1-ferrocenylisochromane | 620168-62-9

• 英文名称: 1-ferrocenylisochromane
• CAS: 620168-62-9
• 化学式: C₁₉H₁₈FeO
• 分子量: 318.198
• InChiKey: ZDDODDKPXNINEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  methyl 2-(ferrocenoyl)benzeneacetate 在 NaBH₄ 作用下， 以 乙醇 、 水 为溶剂， 以78%的产率得到2-(α-hydroxyferrocenyl)benzeneethanol
  参考文献：
  名称：

  Ferrocene compounds. XXXIX.

  摘要：

  In the title compound, [Fe(C5H5)(C14H13O)], the plane of the heterocyclic ring is almost perpendicular to the plane of the substituted cyclopentadienyl ring, and the heterocyclic ring adopts a half-chair conformation. The conformation of the nearly parallel cyclopentadienyl (Cp) rings [the dihedral angle between their planes is 2.7 (1)degrees] is almost halfway between eclipsed and staggered, and the rings are mutually twisted by about 19.4 (2)degrees (mean value). The mean lengths of the C - C bonds in the substituted and unsubstituted cyclopentadienyl ring are 1.420 (2) and 1.406 (3) Angstrom, respectively, and the Fe - C distances range from 2.029 (2) to 2.051 (2) Angstrom. The phenyl and unsubstituted cyclopentadienyl rings are involved in C - H ...pi interactions, with intermolecular H ...centroid distances of 2.85 and 3.14 Angstrom for C - H ...pi(Ph), and 2.88 Angstrom for C - H ...pi(Cp). In two of these interactions, the C - H bond points towards one of the ring bonds rather than towards the ring centroid. In the crystal structure, the C - H ...pi interactions connect the molecules into a three-dimensional framework.

  DOI：

  10.1107/s0108270103011703

文献信息

• Experimental and DFT study of cyclodehydration and acetylation of ferrocenyl diols
  作者：Jasmina Lapić、Aleksandar Višnjevac、Mario Cetina、Senka Djaković、Valerije Vrček、Vladimir Rapić

  DOI：10.1016/j.molstruc.2012.03.071

  日期：2012.7

  ferrocenyl-2-(2-hydroxymethylphenyl)ethanol ( 7 ), and ferrocenyl(2-(2-hydroxyethyl)phenyl)methanol ( 9 ) have been prepared by reduction of corresponding ketoesters using NaBH 4 in a mixture EtOH and Et 2 O. In the course of these reactions new cyclic ethers 1-ferrocenyl-2-oxaindane ( 3 ), 3-ferrocenylisochromane ( 8 ), and 1-ferrocenylisochromane ( 10 ) have been isolated as side-products. Intramolecular cyclizations

  摘要 外消旋二茂铁二醇，即二茂铁（2-羟甲基苯基）甲醇（ 2 ）、二茂铁基-2-（2-羟甲基苯基）乙醇（ 7 ）和二茂铁基（2-（2-羟乙基）苯基）甲醇（ 9 ）已被制备。通过在 EtOH 和 Et 2 O 的混合物中使用 NaBH 4 还原相应的酮酯。在这些反应过程中，新的环醚 1-二茂铁基-2-氧茚烷 (3)、3-二茂铁基异色烷 (8) 和 1-二茂铁基异色烷 (10) ) 作为副产品被分离出来。二茂铁二醇的分子内环化发生在酸性和中性介质中。密度泛函理论 (BP86) 计算用于解释这些环脱水的机制。酸催化反应遵循经典的 SN 1 机制，而在中性介质中的环化脱水被描述为 SN 2 反应。已对新的环醚产品进行 X 射线衍射分析。二茂铁二醇2、7和9分别与乙酸酐反应得到单乙酸酯11、13和15。乙酸乙烯酯对外消旋二醇的立体选择性酰化已被各种脂肪酶催化，并且在卡门氏青霉脂肪酶存在下观察到二醇 2