1,6,8,10-tetramethylheptalene-4,5-dicarbaldehyde | 172266-39-6

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: 1,6,8,10-tetramethylheptalene-4,5-dicarbaldehyde
• 英文别名: 5,6,8,10-Tetramethylheptalene-1,2-dicarbaldehyde
• CAS: 172266-39-6
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: CABFXVGARYKIEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  磷酰基乙酸三乙酯 、 1,6,8,10-tetramethylheptalene-4,5-dicarbaldehyde 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 37.0h， 以86%的产率得到diethyl 5,6,8,10-tetramethylheptalene-1,2-bis[prop-2-enoate]
  参考文献：
  名称：

  Synthesis of Benzo[a]heptalenes via Benzanellation–Aromatization Sequence

  摘要：

  A novel approach towards the synthesis of functionalized benzo[a]heptalenes 9 and 10 via a 6 6pi-electrocyclic ring closure - aromatization sequence of corresponding bis[prop-2-enoates] 5 and 6 has been developed (Scheme 1). The starting bis[prop-2-enoates] have been prepared from the corresponding dialdehydes 3a and 4a in a Wittig-Horner reaction, and their UV/VIS properties have also been investigated (Fig. I and Table 1). The dehydrogenations of the corresponding diols I and 2 to dialdehydes with a number of oxidizing reagents, including MnO2 in CH2Cl2, tetrapropylammonium perruthenate (TPAP), and activated DMSO, have been studied in detail.

  DOI：

  10.1002/1522-2675(200204)85:4<1128::aid-hlca1128>3.0.co;2-q
• 作为产物：
  描述：

  1,6,8,10-tetramethylheptalene-4,5-dimethanol 在 草酰氯 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 5.0h， 以15%的产率得到10-(chloromethylidene)-6,10-dihydro-5-methylidene-1,6,8-trimethylheptalene-4-carbaldehyde
  参考文献：
  名称：

  Synthesis of Benzo[a]heptalenes via Benzanellation–Aromatization Sequence

  摘要：

  A novel approach towards the synthesis of functionalized benzo[a]heptalenes 9 and 10 via a 6 6pi-electrocyclic ring closure - aromatization sequence of corresponding bis[prop-2-enoates] 5 and 6 has been developed (Scheme 1). The starting bis[prop-2-enoates] have been prepared from the corresponding dialdehydes 3a and 4a in a Wittig-Horner reaction, and their UV/VIS properties have also been investigated (Fig. I and Table 1). The dehydrogenations of the corresponding diols I and 2 to dialdehydes with a number of oxidizing reagents, including MnO2 in CH2Cl2, tetrapropylammonium perruthenate (TPAP), and activated DMSO, have been studied in detail.

  DOI：

  10.1002/1522-2675(200204)85:4<1128::aid-hlca1128>3.0.co;2-q

文献信息

• Formation of Heptaleno[1,2-c]furans and Heptaleno[1,2-c]furanones
  作者：Peter Uebelhart、Peter Mohler、Reza-Ali Fallahpour、Hans-J�rgen Hansen

  DOI：10.1002/hlca.19950780605

  日期：1995.9.20

  into their antipodes on a Chiralcel OD column. The (P)-configuration is assigned to the heptaleno[1,2-c]furans showing a negative Cotton effect at ca. 320 nm in the CD spectrum in hexane (cf. Figs. 3–5 as well as Table 7). The (P)-configuration of (–)-6a is correlated with the established (P)-configuration of the dimethanol (–)-5avia dehydrogenation with MnO2. The degree of twisting of the heptalene

  庚烷-4,5-二甲醇4a和4d的脱氢反应在室温下与碱性MnO 2在室温下的CH 2 Cl 2中不经历双键转移（DBS）过程，导致分别形成相应的庚二酮[1,2- c ]呋喃6a和6d，以及分别形成相应的庚二酮[1,2 - c ]呋喃-3-酮7a和7d（参见方案2和8）。两种产品类型的形成必然涉及DBS流程（请参阅方案7）。的DBS异构体的脱氢反应4a中，即，图5a，具有的MnO 2在CH 2氯2在室温下的结果，除了图6A和7A，在heptaleno [1,2的形成Ç ] -furan- 1-酮8a和少量的庚烯-4,5-二甲醛9a（参见方案3）。在CH 2 Cl中用MnO 2脱氢时，具有庚烯骨架CC键固定位置的苯并[ a ]庚二烯-6,7-二甲醇4c在图2中，仅给出相应的呋喃酮11b（方案4）。由[ 2 ħ 2 ]在C（7）的甲醇函数的-labelling，它可以表明，呋喃酮的形成发生在相应的乳醇的阶段[3-
• Synthesis of Benzo[a]heptalenes via Benzanellation–Aromatization Sequence
  作者：Ekaterina A. Ochertyanova、Hans-Jürgen Hansen

  DOI：10.1002/1522-2675(200204)85:4<1128::aid-hlca1128>3.0.co;2-q

  日期：2002.4

  A novel approach towards the synthesis of functionalized benzo[a]heptalenes 9 and 10 via a 6 6pi-electrocyclic ring closure - aromatization sequence of corresponding bis[prop-2-enoates] 5 and 6 has been developed (Scheme 1). The starting bis[prop-2-enoates] have been prepared from the corresponding dialdehydes 3a and 4a in a Wittig-Horner reaction, and their UV/VIS properties have also been investigated (Fig. I and Table 1). The dehydrogenations of the corresponding diols I and 2 to dialdehydes with a number of oxidizing reagents, including MnO2 in CH2Cl2, tetrapropylammonium perruthenate (TPAP), and activated DMSO, have been studied in detail.