cyclopenta-2,4-dien-1-ylidenecycloheptane | 4401-17-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: cyclopenta-2,4-dien-1-ylidenecycloheptane
• 英文别名: 6,6-hexamethylenefulvene
• CAS: 4401-17-6
• 化学式: C₁₂H₁₆
• 分子量: 160.259
• InChiKey: UXJMPNOASYSGLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  cyclopenta-2,4-dien-1-ylidenecycloheptane 在 5,10,15,20-tetrakisphenylporphyrin 、 氧气 、 potassium diazodicarboxylate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (1S,4R)-7-Cycloheptylidene-2,3-dioxa-bicyclo[2.2.1]heptane
  参考文献：
  名称：

  Unusual endoperoxide isomerizations: a convenient entry into 2-vinyl-2-cyclopentenones from saturated fulvene endoperoxides

  摘要：

  An unusual peroxide base-promoted isomerization is uncovered. Saturated endoperoxides derived from fulvenes give rise to 2-vinyl-2-cyclopentenones upon treatment with DBU in CH2CL2 in a one-pot reaction. This methodology is applied to a convenient synthesis of dihydrojasmone. Moreover, functional groups placed on the side chain at C-6 participate in the base-catalyzed isomerizations via conjugate attack at the enone moiety to give 2-cyclopentenones carrying oxygen heterocycles at C-2. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.107
• 作为产物：
  描述：

  环戊二烯 、 环庚酮 在 四氢吡咯 作用下， 以 甲醇 为溶剂， 以60%的产率得到cyclopenta-2,4-dien-1-ylidenecycloheptane
  参考文献：
  名称：

  通过有机光氧化还原催化的可见光诱导的 [4 + 2] 五富烯环加成。

  摘要：

  我们开发了在室温下绿光照射下硫代黄鎓光氧化还原催化的五富烯的 [4 + 2] 环加成反应，得到具有高区域选择性的四氢环戊二烯[ b ]色烯。本反应提供了一种可持续的方法来进行五富烯的环加成，而无需使用过渡金属催化剂或高温条件。该程序可以温和而直接地获得 1,3a,9,9a-四氢环戊二烯[ b ]色烯。反应的量子产率（Φ =0.15）表明反应主要通过光催化途径进行。

  DOI：

  10.1039/d0ob01151g

文献信息

• Reaction of dicyclopentadienylyttrium chloride with aldehydes and ketones. A novel cleavage reaction of CpY π-bond
  作者：Changtao Qian、Aineng Qiu

  DOI：10.1016/s0040-4039(00)88478-6

  日期：1988.1

  Dicyclopentadienylytrrium chloride reacts with aldehydes and ketones at 80°C in DME, generating fulvenes in excellent yields, while at lower temperature affording, after hydrolysis, cyclopentadienyl substituted alcohols.

  二环戊二烯基氯化t在DME中于80°C与醛和酮反应，以优异的收率产生富烯，同时在较低的温度下水解后提供环戊二烯基取代的醇。
• Expeditious synthesis of N-bridged heterocycles via dipolar cycloaddition of pentafulvenes with 3-oxidopyridinium betaines
  作者：Jinesh M. Kuthanapillil、Sreeja Thulasi、Rani Rajan、K. Syam Krishnan、E. Suresh、K.V. Radhakrishnan

  DOI：10.1016/j.tet.2010.11.084

  日期：2011.2

  A new and highly versatile approach towards the synthesis of bicyclo[6.3.0]undecanes and bicyclo[5.3.0]decanes was accomplished. The methodology adopted involved [6+3] and [3+2] cycloaddition reactions of pentafulvenes with 3-oxidopyridinium betaines generated either by the action of a base on the pyridinium salt or thermally from pyridinium betaine dimer. These well-functionalized bicyclo[6.3.0]undecanes

  完成了一种新的，用途广泛的合成双环[6.3.0]十一烷和双环[5.3.0]癸烷的方法。所采用的方法学涉及五氟丁苯与3-氧化吡啶鎓甜菜碱的[6 + 3]和[3 + 2]环加成反应，该甜菜碱通过在吡啶鎓盐上的碱作用或吡啶鎓甜菜碱二聚体的热作用生成。这些功能良好的双环[6.3.0]十一烷和双环[5.3.0]癸烷提供了广泛的合成选择，可以预期将其转化为多种快速有效的天然产物合成方法。
• Lewis acid catalyzed Povarov reaction of pentafulvenes and spiro[2,4]-hepta-[4,6]-diene: An efficient access to cyclopentene fused quinolines
  作者：Shreyass Saranya、Thekke Veettil Baiju、Greeshma Gopalan、Kokkuvayil Vasu Radhakrishnan

  DOI：10.1080/00397911.2018.1427270

  日期：2018.4.3

  ABSTRACT An efficient protocol for the Lewis acid catalyzed three-component aza-Diels-Alder reaction of pentafulvenes as dienophile has been developed. Cyclopentene fused tetrahydroquinolines were formed in good yields with excellent diastereoselectivities. The method was extended to spiro[2,4]hepta-4,6-diene, by which 3,4-dihydroquinoline derivatives were obtained. The aromatization of cycloadducts

  摘要 已经开发了一种用于路易斯酸催化的五富烯作为亲二烯体的三组分氮杂-狄尔斯-阿尔德反应的有效方案。环戊烯稠合的四氢喹啉以良好的收率和优异的非对映选择性形成。该方法扩展到螺[2,4]庚-4,6-二烯，由此获得3,4-二氢喹啉衍生物。环加合物的芳构化提供相应的喹啉衍生物。图形概要
• C1-Bridged fluorenylidene cyclopentadienylidene complexes of the type (C13H8–CR1R2–C5H3R)ZrCl2 (R1, R2=alkyl, phenyl, alkenyl; R=H, alkyl, alkenyl, substituted silyl) as catalyst precursors for the polymerization of ethylene and propylene
  作者：Helmut G. Alt、Michael Jung

  DOI：10.1016/s0022-328x(98)00740-2

  日期：1998.10

  The synthesis and characterization of 14 new C1-bridged fluorenylidene cyclopentadienylidene complexes of zirconium is described. After activation with methylaluminoxane (MAO), these metallocene complexes can be used for the polymerization of ethylene and propylene. Various substituents in the bridge and in position 3 of the cyclopentadienylidene ligand have a strong influence on the activity of the

  描述了14种新的锆的C 1-桥联芴基环戊二烯基亚配合物的合成和表征。用甲基铝氧烷（MAO）活化后，这些茂金属络合物可用于乙烯和丙烯的聚合。环戊二烯亚基配体的桥中和3位上的各种取代基对相应催化剂的活性和所形成的聚烯烃的分子量具有强烈的影响。环戊二烯基亚环的3位上的取代基的体积决定了丙烯的立体定向聚合的程度。可以选择产生半规，间规或等规聚丙烯和/或相应的嵌段共聚物的取代基。
• Broad Scope [4 + 2] Cycloaddition of <i>o</i>-Carboryne with Pentafulvenes Using 1-Li-2-OTf-<i>o</i>-C₂B₁₀H₁₀ as Precursor
  作者：Jie Zhang、Zaozao Qiu、Zuowei Xie

  DOI：10.1021/acs.organomet.7b00574

  日期：2017.10.9

  from 1-Li-2-OTf-o-C2B10H10 undergoes an efficient [4 + 2] cycloaddition with pentafulvenes at room temperature to give a series of carboranonorbornenes in good to high isolated yields. This reaction is compatible with many functional groups and has a very broad substrate scope from 6-mono- to 6,6′-disubstituted pentafulvenes and from alkyl to aryl substituents. Further transformations of the resultant

  从1-Li-2-OTf- o -C 2 B 10 H 10原位生成的邻-碳硼烷（1,2-脱氢-邻-甲硼烷）在室温下进行有效的[4 + 2]环戊五烯加成反应，得到一系列高或高分离产率的碳硼烷降冰片烯。该反应与许多官能团相容，并且具有非常宽的底物范围，从6-单-至6,6'-二取代的五氟戊烯和从烷基至芳基取代基。已经对所得的[4 + 2]环加成产物进行了进一步的转化，从而提供了各种多功能的邻氨基甲酸酯。