6,7-Dichloro-1,4-dihydro-1,4-epoxynaphthalene | 144474-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,7-Dichloro-1,4-dihydro-1,4-epoxynaphthalene
• 英文别名: 4,5-Dichloro-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene
• CAS: 144474-60-2
• 化学式: C₁₀H₆Cl₂O
• 分子量: 213.063
• InChiKey: RXQBHQQIDRPOON-UHFFFAOYSA-N

物化性质

• 沸点：
  293.4±40.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  呋喃 、 6,7-Dichloro-1,4-dihydro-1,4-epoxynaphthalene 在 sodium amide 作用下， 生成 (+/-)-anti-9-Chloro-1,4,5,8-tetrahydro-1,4,5,8-diepoxyphenanthrene 、 (+/-)-syn-9-Chloro-1,4,5,8-tetrahydro-1,4,5,8-diepoxyphenanthrene
  参考文献：
  名称：

  从多卤代苯的区域选择性生成芳烃。合成的合成正和反-1,4,5,8,9,12-六氢-1,4：5,8：9,12-三环氧联苯

  摘要：

  卤代苯1,2,4,5-四溴苯6，六溴苯9，对二氯四溴苯11和1,2-二溴-4,5-二氯苯12被研究为1,3-bis-，1,4 -双-和1,3,5-三-芳烃前体，使用烷基锂和碱金属酰胺作为金属化试剂。芳烃以呋喃为二烯被困在Diels-Alder反应中。现在可以容易地分两步获得标题化合物3a / b，其从1,2,4,5-四溴苯6的总收率为7％。

  DOI：

  10.1016/s0040-4020(01)89874-4
• 作为产物：
  描述：

  2,4,5-三氯苯胺 在 三氢化镧 、 硫酸 、 碘 、 溶剂黄146 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 5.67h， 生成 6,7-Dichloro-1,4-dihydro-1,4-epoxynaphthalene
  参考文献：
  名称：

  Dehalogenation of o-dihalogen substituted arenes and α,α′-dihalogen substituted o-xylenes with lanthanum metal

  摘要：

  It was found that lanthanum metal caused the dehalogenation of o-dihalogen substituted arenes and alpha,alpha'-dihalogen substituted o-xylenes to generate the corresponding benzynes and o-quinodimethanes. When o-dihalogen substituted arenes were allowed to react with lanthanum metal in the presence of dienes, the Diels-Alder products between benzyne and dienes were formed in moderate to good yields. Similarly, the Diels-Alder adducts of o-quinodimethane with dienophiles were obtained, in the reaction of alpha,alpha'-dibromo-o-xylenes with lanthanum metal in the presence of dienophiles. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01027-5

文献信息

• Reaction of 1,2-dihalogen substituted arenes with lanthanum metal: a new generation method of benzyne
  作者：Hiroshi Kawabata、Toshiki Nishino、Yutaka Nishiyama、Noboru Sonoda

  DOI：10.1016/s0040-4039(02)00958-9

  日期：2002.7

  A new generation method of benzyne has been developed. When 1,2-dihalogen substituted arenes were allowed to react with lanthanum metal in the presence of dienes, Diels–Alder products between benzyne and dienes were formed in moderate to good yields.

  已经开发了新一代的苯甲醛方法。当在二烯存在下使1,2-二卤素取代的芳烃与镧金属反应时，苯并炔和二烯之间的狄尔斯-阿尔德产物形成的产率中等至良好。
• The regioselective generation of arynes from polyhalogenobenzenes. An improved synthesis of syn- and anti-1,4,5,8,9,12-hexahydro-1,4:5,8:9,12-triepoxytriphenylene
  作者：Françisco Raymo、Franz H. Kohnke、Francesca Cardullo、Ulrich Girreser、J.Fraser Stoddart

  DOI：10.1016/s0040-4020(01)89874-4

  日期：1992.1

  5-dichlorobenzene 12, were investigated as 1,3-bis-, 1,4-bis-, and 1,3,5-tris-aryne precursors by using alkyllithiums and alkali metal amides as the metalating reagents. The arynes were trapped in Diels-Alder reactions with furan as the diene. The title compounds 3a/b are now readily available in two steps in 7% overall yield from 1,2,4,5-tetrabromobenzene 6.

  卤代苯1,2,4,5-四溴苯6，六溴苯9，对二氯四溴苯11和1,2-二溴-4,5-二氯苯12被研究为1,3-bis-，1,4 -双-和1,3,5-三-芳烃前体，使用烷基锂和碱金属酰胺作为金属化试剂。芳烃以呋喃为二烯被困在Diels-Alder反应中。现在可以容易地分两步获得标题化合物3a / b，其从1,2,4,5-四溴苯6的总收率为7％。
• Dehalogenation of o-dihalogen substituted arenes and α,α′-dihalogen substituted o-xylenes with lanthanum metal
  作者：Yutaka Nishiyama、Hiroshi Kawabata、Toshiki Nishino、Kouji Hashimoto、Noboru Sonoda

  DOI：10.1016/s0040-4020(03)01027-5

  日期：2003.8

  It was found that lanthanum metal caused the dehalogenation of o-dihalogen substituted arenes and alpha,alpha'-dihalogen substituted o-xylenes to generate the corresponding benzynes and o-quinodimethanes. When o-dihalogen substituted arenes were allowed to react with lanthanum metal in the presence of dienes, the Diels-Alder products between benzyne and dienes were formed in moderate to good yields. Similarly, the Diels-Alder adducts of o-quinodimethane with dienophiles were obtained, in the reaction of alpha,alpha'-dibromo-o-xylenes with lanthanum metal in the presence of dienophiles. (C) 2003 Elsevier Ltd. All rights reserved.