对映体螺氧基-氮杂叠氮吲哚酮（+）- 10和通过水解10得到的氨基酸（+）- 14作为关键中间体用于合成对映纯化合物（-）- 19和（-）-20。由于氨基酸14是化学衍生物制备衍生物19和20的常用中间体，因此进行了实验和计算研究，以选择性地获得这些化合物并为其形成提供机理上的合理化。

  DOI：

  10.1016/j.tet.2009.01.004

文献信息

• PHARMACEUTICAL COMPOUNDS
  申请人：Heptares Therapeutics Limited

  公开号：US20180105491A1

  公开（公告）日：2018-04-19

  This invention relates to compounds that are agonists of the muscarinic M 1 receptor or M 1 and M 4 receptors and which are useful in the treatment of muscarinic M 1 or M 1 /M 4 receptor mediated diseases. Also provided are pharmaceutical compositions containing the compounds and the therapeutic uses of the compounds. Compounds provided are of formula wherein Q 4 , Q 5 , R 5 , p, V, Q 1 , Q 2 , X 1 , X 2 and W are defined herein.

  这项发明涉及激动毒蕈碱M1受体或M1和M4受体的化合物，这些化合物在治疗毒蕈碱M1或M1/M4受体介导的疾病中有用。还提供了含有这些化合物的药物组合物以及这些化合物的治疗用途。所提供的化合物的公式如下：其中Q4、Q5、R5、p、V、Q1、Q2、X1、X2和W在此处被定义。
• Substituted cyclohexanes as muscarinic M1 receptor and/or M4 receptor agonists
  申请人：Heptares Therapeutics Limited

  公开号：US10259787B2

  公开（公告）日：2019-04-16

  This invention relates to compounds that are agonists of the muscarinic M1 receptor or M1 and M4 receptors and which are useful in the treatment of muscarinic M1 or M1/M4 receptor mediated diseases. Also provided are pharmaceutical compositions containing the compounds and the therapeutic uses of the compounds. Compounds provided are of formula wherein Q4, Q5, R5, p, V, Q1, Q2, X1, X2 and W are defined herein.

  本发明涉及毒蕈碱类 M1 受体或 M1 和 M4 受体的激动剂，可用于治疗毒蕈碱类 M1 或 M1/M4 受体介导的疾病。此外，还提供了含有这些化合物的药物组合物以及这些化合物的治疗用途。所提供的化合物为式 其中 Q4、Q5、R5、p、V、Q1、Q2、X1、X2 和 W 在此定义。
• Substituted spirocyclohexanes as muscarinic M1 receptor and/or M4 receptor agonists
  申请人：Heptares Therapeutics Limited

  公开号：US10759751B2

  公开（公告）日：2020-09-01

  This invention relates to compounds that are agonists of the muscarinic M1 receptor or M1 and M4 receptors and which are useful in the treatment of muscarinic M1 or M1/M4 receptor mediated diseases. Also provided are pharmaceutical compositions containing the compounds and the therapeutic uses of the compounds. Compounds provided are of formula wherein Q4, Q5, R5, p, V, Q1, Q2, X1, X2 and W are defined herein.

  本发明涉及毒蕈碱类 M1 受体或 M1 和 M4 受体的激动剂，可用于治疗毒蕈碱类 M1 或 M1/M4 受体介导的疾病。此外，还提供了含有这些化合物的药物组合物以及这些化合物的治疗用途。所提供的化合物为式 其中 Q4、Q5、R5、p、V、Q1、Q2、X1、X2 和 W 在此定义。
• HETEROCYCLIC COMPOUNDS HAVING ACTIVITY AS MODULATORS OF MUSCARINIC M1 AND/OR M4 RECEPTORS IN THE TREATMENT OF CNS DISEASES AND PAINS.
  申请人：Heptares Therapeutics Limited

  公开号：EP3526207B1

  公开（公告）日：2021-09-08
• SUBSTITUTED CYCLOHEXANES AS MUSCARINIC M1 RECEPTOR AND/OR M4 RECEPTOR AGONISTS
  申请人：Heptares Therapeutics Limited

  公开号：US20190202783A1

  公开（公告）日：2019-07-04

  This invention relates to compounds that are agonists of the muscarinic M 1 receptor or M 1 and M 4 receptors and which are useful in the treatment of muscarinic M 1 or M 1 /M 4 receptor mediated diseases. Also provided are pharmaceutical compositions containing the compounds and the therapeutic uses of the compounds. Compounds provided are of formula wherein Q 4 , Q 5 , R 5 , p, V, Q 1 , Q 2 , X 1 , X 2 and W are defined herein.