2-[2-(1-萘)乙基]环氧乙烷 | 111990-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-[2-(1-萘)乙基]环氧乙烷
• 英文名称: 1,2-epoxy-4-(1-naphthyl)butane
• 英文别名: Oxirane, 2-(2-(1-naphthalenyl)ethyl)-；2-(2-naphthalen-1-ylethyl)oxirane
• CAS: 111990-50-2
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: RRNNFTXINDHWIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  2-[2-(1-萘)乙基]环氧乙烷 在 碘化铵 、 lithium perchlorate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以51%的产率得到1-iodo-4-(1-naphthyl)butan-2-ol
  参考文献：
  名称：

  Exploratory Studies on Reactions of Cobaloxime π-Cations with C-Nucleophiles:  Irreversible Alkene Decomplexation versus Nucleophilic Capture

  摘要：

  (beta-Hydroxyalkyl)- and (beta-acetoxyalkyl)cobaloximes can undergo facile acid-catalyzed P-heteroatom exchange with oxygen and nitrogen nucleophiles in an S(N)1-like mechanism via cationic metal-alkene pi-complex intermediates (cobaloxime pi-cations). The reaction of cobaloxime pi-cations with carbon nucleophiles has not been previously reported. The results reported in this paper demonstrate that cobaloxime pi-cations are reasonably good electrophiles. They are sufficiently reactive to add to the electron-rich sp(2) centers in allyltrimethylsilane and pyrrole. A major side reaction for intermolecular reactions is irreversible alkene decomplexation. An intramolecular pyrrole cyclization (22 to 23, 83% yield) significantly raised the yield for nucleophilic addition compared to that of the analogous intermolecular couplings (12b tb 13b, 32% yield and 17 to 18, 29% yield). The results of these studies provide a foundation for the design and evaluation of modified cobalt ligands with the goal of suppressing alkene decomplexation and enhancing reaction of cobaloxime pi-cations with C-nucleophiles.

  DOI：

  10.1021/jo951319i
• 作为产物：
  描述：

  1-(but-3-en-1-yl)naphthalene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 以99%的产率得到2-[2-(1-萘)乙基]环氧乙烷
  参考文献：
  名称：

  Exploratory Studies on Reactions of Cobaloxime π-Cations with C-Nucleophiles:  Irreversible Alkene Decomplexation versus Nucleophilic Capture

  摘要：

  (beta-Hydroxyalkyl)- and (beta-acetoxyalkyl)cobaloximes can undergo facile acid-catalyzed P-heteroatom exchange with oxygen and nitrogen nucleophiles in an S(N)1-like mechanism via cationic metal-alkene pi-complex intermediates (cobaloxime pi-cations). The reaction of cobaloxime pi-cations with carbon nucleophiles has not been previously reported. The results reported in this paper demonstrate that cobaloxime pi-cations are reasonably good electrophiles. They are sufficiently reactive to add to the electron-rich sp(2) centers in allyltrimethylsilane and pyrrole. A major side reaction for intermolecular reactions is irreversible alkene decomplexation. An intramolecular pyrrole cyclization (22 to 23, 83% yield) significantly raised the yield for nucleophilic addition compared to that of the analogous intermolecular couplings (12b tb 13b, 32% yield and 17 to 18, 29% yield). The results of these studies provide a foundation for the design and evaluation of modified cobalt ligands with the goal of suppressing alkene decomplexation and enhancing reaction of cobaloxime pi-cations with C-nucleophiles.

  DOI：

  10.1021/jo951319i

文献信息

• Processes for production of optically active epoxides
  申请人：DAICEL CHEMICAL INDUSTRIES CO., LTD.

  公开号：EP0611826A2

  公开（公告）日：1994-08-24

  A microorganism or a preparation thereof is permitted to act on a mixture of enantiomers of an epoxide such as 3-chlorostyrene oxide and the product optically active epoxide is recovered. The microorganism able to produce an optically active (S)-epoxide from the mixture of enantiomers of the epoxide include, for example, a microorganism strain belonging to the genus Candida, the genus Rhodosporidium, the genus Rhodococcus and the genus Nosardioides. Examples of the microorganism capable of producing an optically active (R)-epoxide from said mixture include a microorganism strain belonging to the genus Trichosporon, the genus Geotrichum, the genus Corynebacterium, the genus Micrococcus and the genus Brevibacterium. The objective optically active epoxide can efficiently be obtained with ease and simplicity from the corresponding mixture of enantiomers of the epoxide.

  允许微生物或其制剂作用于环氧化物（如 3-氯苯乙烯氧化物）的对映体混合物，并回收光学活性环氧化物产品。能够从环氧化物的对映体混合物中产生光学活性（S）-环氧化物的微生物包括，例如，属于白色念珠菌属、Rhodosporidium 属、Rhodococcus 属和 Nosardioides 属的微生物菌株。能够从所述混合物中产生光学活性（R）-环氧化物的微生物菌株的例子包括属于三孢菌属、革囊菌属、高丽杆菌属、微球菌属和布雷维杆菌属的微生物菌株。从相应的环氧化物对映体混合物中可以高效、简便地获得具有光学活性的环氧化物。
• US5672504A
  申请人：——

  公开号：US5672504A

  公开（公告）日：1997-09-30
• Exploratory Studies on Reactions of Cobaloxime π-Cations with C-Nucleophiles:  Irreversible Alkene Decomplexation versus Nucleophilic Capture
  作者：Jennifer L. Gage、Bruce P. Branchaud

  DOI：10.1021/jo951319i

  日期：1996.1.1

  (beta-Hydroxyalkyl)- and (beta-acetoxyalkyl)cobaloximes can undergo facile acid-catalyzed P-heteroatom exchange with oxygen and nitrogen nucleophiles in an S(N)1-like mechanism via cationic metal-alkene pi-complex intermediates (cobaloxime pi-cations). The reaction of cobaloxime pi-cations with carbon nucleophiles has not been previously reported. The results reported in this paper demonstrate that cobaloxime pi-cations are reasonably good electrophiles. They are sufficiently reactive to add to the electron-rich sp(2) centers in allyltrimethylsilane and pyrrole. A major side reaction for intermolecular reactions is irreversible alkene decomplexation. An intramolecular pyrrole cyclization (22 to 23, 83% yield) significantly raised the yield for nucleophilic addition compared to that of the analogous intermolecular couplings (12b tb 13b, 32% yield and 17 to 18, 29% yield). The results of these studies provide a foundation for the design and evaluation of modified cobalt ligands with the goal of suppressing alkene decomplexation and enhancing reaction of cobaloxime pi-cations with C-nucleophiles.