cis-(3S,4R)-3,4-epoxynonane | 935701-22-7

• 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: cis-(3S,4R)-3,4-epoxynonane
• 英文别名: (3S,4R)-3,4-epoxynonane；(2S,3R)-2-ethyl-3-pentyloxirane
• CAS: 935701-22-7
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: BRBFKTQUGYOOEX-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  1.0
• 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

反应信息

• 作为反应物：
  描述：

  cis-(3S,4R)-3,4-epoxynonane 在 ((1S,2R,5S)-2-i-Pr-5-Me-cyclohex-1-yl)Cp)2TiCl₂ 1,4-环己二烯 、 2,4,6-collidine hydrochloride 、 锌 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-壬烷-3-醇
  参考文献：
  名称：

  Titanocene-Catalyzed Regiodivergent Epoxide Openings

  摘要：

  The first regiodivergent opening of unbiased epoxides providing the ring-opened products in high enantiomeric excess from racemic and exceptionally high enantiomeric excess from enantioenriched substrates in a double asymmetric process has been devised. It constitutes a more general case of the very important enantioselective openings of meso-epoxides.

  DOI：

  10.1021/ja0686211
• 作为产物：
  描述：

  (2Z)-2-辛烯-1-醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 copper(l) iodide 、 L-(+)-酒石酸二乙酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 cis-(3S,4R)-3,4-epoxynonane
  参考文献：
  名称：

  Titanocene-Catalyzed Regiodivergent Epoxide Openings

  摘要：

  The first regiodivergent opening of unbiased epoxides providing the ring-opened products in high enantiomeric excess from racemic and exceptionally high enantiomeric excess from enantioenriched substrates in a double asymmetric process has been devised. It constitutes a more general case of the very important enantioselective openings of meso-epoxides.

  DOI：

  10.1021/ja0686211

文献信息

• Asymmetric total synthesis of (+)-<i>exo</i>-brevicomin based on enantioconvergent biocatalytic hydrolysis of an alkene-functionalized 2,3-disubstituted epoxide
  作者：Sandra F Mayer、Harald Mang、Andreas Steinreiber、Robert Saf、Kurt Faber

  DOI：10.1139/v02-037

  日期：2002.4.1

  A short total asymmetric synthesis of (+)-exo- and (–)-endo-brevicomin ((+)-exo-3 and (–)-endo-3), which are components of the attracting pheromone system of several bark-beetle species belonging to the genera Dendroctonus and Dryocoetes, was accomplished via a chemoenzymatic protocol. The key step consisted of biocatalytic hydrolysis by bacterial epoxide hydrolases of cis-configured 2,3-disubstituted oxiranes bearing olefinic side chains. This reaction proceeded in an enantioconvergent fashion, by affording a single enantiomeric vic-diol from the rac-epoxide in up to 92% ee and 83% isolated yield.Key words: bacterial epoxide hydrolase, 2,3-disubstituted oxirane, enantioconvergent hydrolysis, (+)-exo-brevicomin, (–)-endo-brevicomin.

  一种对多种属于Dendroctonus和Dryocoetes属树皮甲虫物种的吸引信息素系统中的成分（+）-exo-和（-）-endo-brevicomin进行的短程不对称合成，通过化学酶联合协议完成。关键步骤包括细菌环氧化酶的生物催化水解，水解的是带有烯烃侧链的顺式配置2,3-二取代环氧烷。该反应以对映选择性收率高达92%的方式进行，从拉氏环氧化物中得到单对映体的双醇，隔离收率为83%。关键词：细菌环氧化酶，2,3-二取代环氧烷，对映选择性水解，（+）-exo-brevicomin，（-）-endo-brevicomin。
• Titanocene-Catalyzed Regiodivergent Epoxide Openings
  作者：Andreas Gansäuer、Chun-An Fan、Florian Keller、Jutta Keil

  DOI：10.1021/ja0686211

  日期：2007.3.1

  The first regiodivergent opening of unbiased epoxides providing the ring-opened products in high enantiomeric excess from racemic and exceptionally high enantiomeric excess from enantioenriched substrates in a double asymmetric process has been devised. It constitutes a more general case of the very important enantioselective openings of meso-epoxides.