3,4-Bis-(3-chloro-2-methyl-phenyl)-hexane-2,5-dione | 118988-95-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,4-Bis-(3-chloro-2-methyl-phenyl)-hexane-2,5-dione
• 英文别名: 3,4-Bis(3-chloro-2-methylphenyl)hexane-2,5-dione
• CAS: 118988-95-7
• 化学式: C₂₀H₂₀Cl₂O₂
• 分子量: 363.284
• InChiKey: ZYCMRWWWKLWKIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-Bis-(3-chloro-2-methyl-phenyl)-hexane-2,5-dione 在 磷酸酐 作用下， 以 乙醇 为溶剂， 生成 3,4-bis(3-chloro-2-methylphenyl)-2,5-dimethylfuran
  参考文献：
  名称：

  2,5b，10b，11-四甲基二氢吡喃并[5,6-c]呋喃：第一个呋喃-异退火[14]环戊烯，其抗磁性环电流与母体系统一样强

  摘要：

  反式呋喃基-二甲基二氢py及其母体内部甲基质子的相对化学位移提供了第一个证据，表明这种异退火不会导致显着性降低。

  DOI：

  10.1016/0040-4039(88)85196-7
• 作为产物：
  描述：

  3-氯-2-甲基苯基氯化镁 在 manganese(IV) oxide 、 sodium hydroxide 、 sodium tetrahydroborate 、 jones' reagent 、 mercury(II) diacetate 、 水 作用下， 以 四氢呋喃 、 溶剂黄146 、 丙酮 为溶剂， 反应 22.5h， 生成 3,4-Bis-(3-chloro-2-methyl-phenyl)-hexane-2,5-dione
  参考文献：
  名称：

  Synthesis and Diatropicity of trans-2‘,5‘,10b,10c-Tetramethylfurano[3,4-e]-10b,10c-dihydropyrene. A Valence Isomerization To Form a Novel Isoannulenofuran at the Expense of Two Benzene and One Furan Rings

  摘要：

  The 1, 4-dicarbonyl compound 22 was prepared by an oxidative coupling of the benzyl methyl ketone 19. Dehydration of 22 gave the 3,4-diarylfuran 16 which upon functional group transformations and a subsequent intramolecular cyclization afforded only the anti isomer of the furanothiacyclophane 27. Ring contraction following a Wittig rearrangement-Hofmann elimination sequence led to the isolation of anti furanocyclophanene 15b. Valence isomerization of 15b to the isoannulenofuran 14b could be achieved either photochemically or thermally with 15b as the thermodynamically more stable isomer. Compound 14b was found to exhibit only a very small ring current. The diatropicity of 14b is clearly affected by a weak participation of the oxygen in pi-electron delocalization and a steric effect of its external methyl groups resulting in a deviation from planarity of its molecular periphery. The thermal conversion of 15b to 14b was determined to have a high activation energy of 114 kJ mol(-1). This thermal process, in addition to involving the disruption of jr-electron delocalization in two benzene and one furan rings, is another example of an unsual concerted, symmetry-forbidden reaction.

  DOI：

  10.1021/jo951586o

文献信息

• 2,5b,10b,11-tetramethyldihydropyreno[5,6-c]furan: the first furan-isoannelated [14]annulene that sustains as strong a diamagnetic ring current as the parent system
  作者：Yee-Hing Lai、Pu Chen

  DOI：10.1016/0040-4039(88)85196-7

  日期：1988.1

  Relative chemical shifts of internal methyl protons of trans-furano-dimethyldihydropyrene and its parent provide the first evidence that such an isoannelation does not lead to a significant decrease in diatropicity.

  反式呋喃基-二甲基二氢py及其母体内部甲基质子的相对化学位移提供了第一个证据，表明这种异退火不会导致显着性降低。
• LAI, YEE-HING;CHEN, PU, TETRAHEDRON LETT., 29,(1988) N 28, C. 3483-3486
  作者：LAI, YEE-HING、CHEN, PU

  DOI：——

  日期：——
• Synthesis and Diatropicity of <i>trans</i>-<i>N</i>-Cyclohexyl-2‘,5‘,10b,10c-tetramethyl- pyrrolo[3,4-<i>e</i>]-10b,10c-dihydropyrene. The First Example of an Iso[17]annulenopyrrole
  作者：Yee-Hing Lai、Pu Chen

  DOI：10.1021/jo970430g

  日期：1997.8.1
• Synthesis and Diatropicity of <i>trans</i>-2‘,5‘,10b,10c-Tetramethylfurano[3,4-<i>e</i>]-10b,10c-dihydropyrene. A Valence Isomerization To Form a Novel Isoannulenofuran at the Expense of Two Benzene and One Furan Rings
  作者：Yee-Hing Lai、Pu Chen

  DOI：10.1021/jo951586o

  日期：1996.1.1

  The 1, 4-dicarbonyl compound 22 was prepared by an oxidative coupling of the benzyl methyl ketone 19. Dehydration of 22 gave the 3,4-diarylfuran 16 which upon functional group transformations and a subsequent intramolecular cyclization afforded only the anti isomer of the furanothiacyclophane 27. Ring contraction following a Wittig rearrangement-Hofmann elimination sequence led to the isolation of anti furanocyclophanene 15b. Valence isomerization of 15b to the isoannulenofuran 14b could be achieved either photochemically or thermally with 15b as the thermodynamically more stable isomer. Compound 14b was found to exhibit only a very small ring current. The diatropicity of 14b is clearly affected by a weak participation of the oxygen in pi-electron delocalization and a steric effect of its external methyl groups resulting in a deviation from planarity of its molecular periphery. The thermal conversion of 15b to 14b was determined to have a high activation energy of 114 kJ mol(-1). This thermal process, in addition to involving the disruption of jr-electron delocalization in two benzene and one furan rings, is another example of an unsual concerted, symmetry-forbidden reaction.