2,3,8,8a-tetrahydroindolizin-7(1H)-one | 905717-35-3

• 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: 2,3,8,8a-tetrahydroindolizin-7(1H)-one
• 英文别名: 2,3,8,8a-tetrahydro-1H-indolizin-7-one
• CAS: 905717-35-3
• 化学式: C₈H₁₁NO
• 分子量: 137.181
• InChiKey: WHFCAIFZHMUWRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  238.5±20.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,8,8a-tetrahydroindolizin-7(1H)-one 在 4',5'-dimethoxy-1,1':2',1''-terphenyl 、 叔丁基锂 、 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 9.42h， 生成 7-(4,5-dimethoxy-[1,1'-biphenyl]-2-yl)-1,2,3,5,8,8a-hexahydroindolizine
  参考文献：
  名称：

  Synthesis of Tylocrebrine and Related Phenanthroindolizidines by VOF₃-Mediated Oxidative Aryl-Alkene Coupling

  摘要：

  A highly convergent strategy to prepare phenanthroindolizidines is reported involving three consecutive C-C coupling reactions. This sequence features a novel VOF3-mediated aryl-alkene coupling in the final step, which enables regioselective preparation of C5-substituted phenanthroindolizidines for the first time. This strategy has been applied to the synthesis of eight natural and unnatural members in this class to investigate the scope of this chemistry and to explore structure-activity relationships.

  DOI：

  10.1021/ol1023954
• 作为产物：
  描述：

  1-Boc-2-吡咯烷乙酸 在 N-甲基吗啉 、 盐酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 2,3,8,8a-tetrahydroindolizin-7(1H)-one
  参考文献：
  名称：

  Amino Acid-Derived Enaminones:  A Study in Ring Formation Providing Valuable Asymmetric Synthons

  摘要：

  A new reaction for the preparation of enaminones has been discovered. This method employs beta-amino acids as starting materials to allow diversification as well as incorporation of chirality. The beta-amino acids, once converted to ynones, are readily cyclized to the desired six-membered enaminone via a two-step, one-pot protocol. Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond making and bond breaking, thus changing the mode of addition.

  DOI：

  10.1021/ja0609046

文献信息

• [EN] (--)- HUPERZINE A PROCESSES AND RELATED COMPOSITIONS AND METHODS OF TREATMENT<br/>[FR] PROCÉDÉS DE FABRICATION DE (-) HUPERZINE A, COMPOSITIONS ASSOCIÉES, ET MÉTHODES DE TRAITEMENT
  申请人：UNIV YALE

  公开号：WO2012121863A1

  公开（公告）日：2012-09-13

  The invention provides (1) processes for making substantially-pure (-) huperzine A and substantially-pure (-) huperzine A derivatives; (2) compositions useful in making substantially-pure (-) huperzine A and substantially-pure (-) huperzine A derivatives; and (3) methods of treating or preventing neurological disorders using substantially-pure (-) huperzine A and substantially-pure (-) huperzine A derivatives.

  该发明提供了三个方面：(1) 制备几乎纯的(-)华佩嗪A和几乎纯的(-)华佩嗪A衍生物的过程；(2) 用于制备几乎纯的(-)华佩嗪A和几乎纯的(-)华佩嗪A衍生物的组合物；以及(3) 使用几乎纯的(-)华佩嗪A和几乎纯的(-)华佩嗪A衍生物治疗或预防神经系统疾病的方法。
• Copper-Assisted Palladium(II)-Catalyzed Direct Arylation of Cyclic Enaminones with Arylboronic Acids
  作者：Yong Wook Kim、Micah J. Niphakis、Gunda I. Georg

  DOI：10.1021/jo301531k

  日期：2012.11.2

  Described herein is a palladium(II)-catalyzed direct arylation of cyclic enaminones with arylboronic acids. The versatility of this method is that both electron-rich and electron-poor boronic acids can be coupled in high yields. A mixture of two Cu(II) additives was crucial for efficient cross-coupling. The role of each Cu(II) reagent appears to be distinct and complementary serving to assist catalyst

  本文描述的是钯(II)-催化的环状烯胺酮与芳基硼酸的直接芳基化。这种方法的多功能性在于富电子和缺电子硼酸都可以高产率耦合。两种 Cu(II) 添加剂的混合物对于有效的交叉耦合至关重要。每个 Cu(II) 试剂的作用似乎是不同的和互补的，有助于通过假定的芳基铜中间体帮助催化剂再氧化和金属转移。
• Rab7 GTPase Inhibitors and Related Methods of Treatment
  申请人：Wandinger-Ness Angela

  公开号：US20140248268A1

  公开（公告）日：2014-09-04

  This invention relates to compounds and their use as inhibitors or activators of Rab7 GTPase to treat or prevent the onset of Rab 7 GTPase-associated disorders such as neuropathies, cancer, metabolic diseases of bone and lipid storage. The invention is also applicable to infectious diseases where Rab7 is inactivated or its protein-protein interactions are modulated to facilitate intracellular survival of pathogens. The compound described acts as a competitive inhibitor of nucleotide binding and as such also has utility as a scaffold for targeting other small GTPases. In one aspect, methods of treatment of the invention are used to treat or prevent the onset of hereditary sensory neuropathies such as Charcot-Marie-Tooth type 2B disease. Related pharmaceutical compositions, assays, and drug screens are also provided.

  本发明涉及化合物及其作为Rab7 GTP酶抑制剂或激活剂的用途，以治疗或预防Rab 7 GTP酶相关疾病，如神经病变、癌症、骨代谢疾病和脂质储存病。该发明还适用于Rab7被失活或其蛋白质-蛋白质相互作用被调节以促进病原体的细胞内生存的感染性疾病。所述化合物作为核苷酸结合的竞争性抑制剂，并且也具有作为靶向其他小GTP酶的支架的效用。在一个方面，本发明的治疗方法用于治疗或预防遗传性感觉神经病变，如Charcot-Marie-Tooth 2B病。还提供相关的制药组合物、测定和药物筛选。
• INTERMEDIATE COMPOUNDS UTILIZABLE IN SYNTHESIS OF (-) HUPERZINE AND PROCESS FOR OBTAIN ONE OF THESE INTERMEDIATE COMPOUNDS
  申请人：Yale University

  公开号：EP3434669A1

  公开（公告）日：2019-01-30

  The invention provides Intermediate compounds utilizable in synthesis of (-)-Huperzine and process for obtain one of these intermediate compounds.

  本发明提供了可用于合成 (-)-Huperzine 的中间体化合物以及获得这些中间体化合物之一的工艺。
• (−)-Huperzine A processes and related compositions and methods of treatment
  申请人：Herzon Seth

  公开号：US10059672B2

  公开（公告）日：2018-08-28

  The invention provides (1) processes for making substantially-pure (−) huperzine A and substantially-pure (−) huperzine A derivatives; (2) compositions useful in making substantially-pure (−) huperzine A and substantially-pure (−) huperzine A derivatives; and (3) methods of treating or preventing neurological disorders using substantially-pure (−) huperzine A and substantially-pure (−) huperzine A derivatives.

  本发明提供了（1）制造实质上纯净的（-）虎佩嗪 A 和实质上纯净的（-）虎佩嗪 A 衍生物的工艺；（2）用于制造实质上纯净的（-）虎佩嗪 A 和实质上纯净的（-）虎佩嗪 A 衍生物的组合物；以及（3）使用实质上纯净的（-）虎佩嗪 A 和实质上纯净的（-）虎佩嗪 A 衍生物治疗或预防神经系统疾病的方法。