| 552839-03-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 552839-03-9
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: IIEUVKPCKWTWAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  在 gold(III) chloride 、 silver hexafluoroantimonate 、 溶剂黄146 作用下， 以61%的产率得到methyl 3-(cyclopent-2-enyl)-3,6-dihydro-6,6-dimethyl-2-oxo-2H-pyran-3-carboxylate
  参考文献：
  名称：

  Gold-Catalyzed Cyclization of Allene-Substituted Malonate Esters:  Synthesis of β,γ-Unsaturated δ-Lactones

  摘要：

  An efficient method for the preparation of beta,gamma-unsaturated delta-lactones has been developed. The starting materials for the synthesis of these compounds are allene-substituted malonates which undergo gold-catalyzed cyclization by means of nucleophilic attack of the ester moiety on the allene. It is worth mentioning that this is the first example where an ester group attacks as a nucleophile in a gold-catalyzed transformation of allenes.

  DOI：

  10.1021/ol070793v
• 作为产物：
  描述：

  2-(1-环戊烯基)乙酸酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  钯 (II) 催化烯丙基氧化中的碳-碳键形成：丙二烯取代烯烃的新型氧化碳环化

  摘要：

  开发了一种新的高效钯（II）催化氧化碳环化。发现丙二烯取代的烯烃1在1mol％Pd(O 2 CCF 3 ) 2 和对苯醌(2当量)存在下环化，以良好至极好的产率得到双环系统2。环化构成了丙二烯和烯烃在氧化条件下形成的新型碳-碳键形成反应。

  DOI：

  10.1021/ja029505a

文献信息

• An Unexpectedly Mild Thermal Alder−Ene-Type Cyclization of Enallenes
  作者：Katja Närhi、Johan Franzén、Jan-E. Bäckvall

  DOI：10.1021/jo060013g

  日期：2006.3.31

  A mild, thermal Alder−ene reaction of enallenes has been developed. The allenic double bond acts as the “ene” and generates a carbon−carbon bond to an unactivated olefinic “enophile” in DMF at 120 °C to give [n.3.0] bicyclic systems (n = 3−5) in good yields. Except for a minor [2 + 2] cycloaddition byproduct, the reaction proceeded with complete atom economy, as there is no requirement of a catalyst

  已经开发了温和的烯属烃热的Alder-ene反应。烯丙基双键充当“烯”，并在120°C下与未活化的烯烃“亲烯体”产生碳-碳键，从而以高收率得到[ n .3.0]双环体系（n = 3-5）。除了少量的[2 + 2]环加成副产物外，该反应以完全的原子经济性进行，因为不需要催化剂或其他反应物，并且在此过程中不会形成废产物。
• Palladium-Catalyzed Oxidative Borylative Carbocyclization of Enallenes
  作者：Andreas K. Å. Persson、Tuo Jiang、Magnus T. Johnson、Jan-E. Bäckvall

  DOI：10.1002/anie.201008032

  日期：2011.6.27

  An efficient oxidative carbocyclization/borylation of enallenes uses Pd(OAc)2 as the catalyst, B2pin2 as the boron‐transfer reagent, and 1,4‐benzoquinone (BQ) as the oxidant (see scheme). The reaction seems to take place through activation of the allene by a PdII complex to give an alkenyl–PdII intermediate followed by carbopalladation of the olefin and subsequent cleavage of the intermediate palladium–carbon

  一种有效的氧化enallenes的carbocyclization /硼基化使用的Pd（OAC）2作为催化剂，B 2销2作为硼转移试剂，和1,4-苯醌（BQ）作为氧化剂（参见方案）。该反应似乎是通过Pd II络合物活化丙二烯生成链烯基-Pd II中间体，然后烯烃进行碳钯催化，随后硼试剂裂解中间的钯-碳键而发生的。
• Carbon−Carbon Bond Formation in Palladium(II)-Catalyzed Allylic Oxidation:  A Novel Oxidative Carbocyclization of Allene-Substituted Olefins
  作者：Johan Franzén、Jan-E. Bäckvall

  DOI：10.1021/ja029505a

  日期：2003.5.1

  efficient palladium(II)-catalyzed oxidative carbocyclization has been developed. It was found that allene-substituted olefins 1 cyclized in the presence of 1 mol % Pd(O2CCF3)2 and p-benzoquinone (2 equiv) to give bicyclic ring systems 2 in good to excellent yields. The cyclization constitutes a new type of carbon-carbon bond forming reaction between an allene and an olefin under oxidative conditions

  开发了一种新的高效钯（II）催化氧化碳环化。发现丙二烯取代的烯烃1在1mol％Pd(O 2 CCF 3 ) 2 和对苯醌(2当量)存在下环化，以良好至极好的产率得到双环系统2。环化构成了丙二烯和烯烃在氧化条件下形成的新型碳-碳键形成反应。
• Palladium-Catalyzed Oxidative Carbocyclization/Arylation of Enallenes
  作者：Tuo Jiang、Andreas K. Å. Persson、Jan-E. Bäckvall

  DOI：10.1021/ol202451f

  日期：2011.11.4

  A stereoselective palladium-catalyzed oxidative carbocyclization/arylation of enallenes is described. The reaction shows wide tolerance toward highly functionalized arylboronic acids and results in a cis addition of two carbon moieties to an olefin in good to excellent yields.

  描述了烯键烯的立体选择性钯催化的氧化碳环化/芳基化。该反应显示出对高度官能化的芳基硼酸的宽耐受性，并导致两个碳部分顺式加成至烯烃，收率良好至优异。
• Palladium(0)-Catalyzed Cycloisomerization of Enallenes
  作者：Katja Närhi、Johan Franzén、Jan-E. Bäckvall

  DOI：10.1002/chem.200500303

  日期：2005.11.18

  A novel palladium(0)-catalyzed cycloisomerization of enallenes has been developed. This reaction, catalyzed by [Pd(dba)2] (dba=dibenzylideneacetone) in acetic acid, results in the formation of cyclopentene derivatives and [n.3.0]bicyclic systems (n=3, 4) in good to high yields. The carbon-carbon bond-forming step is highly stereoselective to give cis-fused bicyclic systems. The presence of acetic acid

  已开发了新型的钯（0）催化烯烯的环异构化。该反应由[Pd（dba）2]（dba =二亚苄基丙酮）在乙酸中催化，导致形成环戊烯衍生物和[n.3.0]双环体系（n = 3、4），产率高至高。碳-碳键形成步骤是高度立体选择性的，以产生顺式稠合双环系统。为了提供良好的反应性和区域选择性，反应中必不可少的是乙酸作为溶剂和dba作为钯（0）的配体存在。