1,2-epoxy-1-methyl-1,2,3,4-tetrahydro-naphthalene | 2042-23-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2-epoxy-1-methyl-1,2,3,4-tetrahydro-naphthalene
• 英文别名: 1-Methyl-1,2-epoxy-1,2,3,4-tetrahydro-naphthalin；7b-methyl-2,3-dihydro-1aH-naphtho[1,2-b]oxirene
• CAS: 2042-23-1
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: ZWZDQLOSSZWVCI-UHFFFAOYSA-N

物化性质

• 熔点：
  34-36 °C
• 沸点：
  241.2±9.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-epoxy-1-methyl-1,2,3,4-tetrahydro-naphthalene 在 indium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以87%的产率得到1-甲基-2-四氢萘酮
  参考文献：
  名称：

  Indium(III) Chloride-Promoted Rearrangement of Epoxides: A Selective Synthesis of Substituted Benzylic Aldehydes and Ketones

  摘要：

  A simple and efficient procedure for the rearrangement of substituted epoxides catalyzed by InCl3 has been developed. Aryl-substituted epoxides isomerize with complete regioselectivity to form a single carbonyl compound via cleavage of the benzylic C-O bond. The reactions are simple, fast, and high yielding. This procedure is very mild compared to those catalyzed with BF3 and other Lewis acids and compatible with several acid-sensitive functionalities. This protocol provides a highly selective synthesis of substituted benzylic aldehydes and ketones. However, rearrangement of alkyl-substituted epoxides is not very selective.

  DOI：

  10.1021/jo980793w
• 作为产物：
  描述：

  1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol 在 碳酸氢钠 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 生成 1,2-epoxy-1-methyl-1,2,3,4-tetrahydro-naphthalene
  参考文献：
  名称：

  A concise synthesis of 1-substituted-2-tetralones by selective diol dehydration leading to ketone transposition

  摘要：

  Dehydration of 1-substituted-1,2-tetralindiols with zinc iodide afforded the corresponding 2-tetralones in excellent yields. This procedure was found to be superior to the more conventional BF3-catalyzed rearrangement of 1-substituted-1,2-epoxytetralins. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01014-5

文献信息

• A partially water-soluble cationic Mn(III)–salphen complex for catalytic epoxidation
  作者：Amir Abdolmaleki、Saeed Malek-Ahmadi

  DOI：10.1139/v11-094

  日期：2011.10

  Synthesis and application of new cationic Mn(III)–salphen complexes for catalytic epoxidation of olefins to epoxides in a homogeneous reaction media have been reported. The experimental data showed that the cationic salphen is more active than its neutral form. The acceleration of the reaction rate is attributed to the phase-transfer capability of the built-in phenazinium salt of the Mn(III)–salphen catalyst.

  报道了新的阳离子Mn(III)-salphen配合物的合成和应用，用于催化烯烃在均相反应介质中氧化成环氧化物。实验数据显示，阳离子salphen比其中性形式更活跃。反应速率的加快归因于Mn(III)-salphen催化剂内置的苯并啉盐的相转移能力。
• Indium(III) Chloride-Promoted Rearrangement of Epoxides: A Selective Synthesis of Substituted Benzylic Aldehydes and Ketones
  作者：Brindaban C. Ranu、Umasish Jana

  DOI：10.1021/jo980793w

  日期：1998.11.1

  A simple and efficient procedure for the rearrangement of substituted epoxides catalyzed by InCl3 has been developed. Aryl-substituted epoxides isomerize with complete regioselectivity to form a single carbonyl compound via cleavage of the benzylic C-O bond. The reactions are simple, fast, and high yielding. This procedure is very mild compared to those catalyzed with BF3 and other Lewis acids and compatible with several acid-sensitive functionalities. This protocol provides a highly selective synthesis of substituted benzylic aldehydes and ketones. However, rearrangement of alkyl-substituted epoxides is not very selective.
• Effect of ring size and methyl substituents on lithium bromide-catalyzed rearrangements of aryloxiranes
  作者：Harold Banks、Herman Ziffer

  DOI：10.1021/jo00140a029

  日期：1982.9
• MARSALL P. A.; PRAGER R. H., AUSTRAL. J. CHEM., 1979, 32, NO 6, 1261-1271
  作者：MARSALL P. A.、 PRAGER R. H.

  DOI：——

  日期：——
• BANKS, H.;ZIFFER, H., J. ORG. CHEM., 1982, 47, N 19, 2743-3747
  作者：BANKS, H.、ZIFFER, H.

  DOI：——

  日期：——