(E)-1,1-dimethoxycarbonyle-2-benzylidene cyclopentane | 131190-07-3

• 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: (E)-1,1-dimethoxycarbonyle-2-benzylidene cyclopentane
• 英文别名: 2-benzylidenecyclopentane-1,1-dicarboxylic acid dimethyl ester；dimethyl (2E)-2-benzylidenecyclopentane-1,1-dicarboxylate；2-((E)-benzylidene)-1,1-bis(methoxycarbonyl)cyclopentane；dimethyl (2E)-2-benzylidene-1,1-cyclopentanedicarboxylate
• CAS: 131190-07-3
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: DGHGOTXGIVUHSH-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1,1-dimethoxycarbonyle-2-benzylidene cyclopentane 在 碘代三甲硅烷 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Synthesis of stereodefined fused δ-hydroxy-γ-lactones from dealkylative cyclization of epoxy-diesters

  摘要：

  A dealkylative lactonization of stereodefined aryl-substituted epoxides allows the preparation of densely functionalized fused delta-hydroxy-gamma-lactones having three consecutive stereochemically defined stereocenters. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.106
• 作为产物：
  描述：

  α-phenylsulfonylmethylacetoacetate 在 potassium tert-butylate 、 乙基二苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 生成 (E)-1,1-dimethoxycarbonyle-2-benzylidene cyclopentane
  参考文献：
  名称：

  Stereospecific synthesis of arylidene and allylidene cyclopentanes by a palladium-catalyzed cylisation

  摘要：

  DOI：

  10.1016/s0040-4039(00)97827-4

文献信息

• Pd-catalyzed intramolecular addition of active methylene compounds to alkynes with subsequent cross-coupling with (hetero)aryl halides
  作者：Aleksandra Błocka、Paweł Woźnicki、Marek Stankevič、Wojciech Chaładaj

  DOI：10.1039/c9ra08002c

  日期：——

  Pd-catalyzed intramolecular addition of active methylene compounds to alkynes, followed by subsequent cross-coupling with (hetero)aryl bromides and chlorides. The reaction proceeds under mild conditions, providing excellent functional group tolerance, including unprotected OH, NH2 groups, enolizable ketones, or a variety of heterocycles. Mechanistic studies point towards a catalytic cycle involving oxidative

  我们报告了一种有效的方案，用于串联 Pd 催化的活性亚甲基化合物与炔烃的分子内加成，然后与（杂）芳基溴化物和氯化物进行交叉偶联。该反应在温和条件下进行，提供优异的官能团耐受性，包括未保护的 OH、NH 2基团、可烯醇化的酮或各种杂环。机理研究表明催化循环涉及氧化加成、对 Pd( II ) 活化的炔烃的分子内亲核加成和还原消除，其中 5 -exo-dig环化是限速步骤。
• THF: An Efficient Electron Donor in Continuous Flow Radical Cyclization Photocatalyzed by Graphitic Carbon Nitride
  作者：Magdalena Woźnica、Nicolas Chaoui、Soraya Taabache、Siegfried Blechert

  DOI：10.1002/chem.201404440

  日期：2014.11.3

  Mesoporous graphitic carbon nitride (mpg‐C3N4) was found to be an efficient heterogeneous photocatalyst for the metal‐free radical cyclization of 2‐bromo‐1,3‐dicarbonyl compounds. Reactions leading to functionalized cyclopentanes proceed under mild conditions and can be conducted in a continuous flow photoreactor. Compared to the batch reaction, the use of a continuous flow reactor resulted in a significant

  发现介孔石墨碳氮化物（mpg-C 3 N 4）是2-溴-1,3-二羰基化合物的金属自由基环化的有效多相光催化剂。导致官能化的环戊烷的反应在温和的条件下进行，可以在连续流动的光反应器中进行。与分批反应相比，使用连续流动反应器可显着减少反应时间（4小时后，批次中0.04 mmol底物的完全转化，而在流动反应器中，相同量的底物可以完全转化）在40分钟内转化为产品）。该反应的机理研究表明，THF不仅起溶剂的作用，而且还是至关重要的氢和电子给体。
• Synthese de (e)-arylidene et allylidene cyclopentanes par une annelation catalysee par un complexe de palladium(0)
  作者：Guy Fournet、Geneviève Balme、Jacques Gore

  DOI：10.1016/s0040-4020(01)86561-3

  日期：1991.8

  When treated with an unsaturated halide in a palladium-catalyzed process, the anions from gamma-acetylenic malonates 4 and 5 stereospecifically lead to cyclopentanes having an exo tri- or tetra-substituted double bond. This reaction which forms simultaneously two carbon-carbon bonds is believed to proceed by nucleophilic attack of the anion on the triple bond activated by the sigma-aryl or sigma-vinyl palladium complex.
• An X⁻ (X = I, Br)-Triggered Ring-Opening Cyclization of Cyclopropenyl-Substituted Alkyl Halides or Mesylates: An Efficient and Highly Regio- and Stereoselective Approach to (<i>E)</i>-Haloalkylidene 4−7-Membered Cyclic Compounds
  作者：Jie Chen、Shengming Ma

  DOI：10.1021/jo900389m

  日期：2009.8.7

  Polyfunctionalized (E)-haloalkylidene cyclic products were efficiently synthesized in moderate to excellent yields via a regio- and stereoselective X- (X = I or Br)-triggered ring-opening intramolecular trapping of cyclopropenes 1. The reaction can be used for construction of 4-7-membered products. The E-stereoselectivity of the exo-C=C bond is very high. The carbon-halogen bond in the exo-C=C bond may further be elaborated to prepare differently substituted cyclic products with a stereodefined C=C bond.