2-(1-bromo-ethyl)-tetrahydro-furan | 94922-02-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-(1-bromo-ethyl)-tetrahydro-furan
• 英文别名: 2-(1-Brom-aethyl)-tetrahydro-furan；2-(1-Bromoethyl)oxolane
• CAS: 94922-02-8
• 化学式: C₆H₁₁BrO
• 分子量: 179.057
• InChiKey: RWIWPJLUZGXDOL-UHFFFAOYSA-N

物化性质

• 沸点：
  192.7±13.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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-(1-bromo-ethyl)-tetrahydro-furan 在 乙醚 、 sodium 作用下， 生成 4-己烯-1-醇
  参考文献：
  名称：

  Ficini, Bulletin de la Societe Chimique de France, 1956, p. 119,122

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(四氢呋喃-2-基)乙醇 在 吡啶 、 三溴化磷 作用下， 生成 2-(1-bromo-ethyl)-tetrahydro-furan
  参考文献：
  名称：

  346.烯烃化合物的立体化学研究。第二部分 2–1'-卤代烷基四氢呋喃和3-卤代-2-烷基-四氢吡喃的断环反应是制备已知构型的烷-4-烯-1-醇的方法，也是通过五个亚甲基进行扩链的方法

  摘要：

  DOI：

  10.1039/jr9500001707

文献信息

• A new easy method for the synthesis of cyclic halogenoethers and halogenolactones
  作者：Morris Srebnik、Raphael Mechoulam

  DOI：10.1039/c39840001070

  日期：——

  Oxidation of halogen salts with m-chloroperbenzoic acid in the presence of 18-crown-6 and of suitable hydroxy or carboxy alkenes leads readily to high yield production of cyclic halogenoethers of halogenolactones.

  卤素盐的氧化，米在合适的羟基或羧基的烯烃引线容易以高产率生产halogenolactones的环状halogenoethers的18-冠-6的存在下和氯过苯甲酸。
• Br⁺ and I⁺ Transfer from the Halonium Ions of Adamantylideneadamantane to Acceptor Olefins. Halocyclization of 1,ω-Alkenols and Alkenoic Acids Proceeds via Reversibly Formed Intermediates
  作者：A. A. Neverov、R. S. Brown

  DOI：10.1021/jo951703f

  日期：1996.1.1

  The kinetics of the transfer of X(+) from the bromonium and iodonium ions of adamantylideneadamantane (1-Br+ and 1-I-) to some 1,omega-alkenols and alkenoic acids in ClCH2CH2Cl at 25 degrees C was investigated. In all cases, the expected products of halocyclization were observed. For the iodonium ion transfer the reaction kinetics are second order overall, first order in both 1-I+ and acceptor olefin. Transfer of the bromonium ion from 1-Br+ to these acceptor olefins exhibits different kinetic characteristics. In most cases, the rate of the Br+ transfer is subject to strong retardation in the presence of added parent olefin (Ad=Ad), suggestive of a common species rate depression. In some cases, such as 4-penten-1-ol (2b) and 4-pentenoic acid (4b), the reaction can be completely suppressed at high [Ad=Ad]. In other cases, such as 3-buten-1-ol (2a), 5-hexen-1-ol (2c), cyclohexene, 4-(hydroxymethyl)cyclohexene (3), and 5-endo-carboxynorbornene (5), added Ad=Ad does not suppress the reaction completely. In the cases of the 1,omega-alkenols, the reactions appear to exhibit kinetic terms that are greater than first order in alkenol. In these cases, alcohols such as l-pentanol also accelerate the reaction, pointing to the involvement of the hydroxyl group of the second alkenol as a catalytic species. A unifying mechanism consistent with the data that involves two reversibly formed intermediates is presented.
• Neverov, A.A.; Brown, R.S., Canadian Journal of Chemistry, 1994, vol. 72, # 12, p. 2540 - 2544
  作者：Neverov, A.A.、Brown, R.S.

  DOI：——

  日期：——
• SREBNIK, M.;MECHOULAM, R., J. CHEM. SOC. CHEM. COMMUN., 1984, N 16, 1070-1071
  作者：SREBNIK, M.、MECHOULAM, R.

  DOI：——

  日期：——