ethyl (1S,2R)-2-((tert-butoxycarbonyl)amino)cyclopent-3-enecarboxylate | 1006611-40-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (1S,2R)-2-((tert-butoxycarbonyl)amino)cyclopent-3-enecarboxylate
• 英文别名: ethyl (1S,2R)-2-tert-butoxycarbonylaminocyclopent-3-enecarboxylate；ethyl (1S,2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopent-3-ene-1-carboxylate
• CAS: 1006611-40-0
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: UIWSWVQMZXBKIH-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (1S,2R)-2-((tert-butoxycarbonyl)amino)cyclopent-3-enecarboxylate 在 potassium permanganate 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以46%的产率得到ethyl (1S,2S,3R,4S)-2-(tert-butoxycarbonylamino)-3,4-dihydroxycyclopentanecarboxylate
  参考文献：
  名称：

  A new strategy for the preparation of heterocyclic β-amino esters: orthogonally protected β-amino esters with a piperidine skeleton

  摘要：

  A simple strategy is presented for the introduction of a nitrogen atom into the carbocycle of an aminocyclopentene-carboxylic ester via dihydroxylation of the olefinic bond, followed by NaIO4-mediated cleavage of the diol intermediate and ring expansion, resulting in new regioisomeric 3-amino-4-piperidinecarboxylic acid derivatives. This method permits the preparation of amino esters with a piperidine skeleton in enantiomerically pure form. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.043
• 作为产物：
  描述：

  (1S,5R)-6-azabicyclo[3.2.0]hept-3-en-7-one 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.0h， 生成 ethyl (1S,2R)-2-((tert-butoxycarbonyl)amino)cyclopent-3-enecarboxylate
  参考文献：
  名称：

  Synthesis of densely functionalized cispentacin derivatives through selective aziridination and aziridine opening reactions: orthogonally protected di- and triaminocyclopentanecarboxylates

  摘要：

  A novel substrate-directed synthetic route to a series of highly functionalized, orthogonally protected di- or triaminocyclopentanecarboxylate derivatives with multiple chiral centres from an unsaturated bicyclic beta-lactam has been accomplished by applying stereoselective ring C-C double bond aziridination with chloramine-T and phenyltrimethylammonium tribromide, followed by regioselective aziridine opening with different N,O nucleophiles and hydrides. The functionalization strategy was successfully extended for access to enantiomerically pure orthogonally protected triaminocarboxylates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.071

文献信息

• A Selective Synthesis of Fluorinated Cispentacin Derivatives
  作者：Loránd Kiss、Melinda Nonn、Enikő Forró、Reijo Sillanpää、Santos Fustero、Ferenc Fülöp

  DOI：10.1002/ejoc.201402121

  日期：2014.7

  A facile selective method has been developed for the synthesis of new fluorine-containing cispentacin stereoisomers. Mono- and difluorinated cispentacin derivatives were synthetized from a bicyclic β-lactam in five or six steps involving a regio- and stereoselective hydroxylation through iodooxazoline formation, followed by deoxygenation by fluorination. Starting from an enantiomerically pure bicyclic

  已经开发了一种简便的选择性方法来合成新的含氟顺五霉素立体异构体。单氟化和二氟化顺喷菌素衍生物是由双环 β-内酰胺以五或六个步骤合成的，包括通过碘恶唑啉形成的区域和立体选择性羟基化，然后通过氟化脱氧。从通过外消旋化合物的酶促拆分获得的对映异构纯双环 β-内酰胺开始，对映发散程序允许制备右旋和左旋二氟化顺喷菌素。
• Synthesis of novel isoxazoline-fused cispentacin stereoisomers
  作者：Loránd Kiss、Melinda Nonn、Enikő Forró、Reijo Sillanpää、Ferenc Fülöp

  DOI：10.1016/j.tetlet.2009.03.119

  日期：2009.5

  New isoxazoline-fused cispentacins were prepared by the 1,3-dipolar cycloaddition of nitrile oxides to beta-amino esters containing a cyclopentene skeleton. This synthetic procedure gave regio- and diastereoisomers of the cispentacins. The synthetic route was extended to the synthesis of these compounds in enantiomerically pure form. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of densely functionalized cispentacin derivatives through selective aziridination and aziridine opening reactions: orthogonally protected di- and triaminocyclopentanecarboxylates
  作者：Melinda Nonn、Loránd Kiss、Enikő Forró、Reijo Sillanpää、Ferenc Fülöp

  DOI：10.1016/j.tet.2014.09.071

  日期：2014.11

  A novel substrate-directed synthetic route to a series of highly functionalized, orthogonally protected di- or triaminocyclopentanecarboxylate derivatives with multiple chiral centres from an unsaturated bicyclic beta-lactam has been accomplished by applying stereoselective ring C-C double bond aziridination with chloramine-T and phenyltrimethylammonium tribromide, followed by regioselective aziridine opening with different N,O nucleophiles and hydrides. The functionalization strategy was successfully extended for access to enantiomerically pure orthogonally protected triaminocarboxylates. (C) 2014 Elsevier Ltd. All rights reserved.
• A new strategy for the preparation of heterocyclic β-amino esters: orthogonally protected β-amino esters with a piperidine skeleton
  作者：Loránd Kiss、Brigitta Kazi、Enikő Forró、Ferenc Fülöp

  DOI：10.1016/j.tetlet.2007.11.043

  日期：2008.1

  A simple strategy is presented for the introduction of a nitrogen atom into the carbocycle of an aminocyclopentene-carboxylic ester via dihydroxylation of the olefinic bond, followed by NaIO4-mediated cleavage of the diol intermediate and ring expansion, resulting in new regioisomeric 3-amino-4-piperidinecarboxylic acid derivatives. This method permits the preparation of amino esters with a piperidine skeleton in enantiomerically pure form. (C) 2007 Elsevier Ltd. All rights reserved.