(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl acetate | 37715-31-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl acetate
• 英文别名: 6,7-epoxygeranyl acetate；(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-yl acetate；5-(3,3-Dimethyloxiranyl)-3-methylpent-2-en-1-yl acetate；[(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl] acetate
• CAS: 37715-31-4
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: ICJOOVLSDYCSCJ-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2915390090

反应信息

• 作为反应物：
  描述：

  (E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl acetate 在 咪唑 、 sodium tetrahydroborate 、 四丁基氟化铵 、 potassium carbonate 、 过碘酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.5h， 生成 (E)-4-methyl-7-phenyl-heptan-4-ene-1-ol mesylate
  参考文献：
  名称：

  Catalytic Diastereoselective Polycyclization of Homo(polyprenyl)arene Analogues Bearing Terminal Siloxyvinyl Groups

  摘要：

  Highly diastereoselective polycyclization of homo(polyprenyl) arene analogues bearing terminal siloxyvinyl groups was catalyzed by tin(IV) chloride (10 mol %). The cyclizations of tert-butyldiphenylsilyl and triisopropylsilyl polyenol ethers gave 4 alpha(equatorial)- and 4 beta(axial)-siloxypolycycles as major isomers, respectively. The strong nucleophilicity of pro-C(9), a (6E) geometry, and a bulky silyl group effectively favored the 4 alpha-preference, whereas the weak nucleophilicity of pro-C(9), a (6Z)-geometry, and less steric hindrance of a silyl group favored the 4 beta-preference.

  DOI：

  10.1021/ol062378t
• 作为产物：
  描述：

  (E)-6-bromo-7-hydroxy-3,7-dimethyloct-2-en-1-yl acetate 在 甲醇 、 potassium carbonate 作用下， 反应 0.33h， 生成 (E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl acetate
  参考文献：
  名称：

  Selective Monocyclization of Epoxy Terpenoids Promoted by Zeolite NaY. A Short Biomimetic Synthesis of Elegansidiol and Farnesiferols B−D

  摘要：

  Epoxy terpenes cyclize readily, by confinement within zeolite NaY, to form exomethylenic cyclohexanols as the major products. The selective monocyclization of 10,11-epoxyfarnesyl acetate within NaY provides a short and efficient biomimetic route to (+/-)-elengasidiol and (+/-)-farnesiferols B-D.

  DOI：

  10.1021/ol062798i

文献信息

• Cobalt(II) Schiff's base complex catalysed oxidation of alcohols with dioxygen in the presence of ethyl 2-oxocyclopentanecarboxylate
  作者：T. Punniyamurthy、Javed Iqbal

  DOI：10.1016/s0040-4039(00)76726-8

  日期：1994.6

  Cobalt(II) Schiff's base complex 1 catalyses the oxidation of primary and secondary alcohols to aldehydes and ketones respectively, in the presence of dioxygen and ethyl 2-oxocyclopentanecarboxylate 2 at 60–70° C.

  钴（II）席夫碱络合物1起催化作用伯醇和仲醇，以醛和酮的分别的氧化，在分子氧和2-氧代环戊烷羧酸的存在下2在60-70℃下
• Rapid and Enantioselective Synthetic Approaches to Germanicol and Other Pentacyclic Triterpenes
  作者：Karavadhi Surendra、E. J. Corey

  DOI：10.1021/ja802730a

  日期：2008.7.1

  routes to the key intermediate 2 for the synthesis of the pentacyclic triterpene germanicol 1 have been developed. In the first, the ( S)-epoxide of farnesyl bromide is transformed in just three steps to the tetracyclic intermediate 7, which is converted to chiral 2 by treatment with polyphosphoric acid. The second synthetic route to 2 involves the coupling of the ( S)-epoxide 8 with vinyl iodide 9 to give

  已经开发了用于合成五环三萜锗烷醇 1 的关键中间体 2 的两条极短的合成路线。首先，法呢基溴的 (S)-环氧化物只需三个步骤即可转化为四环中间体 7，然后通过多磷酸处理将其转化为手性 2。2 的第二条合成路线涉及将 (S)-环氧化物 8 与乙烯基碘 9 偶联得到 10 和 10 的两阶段酸催化环化以形成 2。在这项工作的过程中，我们还发现了一个非常不寻常的分子内 1,5-质子从碳正离子转移到 CC 双键。(2)H-标记实验证实了该过程的细节。
• ISOPRENE OLIGOMER, POLYISOPRENE, PROCESSES FOR PRODUCING THESE MATERIALS, RUBBER COMPOSITION, AND PNEUMATIC TIRE
  申请人：Miyagi Yukino

  公开号：US20140171675A1

  公开（公告）日：2014-06-19

  The invention relates to an isoprene oligomer that contains a trans structural moiety and a cis structural moiety, which can be represented by the following formula (1), wherein at least 1 atom or group in the trans structural moiety is replaced by another atom or group. The invention also relates to a polyisoprene, which is biosynthesized using the isoprene oligomer and isopentenyl diphosphate. Further, this invention provides a rubber composition comprising the isoprene oligomer and/or the polyisoprene, and a pneumatic tire, including tire components (e.g., treads and sidewalls) formed from the rubber composition. wherein n represents an integer from 1 to 10; m represents an integer from 1 to 30; and Y represents a hydroxy group, a formyl group, a carboxy group, an ester group, a carbonyl group, or a group represented by the following formula (2):

  该发明涉及一种含有反式结构基团和顺式结构基团的异戊二烯寡聚物，可以用以下公式（1）表示，其中反式结构基团中至少有1个原子或基团被另一个原子或基团取代。该发明还涉及一种聚异戊二烯，它是使用异戊二烯寡聚物和异戊二烯二磷酸盐生物合成的。此外，该发明提供了一种橡胶组合物，包括异戊二烯寡聚物和/或聚异戊二烯，以及一种充气轮胎，其中轮胎组件（例如胎面和侧壁）由该橡胶组合物形成。 其中n表示1到10之间的整数；m表示1到30之间的整数；Y表示一个羟基、一个甲酰基、一个羧基、一个酯基、一个酰基或由以下公式（2）表示的基团。
• AlNiCl2.6H2OTHF: A new, mild and neutral system for selective reduction of organic functional groups
  作者：Bhabani K. Sarmah、Nabin C. Barua

  DOI：10.1016/s0040-4020(01)82402-9

  日期：1991.9

  A mild and neutral reducing system consisting of AlNiCl2.6H2OTHF has been developed and reacted with a series of organic compounds containing different functional groups in order to evaluate its synthetic utility. It was observed that this system very efficiently reduces the α-enones to the saturated ketones, aromatic aldehydes and ketones to the corresponding alcohols, nitriles and nitroarenes to

  由AlNiCl的温和的和中性降低系统2 ·6H 2 OTHF已经开发并用一系列含有，以评价它的合成的效用不同官能团的有机化合物的反应。观察到该体系非常有效地将α-烯酮还原为饱和酮，芳族醛和酮为相应的醇，腈和硝基芳烃为胺，酸酐和酰氯为醛，二硫化物为硫醇和环氧化物为相应的醇。 。另一方面，发现孤立的双键，羧酸，酯，内酯，伯，苄基和烯丙基卤化物，脂族醛和酮以及脂族硝基化合物对该体系保持惰性。此外，AlNiCl的还原性能2 ·6H 2 ö中也进行了研究几个其他的有机溶剂。
• Manganese(II)/Picolinic Acid Catalyst System for Epoxidation of Olefins
  作者：Ross A. Moretti、J. Du Bois、T. Daniel P. Stack

  DOI：10.1021/acs.orglett.6b00518

  日期：2016.6.3

  An in situ generated catalyst system based on Mn(CF3SO3)2, picolinic acid, and peracetic acid converts an extensive scope of olefins to their epoxides at 0 °C in <5 min, with remarkable oxidant efficiency and no evidence of radical behavior. Competition experiments indicate an electrophilic active oxidant, proposed to be a high-valent Mn = O species. Ligand exploration suggests a general ligand sphere

  基于Mn（CF 3 SO 3）2，吡啶甲酸和过氧乙酸的原位生成的催化剂体系在0°C下于<5分钟内将大量烯烃转化为环氧化物，具有显着的氧化效率并且没有自由基的迹象行为。竞争实验表明，一种亲电子活性氧化剂被认为是高价Mn = O物种。配体探索表明，一般的配体球基序有助于有效氧化。该方法以其简单性和使用廉价试剂来快速获得高附加值产品而得到强调。