ethyl 1,2-dihydro-3H-pyrrolizine-7-carboxylate | 34951-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯嗪
• 英文名称: ethyl 1,2-dihydro-3H-pyrrolizine-7-carboxylate
• 英文别名: Ethyl 1,2-dihydro-3H-pyrrolo<1,2-a>pyrrole-7-carboxylate；2,3-Dihydro-1H-pyrrolizin-7-carbonsaeure-ethylester；ethyl 2,3-dihydro-1H-pyrrolizine-7-carboxylate；7-Ethoxycarbonyl-1,2-dihydro-3H-pyrrolizin；6,7-dihydro-5H-pyrrolizine-1-carboxylic acid ethyl ester；ethyl 6,7-dihydro-5H-pyrrolizine-1-carboxylate
• CAS: 34951-59-2
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: QNFBJKVNVWKMNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 1,2-dihydro-3H-pyrrolizine-7-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以83%的产率得到2,3-二氢-1H-吡咯里嗪-7-甲醇
  参考文献：
  名称：

  Roeder, Erhard; Wiedenfeld, Helmut; Bourauel, Thomas, Liebigs Annalen der Chemie, 1986, # 9, p. 1645 - 1647

  摘要：

  DOI：
• 作为产物：
  描述：

  乙基 1H-吡咯-3-羧酸 在 氢氧化钾 、 双氧水 、 iron(II) sulfate 、 sodium iodide 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 7.17h， 生成 ethyl 1,2-dihydro-3H-pyrrolizine-7-carboxylate
  参考文献：
  名称：

  Oxidative Radical Cyclization of (.omega.-Iodoalkyl)indoles and Pyrroles. Synthesis of (-)-Monomorine and Three Diastereomers

  摘要：

  Addition of excess hydrogen peroxide (10 equiv) to a sonicated solution of FeSO4:7H(2)O (1 equiv) in Dh ISO containing the N-(omega-iodoalkyl)indoles 4, 5, 11, and 13 effected oxidative radical cyclization to 6, 7, 14, and 15, respectively. The (omega-iodoalkyl)pyrroles 21, 22, 27, 38, and 49 underwent analogous cyclization reactions to 23, 24, 28, 39, and 50, respectively. The regiochemistry of these radical cyclization reactions was correctly predicted by FMO calculations in all cases but one. For compound 38, FMO calculations indicated that radical attack should take place at both C-3 and C-5. Only the product of cyclization at C-5, i.e., 39, was observed. The enantiomerically pure bicyclic ketone 42, prepared by the above technique from the iodide 53, was converted into 55 which, on catalytic reduction (H-2/Rh-A1(2)O(3)), gave a mixture of (-)-monomorine (40) and three of its diastereomers 56-58 (see, however, Note Added in Proof).

  DOI：

  10.1021/jo00088a029

文献信息

• Synthesis of 2,3-Dihydropyrrolizines from Weinreb 3-(Pyrrolidin-2-ylidene­)propionamides or Weinreb<i>N-</i>Vinylprolinamides
  作者：Alfonso González-Ortega、Luis Calvo、M. Carmen Sañudo

  DOI：10.1055/s-2002-35220

  日期：——

  Weinreb 3-(pyrrolidin-2-ylidene)propionamides and Weinreb N-vinylprolinamides were used for the synthesis of 2,3-dihydropyrrolizines. The selective reaction of the carboxamide group with organometallic compounds allowed us to obtain a great variety of carbonyl intermediates, analogous to the Hantzsch and Knorr pyrrole synthesis, which were thermally cyclized.

  Weinreb 3-(吡咯烷-2-亚基)丙酰胺和Weinreb N-乙烯基脯氨酰胺被用于合成2,3-二氢吡咯嗪。羧酰胺基团与有机金属化合物的选择性反应使我们能够获得多种类似于Hantzsch和Knorr吡咯合成中的羰基中间体，这些中间体在热力作用下环化。
• HEPATITIS B CAPSID ASSEMBLY MODULATORS
  申请人：VenatoRx Pharmaceuticals, Inc.

  公开号：US20190375708A1

  公开（公告）日：2019-12-12

  Described herein are hepatitis B capsid assembly modulators and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for the treatment of hepatitis B.

  本文描述了乙型肝炎胶囊组装调节剂和包含该类化合物的药物组合物。这些化合物和组合物对于治疗乙型肝炎是有用的。
• Synthesis of fused pyrrolines by the intramolecular cycloadition of azides application to the pyrrolizidine alkaloids.
  作者：William H. Pearson

  DOI：10.1016/s0040-4039(00)89182-0

  日期：1985.1

  Intramolecular 1,3-dipolar cycloaddition of azide 4 proceeds through triazoline 5 and vinyl aziridine 6, resulting in the formation of the 1,5-homodienyl shift product 7 and the tetrahydropyrrolizines 8 and 9. Compound 8 represents a formal total synthesis of supinidine.

  叠氮化物4的分子内1，3-偶极环加成通过三唑啉5和乙烯基氮丙啶6进行，导致形成1，5-同二烯基移位产物7和四氢吡咯烷酮8和9。化合物8代表了泛素的正式全合成。
• Hepatitis B capsid assembly modulators
  申请人：VenatoRx Pharmaceuticals, Inc.

  公开号：US10590076B2

  公开（公告）日：2020-03-17

  Described herein are hepatitis B capsid assembly modulators and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for the treatment of hepatitis B.

  本文描述的是乙型肝炎囊壳组装调节剂和包含所述化合物的药物组合物。 所述化合物和组合物可用于治疗乙型肝炎。
• [EN] CAPSID PROTEIN ASSEMBLY INHIBITOR CONTAINING PYRROLO HETEROCYCLE<br/>[FR] PYRROLO-HÉTÉROCYCLE CONTENANT UN INHIBITEUR D'ASSEMBLAGE DE PROTÉINES CAPSIDIQUES<br/>[ZH] 含有吡咯并杂环的衣壳蛋白装配抑制剂
  申请人：CHIA TAI TIANQING PHARMACEUTICAL GROUP CO LTD

  公开号：WO2020156494A1

  公开（公告）日：2020-08-06

  本申请属于药物化学领域，涉及一种含有吡咯并杂环的衣壳蛋白装配抑制剂，具体而言，涉及式I所示的化合物、其立体异构体或其药学上可接受的盐、其制备方法、药物组合物及医药用途，包括用于治疗受益于衣壳蛋白装配抑制的疾病的用途，尤其是乙型肝炎病毒感染引起的疾病。