(R)-(N-benzyloxycarbonyl)-2-(2-oxoethyl)pyrrolidine | 1036404-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-(N-benzyloxycarbonyl)-2-(2-oxoethyl)pyrrolidine
• 英文别名: (R)-benzyl 2-(2-oxoethyl)pyrrolidine-1-carboxylate；benzyl 2-(2-oxoethyl)pyrrolidine-1-carboxylate；Phenylmethyl (2R)-2-(2-oxoethyl)-1-pyrrolidinecarboxylate；benzyl (2R)-2-(2-oxoethyl)pyrrolidine-1-carboxylate
• CAS: 1036404-01-9
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: RONFJKMOSBPPKV-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(N-benzyloxycarbonyl)-2-(2-oxoethyl)pyrrolidine 在 盐酸 、 titanium(IV) tetraethanolate 、 indium 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 60.0 ℃ 、405.33 kPa 条件下， 反应 23.0h， 生成 (+)-tetraponerine-1
  参考文献：
  名称：

  Natural Tetraponerines: A General Synthesis and Antiproliferative Activity

  摘要：

  A stereocontrolled general methodology to access all natural tetraponerines from (+)-T1 to (+)-T8 is detailed. Two consecutive indium-mediated aminoallylations with the appropriate enantiomer of chiral N-tert-butylsulfinamide and a thermodynamic control at the aminal stereocenter allow the formation of each natural tetraponerine with excellent stereoselectivity. The use of 4-bromobutanal in the first aminoallylation leads to the formation of 5-6-5 tetraponerines, while 5-bromopentanal is required to build the scaffold of 6-6-5 tetraponerines. A cross-metathesis reaction of the second aminoallylation product with cis-3-hexene is used to elongate the side chain up to 5 carbons so as to prepare the tetraponerines T5 to T8. The anticancer activity of these heavier tetraponerines against four different carcinoma human cell lines is examined, observing a promising cytotcodc activity of (+)-T7 against breast carcinoma cell line MCF-7.

  DOI：

  10.1021/jo500446f
• 作为产物：
  描述：

  (2R,Rs)-2-allyl-(N-tert-butylsulfinyl)pyrrolidine 在 2,6-二甲基吡啶 、 盐酸 、 sodium periodate 、 四氧化锇 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 反应 6.58h， 生成 (R)-(N-benzyloxycarbonyl)-2-(2-oxoethyl)pyrrolidine
  参考文献：
  名称：

  Natural Tetraponerines: A General Synthesis and Antiproliferative Activity

  摘要：

  A stereocontrolled general methodology to access all natural tetraponerines from (+)-T1 to (+)-T8 is detailed. Two consecutive indium-mediated aminoallylations with the appropriate enantiomer of chiral N-tert-butylsulfinamide and a thermodynamic control at the aminal stereocenter allow the formation of each natural tetraponerine with excellent stereoselectivity. The use of 4-bromobutanal in the first aminoallylation leads to the formation of 5-6-5 tetraponerines, while 5-bromopentanal is required to build the scaffold of 6-6-5 tetraponerines. A cross-metathesis reaction of the second aminoallylation product with cis-3-hexene is used to elongate the side chain up to 5 carbons so as to prepare the tetraponerines T5 to T8. The anticancer activity of these heavier tetraponerines against four different carcinoma human cell lines is examined, observing a promising cytotcodc activity of (+)-T7 against breast carcinoma cell line MCF-7.

  DOI：

  10.1021/jo500446f

文献信息

• [EN] FUMAGILLOL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES FUMAGILLOL, ET PROCÉDÉS CORRESPONDANTS DE FABRICATION ET D'UTILISATION
  申请人：ZAFGEN INC

  公开号：WO2017027684A1

  公开（公告）日：2017-02-16

  Disclosed herein, in part, are fumagillol compounds and methods of use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making fumagillol compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

  本文披露了富马吉醇化合物及其在治疗医学疾病（如肥胖症）中的用途方法。提供了富马吉醇化合物的药物组合物和制备方法。这些化合物被认为具有对蛋氨酸氨肽酶2的活性。
• Improved Protocol for Asymmetric, Intramolecular Heteroatom Michael Addition Using Organocatalysis: Enantioselective Syntheses of Homoproline, Pelletierine, and Homopipecolic Acid
  作者：Erik C. Carlson、Lauren K. Rathbone、Hua Yang、Nathan D. Collett、Rich G. Carter

  DOI：10.1021/jo800749t

  日期：2008.7.1

  indoline, and piperidine rings using an organocatalyzed, intramolecular heteroatom Michael addition is described. Application to the enantioselective synthesis of homoproline, homopipecolic acid, and pelletierine has been accomplished.

  描述了使用有机催化的分子内杂原子迈克尔加成构建对映体富集的吡咯烷、二氢吲哚和哌啶环的改进方案。已完成对高脯氨酸、高哌可酸和匹莱林的对映选择性合成的应用。
• Catalytic Asymmetric Additions of Enol Silanes to In Situ Generated Cyclic, Aliphatic <i>N</i> ‐Acyliminium Ions
  作者：Oleg Grossmann、Rajat Maji、Miles H. Aukland、Sunggi Lee、Benjamin List

  DOI：10.1002/anie.202115036

  日期：2022.2.21

  Saturated nitrogen heterocycles are essential pharmacophores in drugs and natural products, and general methods for their enantioselective synthesis are still highly sought after. A new direct approach utilizing hemiaminal methyl ethers as N-acyliminium precursors for the enantioselective preparation of cyclic, aliphatic and 2-subsituted pyrrolidines, piperidines and azepanes has been achieved.

  饱和氮杂环是药物和天然产物中重要的药效基团，其对映选择性合成的通用方法仍然备受追捧。一种新的直接方法利用半缩醛胺甲基醚作为N-酰亚胺前体，用于对映选择性制备环状、脂肪族和2-取代的吡咯烷、哌啶和氮杂环庚烷。
• FUMAGILLOL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME
  申请人：Zafgen, Inc.

  公开号：US20170066749A1

  公开（公告）日：2017-03-09

  Disclosed herein, in part, are fumagillol compounds and methods of use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making fumagillol compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.
• US9682965B2
  申请人：——

  公开号：US9682965B2

  公开（公告）日：2017-06-20