methylenecyclodecane | 3817-57-0

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: methylenecyclodecane
• 英文别名: Methenylcyclodecane；Methylen-cyclodecan；Methylencyclodecan；methylidenecyclodecane
• CAS: 3817-57-0
• 化学式: C₁₁H₂₀
• 分子量: 152.28
• InChiKey: DHNLLZWVLDZCFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902199090

反应信息

• 作为反应物：
  描述：

  methylenecyclodecane 在 过氧化氢苯甲酰 作用下， 以 氯仿 为溶剂， 生成 cyclodecanylcarboxaldehyde
  参考文献：
  名称：

  Addition Reactions with Methylenecyclodecane^1a,b

  摘要：

  DOI：

  10.1021/jo01056a049
• 作为产物：
  描述：

  N,N-Dimethyl-cyclodecyl-methylamin-N-oxyd 生成 methylenecyclodecane
  参考文献：
  名称：

  Amine Oxides. VIII. Medium-sized Cyclic Olefins from Amine Oxides and Quaternary Ammonium Hydroxides^1,2

  摘要：

  Thermal decompositions of the N-oxides derived from N,N-dimethyl-1-methylcycloalk,lamines II having eight-, nine- and ten-membered rings yield olefin mixtures containing 98.6, 94.0 and 97.5%, respectively, of 1-methylcycloalkenes. Considerable amounts of the trans isomers are formed from the nine- and ten-membered N-oxides. Pyrolyses of the corresponding quaternary hydroxides produce mixtures of methylenecycloalkanes and 1-methylcycloalkenes (predominantly cis), violation of the Hofmann rule being at a maximum in the decomposition of the nine-membered quaternary hydroxide. Importance of relative product stabilities and the operation of non-bonded interactions are discussed as possible explanations for the observed directions of elimination. Thermal decompositions of the N-oxides and quaternary hydroxides of dimethylcycloalkvimethylamines IV containing eight-, nine- and ten-membered rings proceed as expected with formation of the corresponding methylenecycloalkanes.

  DOI：

  10.1021/ja01502a053

文献信息

• Ring closure of the 6-methylenecyclodecyl radical
  作者：Athelstan L.J. Beckwith、Vincent W. Bowry、Carl H. Schiesser

  DOI：10.1016/0040-4020(91)80014-s

  日期：1991.1

  cis- and trans- isomers of 9-methyldecahydro-naphthalene, in which the former predominates, but no methylenecyclodecane. The reaction involves the extremely rapid, stereoselective transannular cyclisation of the 6-methylene-cyclodecyl radical (2b). Generation of 2b by thermolysis of the tert-butyl perester, 12b, in the presence of 1,1,3,3-tetramethylisoindolinyl-2-oxyl (T·.) gives both cyclised (15, 16)

  用三丁基锡烷处理衍生自6-亚甲基环癸醇的二硫代碳酸酯10a，得到9-甲基十氢萘的顺式和反式异构体的混合物，其中前者占优势，但没有亚甲基环癸烷。该反应涉及6-亚甲基-环癸基自由基（2b）的极快的立体选择性环环化。在1,1,3,3-四甲基异吲哚基-2-氧（T·）存在下，叔丁基过酸酯12b的热解生成2b既可以环化（15、16），也可以不环化（14）） 产品。数据的通常处理得到ķ Ç ≈3×10 10小号-1在80℃下，其中ķ Ç是用于环化的速率常数2b中。
• Kinetics of carbenium ion additions to methylenecycloalkanes: cycloalkyl cation stabilities are not predominantly controlled by strain
  作者：Michael Roth、Christian Schade、Herbert Mayr

  DOI：10.1021/jo00080a027

  日期：1994.1

  Kinetic investigations of the reactions of the (p-anisyl)phenylcarbenium tetrachlordborate (1 BCl4- with methylenecycloalkanes (ring size 3-12 and 15) have-been performed. The second-order rate constants correlate with the solvolysis rates of the corresponding cycloalkyl derivatives, though none of the ring carbons is rehybridized in the rate-determining step (electrophilic attack of 1 at the CC double bond). A simple explanation fdr the observed rate effects cannot be given, and it is claimed that the common rationalization of cycloalkyl solvolysis rates by differences of internal strain has to be modified.
• Cycloalkylmethyl radicals. 5. 6- to 15-membered rings: ESR studies of ring conformations and stereodynamics
  作者：Keith U. Ingold、J. C. Walton

  DOI：10.1021/ja00257a006

  日期：1987.11
• Reduction of [(phenylthio)methyl]carbinyl benzoate esters to alkenes with titanium metal
  作者：Steven C. Welch、Jiann-Ping Loh

  DOI：10.1021/jo00333a030

  日期：1981.9
• Amine Oxides. VIII. Medium-sized Cyclic Olefins from Amine Oxides and Quaternary Ammonium Hydroxides^1,2
  作者：Arthur C. Cope、Engelbert Ciganek、Charles F. Howell、Edward E. Schweizer

  DOI：10.1021/ja01502a053

  日期：1960.9

  Thermal decompositions of the N-oxides derived from N,N-dimethyl-1-methylcycloalk,lamines II having eight-, nine- and ten-membered rings yield olefin mixtures containing 98.6, 94.0 and 97.5%, respectively, of 1-methylcycloalkenes. Considerable amounts of the trans isomers are formed from the nine- and ten-membered N-oxides. Pyrolyses of the corresponding quaternary hydroxides produce mixtures of methylenecycloalkanes and 1-methylcycloalkenes (predominantly cis), violation of the Hofmann rule being at a maximum in the decomposition of the nine-membered quaternary hydroxide. Importance of relative product stabilities and the operation of non-bonded interactions are discussed as possible explanations for the observed directions of elimination. Thermal decompositions of the N-oxides and quaternary hydroxides of dimethylcycloalkvimethylamines IV containing eight-, nine- and ten-membered rings proceed as expected with formation of the corresponding methylenecycloalkanes.