亚乙烯基三环[3.3.1.13,7]癸烷 | 59556-21-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 亚乙烯基三环[3.3.1.13,7]癸烷
• 英文名称: Ethenylidenetricyclo<3.3.1.1^3,7>decane
• 英文别名: vinylideneadamantane；2-vinylidene-adamantane；Vinylidenadamantan；2-Ethenylideneadamantane
• CAS: 59556-21-7
• 化学式: C₁₂H₁₆
• 分子量: 160.259
• InChiKey: DXARRWRGWTYQPG-UHFFFAOYSA-N

物化性质

• 沸点：
  237.7±7.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  亚乙烯基三环[3.3.1.13,7]癸烷 以16%的产率得到
  参考文献：
  名称：

  SASAKI T.; EGUCHI S.; HIRAKO Y., TETRAHEDRON LETT. , 1976, NO 7, 541-544

  摘要：

  DOI：
• 作为产物：
  描述：

  3'-methylenespiro-4'-one 400.0 ℃ 、13.33 Pa 条件下， 以91%的产率得到亚乙烯基三环[3.3.1.13,7]癸烷
  参考文献：
  名称：

  .alpha.-Methylene .beta.-lactones as masked allenes and allene equivalents: some selected chemical transformations

  摘要：

  Selective chemical transformations have been performed on a number of alpha-methylene beta-lactones to illustrate that these highly functionalized heterocycles serve as useful building blocks in organic synthesis. Thus, thermal decarboxylation of these ''masked allenes'' provides a useful regioselective preparation of allenes with a predetermined substitution pattern. Nucleophilic addition takes place at the carbonyl group with ring opening, but free-radical addition, e.g., thiophenol, and electrophilic addition, e.g., bromine, proceed at the exomethylene group with preservation of the beta-lactone ring. [4 + 2] Cycloaddition with cyclopentadiene affords the expected beta-lactones, which on thermal decarboxylation lead to 2-alkylidenenorbornenes. This regio- and stereoselective transformation establishes the alpha-methylene beta-lactones as valuable allene equivalents. The alpha-methylene beta-lactones serve also as dipolarophiles by undergoing readily 1,3-dipolar cycloaddition with diazoalkanes. Reaction with Lawesson's reagent affords a hitherto unknown alpha-methylene beta-(S)-lactone.

  DOI：

  10.1021/jo00020a017

文献信息

• A 3-Methylene-1,2-dioxetane as a Possible Chemiluminescent Intermediate in Singlet Oxygenation of Allene
  作者：Takeshi Akasaka、Koichiro Fukuoka、Wataru Ando

  DOI：10.1246/bcsj.62.1367

  日期：1989.4.15

  Photosensitized oxygenation of bis(adamantylidene)methane and vinylideneadamantane at −78 °C afforded adamantanone and the former also emitted light when warmed up to room temperature in the presence of a fluorescer. A 3-methylene-1,2-dioxetane as a possible chemiluminescent intermediate is proposed.

  双（金刚烷基）甲烷和亚乙烯基金刚烷在 -78°C 下的光敏氧化得到金刚烷酮，当在荧光剂存在下加热至室温时，前者也会发光。建议使用 3-亚甲基-1,2-二氧杂环丁烷作为可能的化学发光中间体。
• Kostikov, R. R.; Grishina, E. N.; Slobodin, Ya. M., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1298 - 1306
  作者：Kostikov, R. R.、Grishina, E. N.、Slobodin, Ya. M.

  DOI：——

  日期：——
• Synthesis and some reactions of vinylideneadamantane
  作者：Tadashi Sasaki、Shoji Eguchi、Yoshiyuki Hirako

  DOI：10.1016/s0040-4039(00)77905-6

  日期：1976.2
• KOSTIKOV, R. R.;GRISHINA, E. N.;SLOBODIN, YA. M., ZH. ORGAN. XIMII, 1984, 20, N 7, 1426-1435
  作者：KOSTIKOV, R. R.、GRISHINA, E. N.、SLOBODIN, YA. M.

  DOI：——

  日期：——