1-Benzyloxy-penten-(3)-ol-(2) | 14869-02-4

• 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: 1-Benzyloxy-penten-(3)-ol-(2)
• 英文别名: 1-(Phenylmethoxy)-3-penten-2-ol；1-phenylmethoxypent-3-en-2-ol
• CAS: 14869-02-4
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: VGJQTCINOXITIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (2RS,3RS)-4-(benzyloxy)-2,3-epoxybutan-1-al 在 zirconocene hydrochloride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 1-Benzyloxy-penten-(3)-ol-(2)
  参考文献：
  名称：

  Hydrozirconation of alkenyloxirane derivatives: Preparation of cycloalkylmethanols

  摘要：

  Cyclopentyl and cyclopropylmethanol derivatives were efficiently prepared through a chemoselective hydrozirconation reaction of (1-butenyl)oxirane and vinyloxirane with Cp2ZrHCl. However, the attemped reaction of (1-pentenyl)oxirane or (1-propenyl)oxirane failed to yield cyclohexyl or cyclobutylmethanols. The ring formation was stereospecific and proceeded with the inversion of the configuration at the reacting oxirane carbon. The origin of stereospecificity and the stereoselectivity in the formation of cyclopropylmethanols was presumed by the approach of the Schwartz reagent from the less hindered site of the stable gauche-conformer of the vinyloxirane compound in the transition state. (Cyclopropylmethyl)amine derivatives were also prepared by the treatment of vinylaziridine derivatives with Cp2ZrHCl. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10340-4

文献信息

• Formation of cyclopropyl carbinols through a highly diastereoselective hydrozirconation of vinyloxirane derivatives
  作者：Susumu Harada、Noboru Kowase、Takeo Taguchi、Yuji Hanzawa

  DOI：10.1016/s0040-4039(97)00233-5

  日期：1997.3

  Cyclopropyl carbinol derivatives were efficiently prepared through a highly diastereoselective hydrozirconation of vinyloxirones and the intramolecular nucleophilic attack of the generated alkylzirconocene with the inversion of the configuration at the reacting oxirane carbon.

  环丙基甲醇衍生物可通过乙烯基氧杂环丁烷的高度非对映选择性加氢锆化反应以及生成的烷基锆茂茂的分子内亲核攻击以及在环氧乙烷碳原子上构型的反转而有效地制备。
• Castro,B., Bulletin de la Societe Chimique de France, 1967, p. 1540 - 1547
  作者：Castro,B.

  DOI：——

  日期：——