7-methylbicyclo[4.2.0]octa-1,3,5-trien-7-amine | 1128111-84-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 7-methylbicyclo[4.2.0]octa-1,3,5-trien-7-amine
• CAS: 1128111-84-1
• 化学式: C₉H₁₁N
• mdl: MFCD19215440
• 分子量: 133.193
• InChiKey: PGQILBLSHQORKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-methylbicyclo[4.2.0]octa-1,3,5-trien-7-amine 、 苯甲醛 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 生成 7-methyl-N-[(1E)-phenylmethylene]bicyclo[4.2.0]octa-1,3,5-trien-7-amine
  参考文献：
  名称：

  用C（sp3）合成3,4-二氢异喹啉？H活化/电环化策略：Coralydine的全合成

  摘要：

  多亏了CH活化：溴苯（1）通过包括C（sp 3）H活化，Curtius重排和串联电环的序列合成了3-芳基-3,4-二氢异喹啉（2）开/6π电环化。该方法适用于各种含异喹啉的分子的合成，包括四氢小ber碱生物碱珊瑚素。

  DOI：

  10.1002/anie.200804444
• 作为产物：
  描述：

  7-Isocyanato-7-methylbicyclo[4.2.0]octa-1,3,5-triene 在 盐酸 、 水 作用下， 以 甲苯 为溶剂， 以1.09 g的产率得到7-methylbicyclo[4.2.0]octa-1,3,5-trien-7-amine
  参考文献：
  名称：

  用C（sp3）合成3,4-二氢异喹啉？H活化/电环化策略：Coralydine的全合成

  摘要：

  多亏了CH活化：溴苯（1）通过包括C（sp 3）H活化，Curtius重排和串联电环的序列合成了3-芳基-3,4-二氢异喹啉（2）开/6π电环化。该方法适用于各种含异喹啉的分子的合成，包括四氢小ber碱生物碱珊瑚素。

  DOI：

  10.1002/anie.200804444

文献信息

• Discovery of Amino-cyclobutarene-derived Indoleamine-2,3-dioxygenase 1 (IDO1) Inhibitors for Cancer Immunotherapy
  作者：Hongjun Zhang、Kun Liu、Qinglin Pu、Abdelghani Achab、Michael J. Ardolino、Mangeng Cheng、Yongqi Deng、Amy C. Doty、Heidi Ferguson、Xavier Fradera、Ian Knemeyer、Ravi Kurukulasuriya、Yu-hong Lam、Charles A. Lesburg、Theodore A. Martinot、Meredeth A. McGowan、J. Richard Miller、Karin Otte、Purakattle J. Biju、Nunzio Sciammetta、Nicolas Solban、Wensheng Yu、Hua Zhou、Xiao Wang、David Jonathan Bennett、Yongxin Han

  DOI：10.1021/acsmedchemlett.9b00344

  日期：2019.11.14

  Checkpoint inhibitors have demonstrated unprecedented efficacy and are evolving to become standard of care for certain types of cancers. However, low overall response rates often hamper the broad utility and potential of these breakthrough therapies. Combination therapy strategies are currently under intensive investigation in the clinic, including the combination of PD-1/PD-L1 agents with IDO1 inhibitors. Here, we report the discovery of a class of IDO1 heme-binding inhibitors featuring a unique amino-cyclobutarene motif, which was discovered through SBDD from a known and weakly active inhibitor. Subsequent optimization efforts focused on improving metabolic stability and were greatly accelerated by utilizing a robust SNAr reaction of a facile nitro-furazan intermediate to quickly explore different polar side chains. As a culmination of these efforts, compound 16 was identified and demonstrated a favorable overall profile with superior potency and selectivity. Extensive studies confirmed the chemical stability and drug-like properties of compound 16, rendering it a potential drug candidate.
• Synthesis of 3,4-Dihydroisoquinolines by a C(sp³)H Activation/Electrocyclization Strategy: Total Synthesis of Coralydine
  作者：Manon Chaumontet、Riccardo Piccardi、Olivier Baudoin

  DOI：10.1002/anie.200804444

  日期：2009.1

  Thanks to CH activation: 3‐Aryl‐3,4‐dihydroisoquinolines (2) are synthesized from bromobenzenes (1) by a sequence comprising a C(sp3)H activation, a Curtius rearrangement, and a tandem electrocyclic ring‐opening/6π electrocyclization. This method is applied to the synthesis of various isoquinoline‐containing molecules, including the tetrahydroprotoberberine alkaloid coralydine.

  多亏了CH活化：溴苯（1）通过包括C（sp 3）H活化，Curtius重排和串联电环的序列合成了3-芳基-3,4-二氢异喹啉（2）开/6π电环化。该方法适用于各种含异喹啉的分子的合成，包括四氢小ber碱生物碱珊瑚素。