| 552839-04-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• CAS: 552839-04-0
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: RIHLZUIWKXVKAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 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70%的产率得到methyl 3-((Z)-cyclohept-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-cycloheptenyl acetate 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。
• PdII-Catalyzed Aerobic Allylic Oxidative Carbocyclization of Allene-Substituted Olefins: Immobilization of an Oxygen-Activating Catalyst
  作者：Julio Piera、Katja Närhi、Jan-E. Bäckvall

  DOI：10.1002/anie.200602421

  日期：2006.10.20
• 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。
• Gold-Catalyzed Cyclization of Allene-Substituted Malonate Esters:  Synthesis of <i>β</i>,<i>γ</i>-Unsaturated <i>δ</i>-Lactones
  作者：Julio Piera、Patrik Krumlinde、Dirk Strübing、Jan-E. Bäckvall

  DOI：10.1021/ol070793v

  日期：2007.5.1

  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.