1-(3-buten-1-yl)-2-cyclohexen-1-ol | 158847-63-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-buten-1-yl)-2-cyclohexen-1-ol
• 英文别名: 1-But-3-enylcyclohex-2-en-1-ol
• CAS: 158847-63-3
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: ARLYKSVKLQVTPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-buten-1-yl)-2-cyclohexen-1-ol 在 正丁基锂 、 zirconocene dichloride 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 24.0h， 以40%的产率得到(1R,3aS,7aR)-1-Methyl-octahydro-inden-3a-ol
  参考文献：
  名称：

  Stereoselectivity in Intramolecular Diene Cyclozirconation: A Combined Experimental and Theoretical Approach

  摘要：

  Intramolecular diene cyclozirconation (1 --> 2 + 3 --> 4) can be highly diastereoselective (97:3 trans/cis for 4). It is suggested that the cis and trans diastereomers of the zirconacycle are equilibrating under the conditions of the reaction, and that the observed diastereomeric preference of 4 reflects the relative stability of the two diastereomeric zirconacycles. Results for the intramolecular cyclozirconation of two other dienes, 8 and 14, as well as for the ''heterodiene'' N,N-diallylaniline are also reported. Computational results at the molecular mechanics, semiempirical molecular orbital ZINDO and nonlocal density functional theory levels are used to explain the observed stereochemistry in terms of thermodynamic and kinetic control.

  DOI：

  10.1021/ja00100a007
• 作为产物：
  描述：

  、 2-环己烯-1-酮 生成 1-(3-buten-1-yl)-2-cyclohexen-1-ol
  参考文献：
  名称：

  KOZIMA, SINPEI;ISHII, TOSHIYUKI;TSUBOI, TAKASHI;KAWANISI, MITUYOSI;MIZUNO+, CHEM. EXPRESS, 2,(1987) N 5, 301-304

  摘要：

  DOI：

文献信息

• An improved procedure for the synthesis of allylic spiro-γ-lactones
  作者：Jagattaran Das、Prabir K. Choudhury、Srinivasan Chandrasekaran

  DOI：10.1016/0040-4020(95)00067-i

  日期：1995.3

  Allylic spiro-γ-lactones of the type 4 have been synthesised in two steps starting from the carbonyl precursors using heterogeneous permanganate oxidation as the key step.

  使用异质高锰酸盐氧化作为关键步骤，从羰基前体开始，分两步合成了4型烯丙基螺-γ-内酯。
• Enantioselective Cu-Catalyzed 1,4-Addition of Grignard Reagents to Cyclohexenone Using Taddol-Derived Phosphine-Phosphite Ligands and 2-Methyl-THF as a Solvent
  作者：Tobias Robert、Janna Velder、Hans-Günther Schmalz

  DOI：10.1002/anie.200803247

  日期：2008.9.22
• KOZIMA, SINPEI;ISHII, TOSHIYUKI;TSUBOI, TAKASHI;KAWANISI, MITUYOSI;MIZUNO+, CHEM. EXPRESS, 2,(1987) N 5, 301-304
  作者：KOZIMA, SINPEI、ISHII, TOSHIYUKI、TSUBOI, TAKASHI、KAWANISI, MITUYOSI、MIZUNO+

  DOI：——

  日期：——
• Stereoselectivity in Intramolecular Diene Cyclozirconation: A Combined Experimental and Theoretical Approach
  作者：Douglass F. Taber、James P. Louey、Yanong Wang、William A. Nugent、David A. Dixon、Richard L. Harlow

  DOI：10.1021/ja00100a007

  日期：1994.10

  Intramolecular diene cyclozirconation (1 --> 2 + 3 --> 4) can be highly diastereoselective (97:3 trans/cis for 4). It is suggested that the cis and trans diastereomers of the zirconacycle are equilibrating under the conditions of the reaction, and that the observed diastereomeric preference of 4 reflects the relative stability of the two diastereomeric zirconacycles. Results for the intramolecular cyclozirconation of two other dienes, 8 and 14, as well as for the ''heterodiene'' N,N-diallylaniline are also reported. Computational results at the molecular mechanics, semiempirical molecular orbital ZINDO and nonlocal density functional theory levels are used to explain the observed stereochemistry in terms of thermodynamic and kinetic control.