(1S,4R)-cis-4-phthalimido-2-cyclopent-1-yl pivalate | 281660-73-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (1S,4R)-cis-4-phthalimido-2-cyclopent-1-yl pivalate
• 英文别名: [(1S,4R)-4-(1,3-dioxoisoindol-2-yl)cyclopent-2-en-1-yl] 2,2-dimethylpropanoate
• CAS: 281660-73-9
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: HQFROKRNBPDARV-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,4R)-cis-4-phthalimido-2-cyclopent-1-yl pivalate 在 过氧乙酸 、 四氧化锇 、 potassium metaperiodate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 48.0h， 生成 (2R,4S)-2-(2,2-Dimethyl-propionyloxy)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentanedioic acid
  参考文献：
  名称：

  Thalidomide metabolites. Part 1: Derivatives of (+)-2-(N-phthalimido)-γ-hydroxyglutamic acid

  摘要：

  A mild version of the Lemieux-Johnson olefin cleavage followed by a peroxide-mediated dialdehyde oxidation and esterification effected the conversion of 1-acyloxy-4-N-phthalimido-2-cyclopentenyl esters to gamma-oxygenated-N-phthalimidoglutamic ester derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00160-x
• 作为产物：
  描述：

  (1S,4R)-顺式-4-乙酰氧基-2-环戊烯-1-醇 在 四(三苯基膦)钯 4-二甲氨基吡啶 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (1S,4R)-cis-4-phthalimido-2-cyclopent-1-yl pivalate
  参考文献：
  名称：

  Thalidomide metabolites. Part 1: Derivatives of (+)-2-(N-phthalimido)-γ-hydroxyglutamic acid

  摘要：

  A mild version of the Lemieux-Johnson olefin cleavage followed by a peroxide-mediated dialdehyde oxidation and esterification effected the conversion of 1-acyloxy-4-N-phthalimido-2-cyclopentenyl esters to gamma-oxygenated-N-phthalimidoglutamic ester derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00160-x

文献信息

• Palladium(0)-Mediated Preparation of<i>trans</i>-4-Substituted-1-(phthalimido)-2-cyclopentenes
  作者：Frederick A. Luzzio、Alexander V. Mayorov

  DOI：10.1055/s-2003-37516

  日期：——

  The series of title compounds were found to be conven­iently available from the corresponding trans-4-chloro-1-(phthalimido)-2-cyclopentene. The allylic chlorocycloalkene was found to be an excellent substrate for Pd(0)-mediated acyloxylation with the salts of carboxylic acids. Using the allylic chlorocycloalkene as a coupling partner, the Pd(0)-mediated alkylation with active methylene compounds was facilitated in variable yields by promotion with organic bases such as DBU and 1,1,3,3-tetramethylguanidine. Using the Pd(0)-mediated protocol, the product 4-substituted-trans-1-phthalimido-2-cyclopentenes were obtained in modest to excellent yields overall.

  一系列标题化合物被发现可方便地从相应的trans-4-氯-1-(呋喃酰胺)-2-环戊烯中获得。该烯丙基氯环烯烃被发现是Pd(0)介导的羧酸盐酰氧化反应的优良底物。使用烯丙基氯环烯烃作为耦合伙伴，通过有机碱（如DBU和1,1,3,3-四甲基氨基脲）的促进，Pd(0)介导的活性亚甲基化反应获得了可变的产率。在Pd(0)介导的反应过程中，最终获得4取代的trans-1-呋喃酰胺-2-环戊烯，整体产率从中等到优秀。