trans-epoxycyclododecane | 286-99-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: trans-epoxycyclododecane
• 英文别名: trans-Epoxy-cyclododecan；trans-Epoxycyclododecan；(1S,12S)-13-oxabicyclo[10.1.0]tridecane
• CAS: 286-99-7；1502-29-0；4683-60-7
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: VLJLXEKIAALSJE-RYUDHWBXSA-N

物化性质

• 沸点：
  130-133 °C(Press: 15 Torr)
• 密度：
  0.9603 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R38
• WGK Germany：
  2
• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  trans-epoxycyclododecane 在 aluminum oxide 、 氢氧化钾 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 cis-1,2-cyclododecanediol
  参考文献：
  名称：

  Organic reactions at alumina surfaces. Mild and selective opening of epoxides by alcohols, thiols, benzeneselenol, amines, and acetic acid

  摘要：

  DOI：

  10.1021/ja00467a014
• 作为产物：
  描述：

  环氧十二烷 在 dilithium tetrachlorocuprate 、 甲基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 150.0h， 以55%的产率得到trans-epoxycyclododecane
  参考文献：
  名称：

  Odor–Structure Relationships Using Fluorine as a Probe

  摘要：

  Eight ethers, nine esters and one ketone were submitted to a systematic structural variation by replacing a hydrogen atom in the vicinity of the oxofunction by fluorine and methyl. As long as steric factors dominate, a fluorine substituent alters the olfactory properties of the parent compound much less than a methyl substituent does. However, if it occupies a position adjacent to a carbonyl group the halogen may more profoundly affect the odor perception, presumably as a consequence of conformational changes. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00351-3

文献信息

• Ring Opening of Oxiranes by Trimethylsilyl Trifluoromethanesulfonate
  作者：Sizuaki Murata、Masaaki Suzuki、Ryoji Noyori

  DOI：10.1246/bcsj.55.247

  日期：1982.1

  Trimethylsilyl trifluoromethanesulfonate promotes ring opening reactions of oxirane derivatives. The reaction course is highly affected by the structures and substitution pattern of the substrates. Tetra-, tri-, and 2,2-disubstituted oxiranes and simple cycloalkene oxides are converted to the corresponding allylic alcohol trimethylsilyl ethers. The overall transformation is interpreted in terms of

  Trimethylsilyl trifluoromethanesulfonate 促进环氧乙烷衍生物的开环反应。反应过程受底物结构和取代模式的影响很大。四-、三-和2,2-二取代的环氧乙烷和简单的环烯氧化物被转化为相应的烯丙醇三甲基甲硅烷基醚。总体转化解释为三氟甲磺酸甲硅烷基酯反式加成到环氧乙烷环上，然后是碱促进的三氟甲磺酸元素的反消除。2,3-二烷基-或单烷基环氧乙烷分别异构化为相应的酮和醛。(Z)-氧化环辛烯经历跨环反应生成内-顺-2-三甲基甲硅烷氧基双环[3.3.0]辛烷。6-methyl-5-hepten-2-one 氧化物反应生成 2,2, 6-trimethyl-3-trimethylsiloxy-3,4-dihydro-2H-pyran。1,2-甲基迁移发生在 (E)-3α-t-丁基二甲基甲硅烷氧基-5α-孕烯 17α,20-氧化物反应中，得到 3α-t-丁基二甲基...
• Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions – synthesis of halohydrins and epoxides
  作者：Akihiro Shimizu、Ryutaro Hayashi、Yosuke Ashikari、Toshiki Nokami、Jun-ichi Yoshida

  DOI：10.3762/bjoc.11.27

  日期：——

  β-Haloalkoxysulfonium ions generated by the reaction of electrogenerated Br⁺ and I⁺ ions stabilized by dimethyl sulfoxide (DMSO) reacted with sodium hydroxide and sodium methoxide to give the corresponding halohydrins and epoxides, respectively, whereas the treatment with triethylamine gave α-halocarbonyl compounds.

  β-卤代烷氧基磺鎓离子由电化学生成的Br⁺和I⁺离子与二甲基亚砜（DMSO）稳定后，与氢氧化钠和甲氧基钠反应，分别生成相应的卤水合物和环氧化物，而与三乙胺处理则生成α-卤代羰基化合物。
• REDUCTION OF ORGANIC COMPOUNDS WITH LOW-VALENT NIOBIUM (NbCl₅/NaAlH₄)
  作者：Mitsuyoshi Sato、Koichiro Oshima

  DOI：10.1246/cl.1982.157

  日期：1982.2.5

  Carbonyl compounds have been deoxygenatively dimerized to alkenes with the title reagent. Deoxygenation of epoxides to alkenes, reductive coupling of allylic and benzylic alcohols to hydrocarbons, and reduction of alkynes to alkenes are also described.

  羰基化合物已用标题试剂脱氧二聚成烯烃。还描述了环氧化物脱氧成烯烃、烯丙醇和苯甲醇还原偶联成烃以及炔烃还原成烯烃。
• Trimethysilyl triflate in organic synthesis11Part 11 of this series. Part 10: S. Murata and R. Noyori, Tetrahedron Letters 2107 (1981).
  作者：R. Noyori、S. Murata、M. Suzuki

  DOI：10.1016/s0040-4020(01)93263-6

  日期：——

  Trimethylsilyl triflate is a powerful silylating agent for organic compounds and acts as a catalyst which accelerates a variety of nucleophilic reactions in aprotic media. The reactions proceed via one-center, electrophilic coordination of the silyl group to hetero functional groups and exhibit unique selectivities.

  三氟甲磺酸三甲基甲硅烷基酯是有机化合物的强大甲硅烷基化剂，并充当催化剂，可加速非质子介质中的各种亲核反应。反应通过甲硅烷基与杂官能团的单中心亲电配位进行，并表现出独特的选择性。
• The Reductive Conversion of Some Cyclic and Acyclicvic-Epoxides to Alcohols by Means of Lithium Aluminium Hydride/Aluminium Trichloride
  作者：Vladimir Andrejevi?、Mira Bjelakovi?、Milan M. Mihailovi?、Mihailo Lj. Mihailovi?

  DOI：10.1002/hlca.19850680727

  日期：1985.11.13

  Unsubstituted medium-ring 1,2-epoxycycloalkanes and certain vic-epoxyalkanes are reduced to the corresponding alcohols very slowly when LiAlH4 alone is used as reducing agent. However, the combination of LiAlH4 and AlCl3, in a 2:1 molar ratio (with respect to 1 mol-equiv. of epoxide) used in refluxing Et2O, greatly enhances these reductions, rendering them of interest for practical purposes.

  未取代的介质环-1,2- epoxycycloalkanes和某些VIC -epoxyalkanes被时的LiAlH非常缓慢地还原成相应的醇4单独用作还原剂。但是，用于回流Et 2 O的摩尔比为2：1的LiAlH 4和AlCl 3的组合（相对于1摩尔当量的环氧化物）极大地提高了这些还原率，使它们成为实用目的。