Sodium; cyclohex-2-enolate | 87782-10-3

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: Sodium; cyclohex-2-enolate
• CAS: 87782-10-3
• 化学式: C₆H₉O*Na
• 分子量: 120.127
• InChiKey: VSZVNCBEICKYKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.54
• 重原子数：
  8.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  23.06
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  Sodium; cyclohex-2-enolate 在 bis(2,4,6-trimethylpyridine)silver(I) perchlorate 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 3-tert-butyl-4-bromo-3aα,4β,5,6,7,7aα-hexahydrobenzoxazolin-2-one
  参考文献：
  名称：

  Synthesis of protected aminocyclohexanediols

  摘要：

  DOI：

  10.1021/jo00200a009

文献信息

• Deoxygenative Dimerization of Benzylic and Allylic Alcohols, and Their Ethers and Esters Using Lanthanum Metal and Chlorotrimethylsilane in the Presence of a Catalytic Amount of Iodine and Copper(I) Iodide
  作者：Toshiki Nishino、Yutaka Nishiyama、Noboru Sonoda

  DOI：10.1246/bcsj.76.635

  日期：2003.3

  Benzylic and allylic alcohols were deoxygenatively dimerized by a treatment with lanthanum metal and chlorotrimethylsilane in the presence of a catalytic amount of iodine, giving the corresponding coupling products, alkanes, in moderate-to-good yields. This dimerization reaction was dramatically accelerated by the addition of a catalytic amount of copper(I) iodide. Similarly, ethers and esters were

  在催化量的碘存在下，通过用镧金属和三甲基氯硅烷处理使苄醇和烯丙醇脱氧二聚，得到相应的偶联产物，烷烃，产率中等至良好。通过添加催化量的碘化铜 (I)，这种二聚反应显着加速。类似地，醚和酯在催化量的 H2O 存在下通过 La/Me3SiCl/cat.I2/cat.CuI 系统脱氧二聚。
• Oxygen and nitrogen heterocycles by intramolecular magnesium- and zinc-ene reactions; Methylenecyclopentanes by Pd(0) - catalyzed isomerization of 5-(bromozincmethyl)-3-methyleneoxacycloalkanes
  作者：J. van der Louw、J.L. van der Baan、H. Stieltjes、F. Bickelhaupt、G.W. Klumpp

  DOI：10.1016/s0040-4039(01)81093-5

  日期：1987.1

  2-(Alkenyloxymethyl)-2-propenylzinc bromides 2a-e and 2-(allylmethylaminomethyl)-2-propenylzinc (or magnesium) halides 2g rearrange thermally to 5-(l-bromozincalkyl)-3-methyleneoxacycloalkanes 1a-e and 5-(bromozinc[or chloromagnesium]methyl)-3-methylene-N-methylpiperidine 1g; some of the former can be isomerized by Pd(PPh3)4 to methylenecyclopentanes 3.

  2-（烯氧基氧甲基）-2-丙烯基溴化锌2a - e和2-（烯丙基甲基氨基甲基）-2-丙烯基锌（或镁）卤化物2g热重排成5-（1-溴锌烷基）-3-亚甲基氧杂环烷烃1a - e和5-（溴锌[或氯镁]甲基）-3-亚甲基-N-甲基哌啶1g ; 某些前者可以被Pd（PPh 3）4异构化为亚甲基环戊烷3。
• Cyclizations and Rearrangements of Samarium Diiodide-Generated Vinyl Radicals
  作者：Laura Capella、Pier Carlo Montevecchi、Maria Luisa Navacchia

  DOI：10.1021/jo00128a013

  日期：1995.11

  Vinyl bromides 1, 5, 15, 20, 23, 27, 33a,b, 41a-c, 44a-c, 46a,b, 52a,b, 55a, 56a,b, and 60a,b react with samarium diiodide in THF and/or acetonitrile to give the corresponding vinyl radicals. Radicals 3, 7, and 16 afforded products deriving from cyclization on the adjacent triple bond in a 5-(pi-exo)exo, 6-(pi-endo)exo, and 6-(pi-exo)exo mode, respectively. Radical 7 undergoes competitive 1,5-hydrogen translocation. Vinyl radicals 21 and 24 readily cyclize on the proximal double bond, leading to 5- and 6-membered rings, respectively. Thienyl-substituted radical 28 leads to a product deriving from 5-exo cyclization on the thiophene ring and subsequent beta-fission of the C-S bond, whereas thienyl-substituted radicals 34a,b undergo almost exclusively 1,5-hydrogen translocation. Aryl-substituted radicals obtained from vinyl bromides 41, 44, 46, 52, and 55 do not form any products deriving from 5-exo or 6-exo cyclization (or ipso cyclization). Finally, naphthyl-substituted radicals 57a and 61a give only direct reduction products, whereas the radical 61b affords, in addition to the direct reduction product, a rearranged product deriving from a 1,3-radical migration of the naphthylthio group. Evidence is reported for the reduction of EWG-substituted benzene rings and thio-substituted naphthalene rings to radical anions, which can fragment on the side chain with the elimination of allyl radicals. alpha-Oxy(and alpha-thio)-substituted radicals deriving from 1,5-shift rearrange to alcohols (and thiols) through a Wittig rearrangement or a cyclization/fragmentation process.
• Rearrangement/Bromocyclization of O-Cyclohexenyl Carbamidates. Model Studies for Aminocyclitol Synthesis
  作者：Spencer Knapp、Dinesh V. Patel

  DOI：10.1016/s0040-4039(00)87663-7

  日期：1982.1