1,1-dibenzyl-1,4-dihydronaphthalene | 120651-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1-dibenzyl-1,4-dihydronaphthalene
• 英文别名: Naphthalene, 1,4-dihydro-1,1-bis(phenylmethyl)-；4,4-dibenzyl-1H-naphthalene
• CAS: 120651-56-1
• 化学式: C₂₄H₂₂
• 分子量: 310.439
• InChiKey: JRTHMTQLEPGGIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  443.7±25.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,1-dibenzyl-1,4-dihydronaphthalene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以89%的产率得到1-Benzyl-naphthalene
  参考文献：
  名称：

  Novel rearrangement and cyclization processes resulting from bromination of 1,1-dibenzyltetralin derivatives

  摘要：

  Addition of bromine to hydrocarbon 1 results in an aromatic alkylation to form the bicyclo[3.3.1]nonane derivative 5. Addition of bromine to ketone 3 in acetonitrile solution results in a dienone-phenol rearrangement to form phenol 6, while reaction of ketone 4 with phosphorus pentabromide yields phenols 10 and 11. This reaction results from a novel ''bromo ketone-phenol'' rearrangement, as demonstrated by the fact that bromo ketones 12 and 13 spontaneously isomerize to 10 and 11.

  DOI：

  10.1021/jo00032a015
• 作为产物：
  描述：

  1,1-dibenzyl-3,4-dihydro-2(1H)-naphthalenone p-toluenesulfonylhydrazone 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1,1-dibenzyl-1,4-dihydronaphthalene
  参考文献：
  名称：

  Shi, Xiaolian; Day, Roberta; Miller, Bernard, Journal of the Chemical Society. Perkin transactions I, 1989, p. 1166 - 1167

  摘要：

  DOI：

文献信息

• The bromoketone - phenol rearrangement
  作者：Bernard Miller、Xiaolian Shi

  DOI：10.1016/s0040-4039(00)80689-9

  日期：1988.1

  Reaction of ketone with phosphorus pentabromide or bromine results in bromination (or dibromination) at C-4. The resulting α-bromoketones rearrange rapidly in acid solutions to yield phenols and .

  酮与五溴化磷或溴的反应导致C-4处的溴化（或二溴化）。所得的α-溴代酮在酸性溶液中迅速重排，生成酚和。
• Unusual regiochemistry in the hydroboration of 3,3-dibenzylcycloalkenes
  作者：Xiaolian Shi、Bernard Miller

  DOI：10.1016/s0040-4039(00)76516-6

  日期：1994.1

  Reaction of 3,3-dibenzylcycloalkenes with diborane results in predominant attack by boron at the more crowded ends of the double bonds.
• MILLER, BERNARD;SHI, XIAOLIAN, TETRAHEDRON LETT., 29,(1988) N 40, C. 5099-5100
  作者：MILLER, BERNARD、SHI, XIAOLIAN

  DOI：——

  日期：——
• Shi, Xiaolian; Day, Roberta; Miller, Bernard, Journal of the Chemical Society. Perkin transactions I, 1989, p. 1166 - 1167
  作者：Shi, Xiaolian、Day, Roberta、Miller, Bernard

  DOI：——

  日期：——
• Novel rearrangement and cyclization processes resulting from bromination of 1,1-dibenzyltetralin derivatives
  作者：Bernard Miller、Xiaolian Shi

  DOI：10.1021/jo00032a015

  日期：1992.3

  Addition of bromine to hydrocarbon 1 results in an aromatic alkylation to form the bicyclo[3.3.1]nonane derivative 5. Addition of bromine to ketone 3 in acetonitrile solution results in a dienone-phenol rearrangement to form phenol 6, while reaction of ketone 4 with phosphorus pentabromide yields phenols 10 and 11. This reaction results from a novel ''bromo ketone-phenol'' rearrangement, as demonstrated by the fact that bromo ketones 12 and 13 spontaneously isomerize to 10 and 11.