1,1'-(1,4-丁烷二基)二环戊烷 | 2980-70-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 饱和烃
• 中文名称: 1,1'-(1,4-丁烷二基)二环戊烷
• 英文名称: 1,4-dicyclopentylbutane
• 英文别名: 1,4-dicyclopentyl-butane；1,4-Dicyclopentyl-butan；1,1'-(1,4-butanediyl)bis-cyclopentane；1,4-Bis-cyclopentyl-butan；1.4-(Dicyclopentyl)-butan；Butane, 1,4-dicyclopentyl-；4-cyclopentylbutylcyclopentane
• CAS: 2980-70-3
• 化学式: C₁₄H₂₆
• mdl: MFCD09038374
• 分子量: 194.36
• InChiKey: DDFOSKBMELVNDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  6-羟基环癸烷-1-酮 在 Pt-oxide 4-二甲氨基吡啶 、 TiCl₃-1,2-dimethoxyethane 、 4 A molecular sieve 、 氢气 、 sodium acetate 、 铜 、 magnesium 、 三乙胺 、 pyridinium chlorochromate 、 锌 作用下， 以 乙二醇二甲醚 、 乙醚 、 二氯甲烷 为溶剂， 反应 72.17h， 生成 1,1'-(1,4-丁烷二基)二环戊烷
  参考文献：
  名称：

  Concerning attempts to synthesize out-bicyclo[4.4.4]tetradec-1-ene derivatives

  摘要：

  The keto aldehydes 4-[6-oxo-1-(tetrahydropyranyloxy)cyclodecyl]butanal (17), (E)-4-(6-oxocyclodec-1-enyl)butanal (24), and 4-(6-oxocyclodecylidene)butanal (7) have been synthesized. No bicyclo[4.4.4]tetradecadienes were found in the products from the zero-valent titanium reductive cyclization of compound 24. Instead, products arising from transannular reactions of the cyclodecyl ring system were isolated. 1,6-Divinylbicyclo[4.4.0]decane (32) was obtained from the reductive cyclization of keto enal 7. The most plausible route for its formation is through a Cope rearrangement of a bicyclo[4.4.4]tetradecene derivative, suggesting that an out-bicyclo[4.4.4]tetradecenylbistitanium pinacolate 8 intervened.

  DOI：

  10.1021/jo00052a024

文献信息

• Exceptionally high decarboxylation rate of a primary aliphatic acyloxy radical determined by radical product yield analysis and quantitative ¹ H-CIDNP spectroscopy
  作者：Alicia Fraind、Ryan Turncliff、Teri Fox、Justin Sodano、Lev R. Ryzhkov

  DOI：10.1002/poc.1836

  日期：2011.9

  Symmetrical (RCO2CO2R; R = XCH2CH2) and asymmetrical (RCO2CO2R′; R = C9H19CH2CH2, R′ = CH3 or m‐ClC6H4) primary diacyl peroxides were thermally decomposed under different conditions to analyze the decarboxylation rates of the thermally generated acyloxy radicals. Quantitative models of the geminate product yields, and qualitative and quantitative 1H‐CIDNP spectroscopy were used to obtain the decarboxylation

  对称的（RCO 2 CO 2 R; R = XCH 2 CH 2）和不对称的（RCO 2 CO 2 R'; R = C 9 H 19 CH 2 CH 2，R'= CH 3或m- ClC 6 H 4）在不同条件下对二酰基过氧化物进行热分解，以分析热生成的酰氧基的脱羧速率。萌芽产品产量的定量模型，以及定性和定量1H-CIDNP光谱用于获得脱羧速率的估计值。此处报告的结果表明，与短链酰氧基自由基（如丙酰氧基）不同，长链酰氧基自由基具有所有已知酰氧基自由基的最高脱羧速率，估计在80至140°C之间为（0.5–1.5）×10 12  s -1。考虑到酰氧基自由基的解离态的性质，这种速率似乎是长链取代基的空间体积使前者不稳定的结果。另外，该数量级的速率表明伯二酰基过氧化物的几乎一致的脱羧作用。版权所有©2011 John Wiley＆Sons，Ltd.
• Plate; Stanko, Doklady Akademii Nauk SSSR, 1957, vol. 114, p. 339,341
  作者：Plate、Stanko

  DOI：——

  日期：——
• Nogaideli,A.I.; Gonadze,G.M., Journal of general chemistry of the USSR, 1961, vol. 31, p. 1718 - 1722
  作者：Nogaideli,A.I.、Gonadze,G.M.

  DOI：——

  日期：——
• Concerning attempts to synthesize out-bicyclo[4.4.4]tetradec-1-ene derivatives
  作者：David P. G. Hamon、Guy Y. Krippner

  DOI：10.1021/jo00052a024

  日期：1992.12

  The keto aldehydes 4-[6-oxo-1-(tetrahydropyranyloxy)cyclodecyl]butanal (17), (E)-4-(6-oxocyclodec-1-enyl)butanal (24), and 4-(6-oxocyclodecylidene)butanal (7) have been synthesized. No bicyclo[4.4.4]tetradecadienes were found in the products from the zero-valent titanium reductive cyclization of compound 24. Instead, products arising from transannular reactions of the cyclodecyl ring system were isolated. 1,6-Divinylbicyclo[4.4.0]decane (32) was obtained from the reductive cyclization of keto enal 7. The most plausible route for its formation is through a Cope rearrangement of a bicyclo[4.4.4]tetradecene derivative, suggesting that an out-bicyclo[4.4.4]tetradecenylbistitanium pinacolate 8 intervened.