6-(2-Hydroxy-2-phenylethyl)-6-methylfulvene | 121896-61-5

• 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: 6-(2-Hydroxy-2-phenylethyl)-6-methylfulvene
• 英文别名: 3-cyclopenta-2,4-dien-1-ylidene-1-phenylbutan-1-ol
• CAS: 121896-61-5
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: VXLLKHSEYDXKBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  6,6-二甲基-5-亚甲基-1,3-环戊二烯 、 苯甲醛 在 氢气 、 lithium diisopropyl amide 作用下， 生成 6-(2-Hydroxy-2-phenylethyl)-6-methylfulvene
  参考文献：
  名称：

  6,6-二甲基富烯的官能化：醛醇缩合的二甲苯类似物。

  摘要：

  通过使富烯基阴离子2与醛在低温下反应，将6,6-二甲基富烯基1在7位区域选择性地官能化。加合物3在低温下被捕集，并以高收率（57-82％）的形式分离为黄烯酚4或相应的三甲基甲硅烷基醚5。醛的动力学上有利的环外加成反应是通过调用边界轨道控制过程来解释的，该过程受Hückel计算的支持。

  DOI：

  10.1016/s0040-4039(00)80663-2

文献信息

• Scope and Limitations of Fulvene Syntheses. Preparation of 6-Vinyl-Substituted and -Functionalized Fulvenes. First Examples of Nucleophilic Substitution on a 6-(Chloromethyl)fulvene
  作者：Ihsan Erden、Fu-Pei Xu、Aladin Sadoun、Wyatt Smith、Greg Sheff、Madeleine Ossun

  DOI：10.1021/jo00109a010

  日期：1995.2

  Very few 6-vinylfulvenes have previously been reported in the Literature. In a few cases where Little's procedure (using pyrrolidine as base) has been employed, most enones undergo conjugate attack by the cyclopentadienyl anion followed by either a retroaldol reaction or dihydropentalene formation. In several cases, Diels-Alder reaction of the enone with cyclopentadiene occurs rather than condensation. We have found that in cases where the Little procedure fails to give the desired 6-vinylfulvenes, the Thiele method using NaOH (or NaOMe in some cases) as base gives satisfactory results. In the latter instances, Michael attack is completely suppressed in all but one example. By appropriate choice of base, a variety of fulvenes carrying functional groups on the 6-alkyl position can be prepared. Some of these fulvenes have been shown to undergo further functional group transformations (e.g., nucleophilic substitutions); giving rise to derivatives bearing SR, S(O)R, N-3 or SCN groups.
• NYSTROM, JAN-ERIK;BYSTROM, STYRBJORN;RISTOLA, TAINA;EKSTROM, JOHN, TETRAHEDRON LETT., 29,(1988) N 39, C. 4997-5000
  作者：NYSTROM, JAN-ERIK、BYSTROM, STYRBJORN、RISTOLA, TAINA、EKSTROM, JOHN

  DOI：——

  日期：——