(2-Methoxyethyl)cyclopentadien | 90198-72-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-Methoxyethyl)cyclopentadien
• 英文别名: (2-methoxyethyl)cyclopentadiene；2-cyclopentadien-1-yl-ethyl methyl ether；5-(2-Methoxyethyl)cyclopenta-1,3-diene
• CAS: 90198-72-4
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: DCGHMSUJIRBLRO-UHFFFAOYSA-N

物化性质

• 沸点：
  40 °C(Press: 4 Torr)
• 密度：
  0.914±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-Methoxyethyl)cyclopentadien 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到Kalium-(2-methoxyethyl)cyclopentadienid
  参考文献：
  名称：

  Herrmann, Wolfgang A.; Anwander, Reiner; Munck, Florian C., Chemische Berichte, 1993, vol. 126, # 2, p. 331 - 338

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯乙基甲基醚 、 sodium cyclopentadienide 以 四氢呋喃 为溶剂， 生成 (2-Methoxyethyl)cyclopentadien
  参考文献：
  名称：

  Synthesis, characterization and cytotoxicity studies of methoxy alkyl substituted metallocenes

  摘要：

  Five titanocene derivatives and one zirconium analogous, having cyclopentadienylethenylmethoxy ligand, were synthesized and fully characterized by NMR, FT-IR, and elemental analysis. Two of these complexes showed a good cytotoxic activity on human breast cancer (MCF-7) cell lines. Moreover, the half-titanocene disclosed also a good cytotoxic activity on human embryonic kidney (HEK-293). Additionally, a study on the rate of hydrolysis of these compounds showed that the leaving groups significantly affect the rate of hydrolysis of cyclopentadienyl groups too. The different activity of synthesized compounds was tentatively related to the rate of hydrolysis. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.10.021

文献信息

• Synthesis of New Chiral Cyclopentadienes Suited for Chelation
  作者：Qichen Huang、Yanlong Qian

  DOI：10.1055/s-1987-28118

  日期：——

  A new family chiral cyclopentadienes suitable for chelation are obtained by the functionalization of sodium cyclopentadienide with chiral tosylates.

  通过将环戊二烯钠与手性对甲苯磺酸盐官能化，获得了适用于螯合的新型手性环戊二烯家族。
• Synthesis of cyclopentadienyl ruthenium(II) complexes containing tethered functionalities
  作者：Wei Lin Janet Leong、Marc V. Garland、Lai Yoong Goh、Weng Kee Leong

  DOI：10.1016/j.ica.2008.09.026

  日期：2009.4

  The reaction of [C5H4(CH2)(n)X]Tl (1: n = 2, X = NMe2, OMe, CN; n = 3, X = NMe2) with [(eta(6)-C6H6) RuCl(mu-Cl)](2), 2, afforded the sandwich compounds [eta(5)-C5H4(CH2)(n)X}Ru(eta(6)-C6H6)]PF6, 3, and [eta(5)-C5H4-(CH2)(n)X](2)Ru, 4. Photolytic cleavage of 3 in acetonitrile afforded the tethered products [eta(5): kappa N-C5H4(CH2)(n)X}Ru(CH3CN)(2)]PF6, 5. (C) 2008 Elsevier B.V. All rights reserved.
• Titanocenes and zirconocenes with (chiral) O-functionalized side chains on the Cp ring
  作者：Adolphus A.H van der Zeijden、Chris Mattheis

  DOI：10.1016/s0022-328x(97)00698-0

  日期：1998.3

  A series of titanocene and zirconocene dichlorides was synthesized bearing ligands that contain a (chiral) ether group linked by an ethylene spacer group to the cyclopentadienyl ring. Surprisingly, the chiral zirconocenes (eta(5)-C5H4CH2CH2OR)(2)ZrCl2 with R = isobornyl and menthyl do not show Ziegler-Natta activity. This is probably caused by attack of the cocatalyst (MeAlO)(n) on the side chains, causing immobilization of the catalyst. Intramolecular coordination of the side chains is provoked by converting the dichlorides to the more Lewis-acidic mono and bis triflate complexes. The coordination of the ether chain depends on the size of the terminal group in the chain. In the achiral derivative (eta(5)-C5H4CH2CH2OMe)(2)Zr(O3SCF3)(2) there is a rapid equilibrium between species with one and two intramolecularly-coordinated ether side chains. The monotriflate complex (eta(5)-C(5)H(4)CH(2)CH(2)Oiso bornyl)(2)ZrCl(O3SCF3) decomposes rapidly, because ether coordination results in facile C-O bond cleavage and liberation of camphene. Accordingly, the bistriflate (eta(5)-C(5)H(4)CH(2)CH(2)Oisobornyl)(2)Zr(O3SCF3)(2) could not be synthesized. The chiral triflate complexes (eta(5)-C5H4CH2CH2OR)(2)Zr(O3SCF3)(2) with R = menthyl and fenchyl are active Diels-Alder catalysts, although no optical induction was observed, probably because the chiral ether handles are not sufficiently coordinated during catalysis. (C) 1998 Elsevier Science S.A. All rights reserved.
• HUANG, QICHEN;QIAN, YANLONG, SYNTHESIS,(1987) N 10, 910-912
  作者：HUANG, QICHEN、QIAN, YANLONG

  DOI：——

  日期：——
• US2023/212196
  申请人：——

  公开号：——

  公开（公告）日：——