1-(3,4-Dihydronaphthalen-1-yl)-2-methylpropan-2-ol | 940868-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(3,4-Dihydronaphthalen-1-yl)-2-methylpropan-2-ol
• 英文别名: 1-(3,4-dihydronaphthalen-1-yl)-2-methylpropan-2-ol
• CAS: 940868-74-6
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: IIHFOOZKHUCARX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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-(3,4-Dihydronaphthalen-1-yl)-2-methylpropan-2-ol 、 苯甲醛 在 碘 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 2,2-dimethyl-4-phenyl-2,4,5,6-tetrahydro-1H-benzo[f]isochromene 、 (4SR,4aSR)-2,2-dimethyl-4-phenyl-4,4a,5,6-tetrahydro-2H-benzo[f]isochromene
  参考文献：
  名称：

  An expeditious synthesis of hexahydrobenzo[f]isochromenes and of hexahydrobenzo[f]isoquinoline via iodine-catalyzed Prins and aza-Prins cyclization

  摘要：

  Homoallylic alcohols (primary, secondary, or tertiary containing an endocyclic or an exocyclic double bond) react with equimolar amounts of aldehydes (aliphatic or aromatic) and ketones (aliphatic) in the presence of 5 mol % of iodine. This Prins cyclization was used in the preparation of hexahydrobenzo[f]isochromenes and of a 4-hydroxy-tetrahydropyran, in 54-81% yield. The procedure is also efficient for an aza-Prins cyclization of a homoallylic sulfonamide and benzaldehyde, producing a hexahydrobenzo[f]isoquinoline. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.202

文献信息

• Iodine-Catalyzed Prins Cyclization of Homoallylic Alcohols and Aldehydes
  作者：Kachi Reddy、Iara Rosa、Antônio Doriguetto、Erick Bastos、Luiz Silva

  DOI：10.3390/molecules180911100

  日期：——

  The iodine-catalyzed Prins cyclization of homoallylic alcohols and aldehydes was investigated under metal-free conditions and without additives. Anhydrous conditions and inert atmosphere are not required. The reaction of 2-(3,4-dihydronaphthalen-1-yl)propan-1-ol and 21 aldehydes (aliphatic and aromatic) in CH2Cl2 in the presence of 5 mol % of iodine gave 1,4,5,6-tetrahydro-2H-benzo[f]isochromenes in 54%–86% yield. Under similar conditions, the Prins cyclization of six alcohols containing an endocyclic double bond (primary, secondary, or tertiary) led to dihydropyrans in 52%–91% yield. The acyclic homoallylic alcohols gave 4-iodo-tetrahydropyran in 29%–41% yield in the presence of 50 mol % of iodine. This type of substrate is the main limitation of the methodology. The relative configuration of the products was assigned by NMR and X-ray analysis. The mechanism and the ratio of the products are discussed, based on DFT calculations.

  在无金属和无添加剂的条件下研究了碘催化的高烯丙醇和醛的 Prins 环化。不需要无水条件和惰性气氛。 2-(3,4-二氢萘-1-基)丙-1-醇和 21 种醛（脂肪族和芳香族）在 CH2Cl2 中在 5 mol% 碘存在下反应，得到 1,4,5,6-四氢-2H-苯并[f]异色烯，产率 54%–86%。在类似条件下，六种含有环内双键（伯键、仲键或叔键）的醇进行 Prins 环化，生成二氢吡喃，产率为 52%–91%。在 50 mol % 的碘存在下，无环高烯丙醇以 29%–41% 的产率生成 4-碘-四氢吡喃。这种类型的底物是该方法的主要限制。通过NMR和X射线分析确定了产物的相对构型。基于DFT计算，讨论了机理和产物的比例。
• An expeditious synthesis of hexahydrobenzo[f]isochromenes and of hexahydrobenzo[f]isoquinoline via iodine-catalyzed Prins and aza-Prins cyclization
  作者：Luiz F. Silva、Samir A. Quintiliano

  DOI：10.1016/j.tetlet.2009.02.202

  日期：2009.5

  Homoallylic alcohols (primary, secondary, or tertiary containing an endocyclic or an exocyclic double bond) react with equimolar amounts of aldehydes (aliphatic or aromatic) and ketones (aliphatic) in the presence of 5 mol % of iodine. This Prins cyclization was used in the preparation of hexahydrobenzo[f]isochromenes and of a 4-hydroxy-tetrahydropyran, in 54-81% yield. The procedure is also efficient for an aza-Prins cyclization of a homoallylic sulfonamide and benzaldehyde, producing a hexahydrobenzo[f]isoquinoline. (C) 2009 Elsevier Ltd. All rights reserved.