3,4,10,10a-tetrahydro-1H-[1,4]oxazino[4,3-a]indole | 1160487-69-3

• 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: 3,4,10,10a-tetrahydro-1H-[1,4]oxazino[4,3-a]indole
• CAS: 1160487-69-3
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: YSGXYHQZFPFOQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  反应 0.17h， 生成 3,4,10,10a-tetrahydro-1H-[1,4]oxazino[4,3-a]indole
  参考文献：
  名称：

  Novel, Versatile Three-Step Synthesis of 1,2,3,4,10,10a-Hexahydro­pyrazino[1,2-a]indoles by Intramolecular Carbene-Mediated C-H Insertion

  摘要：

  开发了一种新的便捷三步合成特权中枢神经系统骨架1,2,3,4,10,10a-六氢吡嗪并[1,2-a]吲哚的方法。该方法利用了由2-氟苯醛制得的苯基哌嗪衍生的托磺酰肼中发生的分子内碳烯介导的C-H插入。值得注意的是，哌嗪可以被其他环状氮碱替代，该方法成功扩展到了吡咯烷、哌啶、七元环胺、吗啉和同哌嗪。

  DOI：

  10.1055/s-0030-1258967

文献信息

• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。
• Alicyclic‐Amine‐Derived Imine‐BF₃ Complexes: Easy‐to‐Make Building Blocks for the Synthesis of Valuable α‐Functionalized Azacycles
  作者：Subhradeep Dutta、Jae Hyun Kim、Kamal Bhatt、Dillon R. L. Rickertsen、Khalil A. Abboud、Ion Ghiviriga、Daniel Seidel

  DOI：10.1002/anie.202313247

  日期：2024.1.2

  A new strategy to access α‐functionalized alicyclic amines via their corresponding imine‐BF₃ complexes is reported. Isolable imine‐BF₃ complexes, readily prepared via dehydrohalogenation of N‐bromoamines in a base‐promoted/18‐crown‐6 catalyzed process followed by addition of boron trifluoride etherate, undergo reactions with a wide range of organometallic nucleophiles to afford α‐functionalized azacycles. Organozinc and organomagnesium nucleophiles add at ambient temperatures, obviating the need for cryogenic conditions. In situ preparation of imine‐BF₃ complexes provides access to α‐functionalized morpholines and piperazines directly from their parent amines in a single operation. α‐Functionalized morpholines can be elaborated further, for instance by installing a second substituent in the α′‐position.

  摘要 报告了一种通过相应的亚胺-BF3 复合物获得α-官能化脂环胺的新策略。可分离的亚胺- 配合物在碱促进/18-冠-6 催化过程中通过 N-溴胺的脱氢卤化，然后加入三氟化硼醚化物而容易制备。有机锌和有机镁亲核物在常温下添加，无需低温条件。在原位制备亚胺- 复合物的过程中，只需一次操作就能直接从母胺制备出 α-官能化吗啉和哌嗪。α-官能化吗啉还可以进一步制备，例如在 α′ 位上安装第二个取代基。