(S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-pyrrole-1-carboxylic acid tert-butyl ester | 193264-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-pyrrole-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,3-dihydropyrrole-1-carboxylate
• CAS: 193264-89-0
• 化学式: C₁₆H₃₁NO₃Si
• 分子量: 313.513
• InChiKey: MSNZFYIYTGBUNF-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四丁基氟化铵 、 sodium acetate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.5h， 生成 (2R,5S)-1-(tert-butoxycarbonyl)-2-(p-carbomethoxyamino-phenyl)-5-hydroxymethyl-3-pyrroline
  参考文献：
  名称：

  Probing the Stereoselectivity of the Heck Arylation of Endocyclic Enecarbamates with Diazonium Salts. Concise Syntheses of (2S,5R)-Phenylproline Methyl Ester and Schramm's C-Azanucleoside

  摘要：

  [GRAPHICS]The diastereoselectivity of the Heck arylation of several chiral, nonracemic, five-membered endocyclic enecarbamates with aryldiazonium tetrafluoroborates was evaluated. The cis selectivity observed for some enecarbamates bearing coordinating groups was explored in the concise synthesis of the (2S,5R)-(+)-phenylproline methyl ester, a scaffold for the nonpeptide cholecystokinin antagonist (+)-RP 66803, and in the synthesis of Schramm's potent antiprotozoan C-azanucleoside.

  DOI：

  10.1021/ol027268a
• 作为产物：
  描述：

  (2S)-N-(叔-丁基氧羰基)-O-(叔-丁基)二甲基硅烷基-焦谷氨醇 在 5-氯喹喔啉-2-磺胺 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 0.75h， 生成 (S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-pyrrole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A Convenient Procedure for the Conversion Of N-Boc Protected Pyrrolidinone Derivatives Into Their Corresponding Enecarbamates

  摘要：

  When N-Boc protected pyrrolidinone derivatives are treated by Dibal-H and then by quinolinium camphorsulfonate, they are converted into their corresponding enecarbamate.

  DOI：

  10.1080/00397919708004150

文献信息

• Stereoselective Synthesis of Aza Analogues of Isoaltholactone and Goniothalesdiol - New Applications of the Heck-Matsuda Reaction
  作者：Angélica Venturini Moro、Marcelo Rodrigues dos Santos、Carlos Roque D. Correia

  DOI：10.1002/ejoc.201100886

  日期：2011.12

  The synthesis of (–)-aza-isoaltholactone 6 was successfully accomplished in nine steps from the starting enecarbamate. We also performed the synthesis of the new fully substituted pyrrolidine (–)-(2R,3R,4S,5S)-1-(tert-butoxycarbonyl)-3,4-dihydroxy-5-phenylpyrrolidin-2-ylacrylic acid 28, which is a potential advanced intermediate in the route to aza-altholactone. Moreover, the synthesis of a new nitrogen

  描述了具有生物活性的异戊内酯和goniothalesdiol 的氮类似物的立体选择性合成。成功的策略是在合成的早期阶段以不同的方式在带有酯官能团的手性内环烯氨基甲酸酯和重氮芳烃四氟硼酸盐之间进行 Heck-Matsuda 反应。讨论了与这种关键芳基化反应相关的几个方面，以突出影响芳基化过程结果的结构特征。(-) - aza-isoaltholactone 6 的合成从起始烯氨基甲酸酯分九步成功完成。我们还合成了新的完全取代的吡咯烷 (-) - (2R, 3R, 4S, 5S) -1- (叔丁氧基羰基) -3,4-二羟基-5-苯基吡咯烷-2-基丙烯酸 28，它是氮杂-内酯路线中潜在的高级中间体。此外，从受保护的二羟基吡咯烷 (-) - 27 合成了一种新的goniothalesdiol (+) - 33 的氮类似物，该二羟基吡咯烷 (-) - 27 是通过尝试合成 aza-altholactone
• An Enantioselective Approach to <scp>Heteroatom‐Containing</scp> Bicyclic Derivatives via <scp>Inverse‐Electron‐Demand</scp> Diels−Alder Reactions
  作者：Jun‐Xiong He、Xu‐Ge Si、Qi‐Tao Lu、Qian‐Wei Zhang、Quan Cai

  DOI：10.1002/cjoc.202200441

  日期：2023.1

  important pharmacophores and prevalent in bioactive natural products and drug molecules. Herein, we report a unified approach for the divergent synthesis of chiral heteroatom-containing bicyclic derivatives by lanthanide (III)-catalyzed asymmetric inverse-electron-demand Diels–Alder reactions of 2-pyrones. These reactions occur with various readily available dihydropyrroles and dihydrofurans as dienophiles

  手性含杂原子的双环支架是重要的药效团，普遍存在于具有生物活性的天然产物和药物分子中。在此，我们报告了一种通过镧系元素 (III) 催化的 2-吡喃酮的不对称逆电子需求 Diels-Alder 反应发散合成手性含杂原子双环衍生物的统一方法。这些反应发生在各种容易获得的二氢吡咯和二氢呋喃作为亲二烯体时，为密集官能化的顺式- 氢吲哚和顺式 - 氢苯并呋喃提供了一个步骤经济的合成平台，具有优异的产率和对映选择性。(–)-α-lycorane 和 (–)-lycorine 生物碱的简明合成证明了这种方法的合成效用。
• A Convenient Procedure for the Conversion Of N-Boc Protected Pyrrolidinone Derivatives Into Their Corresponding Enecarbamates
  作者：Cossy、Cases、Gomez Pardo

  DOI：10.1080/00397919708004150

  日期：1997.8

  When N-Boc protected pyrrolidinone derivatives are treated by Dibal-H and then by quinolinium camphorsulfonate, they are converted into their corresponding enecarbamate.
• Probing the Stereoselectivity of the Heck Arylation of Endocyclic Enecarbamates with Diazonium Salts. Concise Syntheses of (2<i>S</i>,5<i>R</i>)-Phenylproline Methyl Ester and Schramm's C-Azanucleoside
  作者：Elias A. Severino、Edson R. Costenaro、Ariel L. L. Garcia、Carlos Roque D. Correia

  DOI：10.1021/ol027268a

  日期：2003.2.1

  [GRAPHICS]The diastereoselectivity of the Heck arylation of several chiral, nonracemic, five-membered endocyclic enecarbamates with aryldiazonium tetrafluoroborates was evaluated. The cis selectivity observed for some enecarbamates bearing coordinating groups was explored in the concise synthesis of the (2S,5R)-(+)-phenylproline methyl ester, a scaffold for the nonpeptide cholecystokinin antagonist (+)-RP 66803, and in the synthesis of Schramm's potent antiprotozoan C-azanucleoside.