1,5-二氮杂萘-2-羧酸,5,6,7,8-四氢-3-甲基-,乙基酯 | 824-58-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 1,5-二氮杂萘-2-羧酸,5,6,7,8-四氢-3-甲基-,乙基酯
• 中文别名: 1-[(1R)-双环[2.2.1]庚-2-基]乙酮
• 英文名称: (+/-)-2-exo-Norbornyl methyl ketone
• 英文别名: exo-2-Norbornylmethylketon；2-exo-acetylnorbornane；exo-2-acetylnorbornane；2-acetylnorbornene；(+/-)-1-(norbornyl-(2exo))-ethanone-(1)；(+/-)-1-(Norbornyl-(2exo))-aethanon-(1)；Ethanone, 1-bicyclo[2.2.1]hept-2-yl-, (1R-exo)-(9CI)；1-[(1R,2R,4S)-2-bicyclo[2.2.1]heptanyl]ethanone
• CAS: 824-58-8；824-59-9；58654-66-3；109583-34-8；115184-20-8；130404-11-4；130405-13-9；130405-16-2；130405-17-3
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: NDZIFIKZHLSCFR-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,5-二氮杂萘-2-羧酸,5,6,7,8-四氢-3-甲基-,乙基酯 在 盐酸羟胺 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以60%的产率得到exo-2-Norbornylmethylketonoxim
  参考文献：
  名称：

  Langhals, Heinz; Range, Guenter; Wistuba, Eckehardt, Chemische Berichte, 1981, vol. 114, # 12, p. 3813 - 3830

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 potassium acetate 作用下， 以 苯 为溶剂， 反应 3.0h， 以95%的产率得到1,5-二氮杂萘-2-羧酸,5,6,7,8-四氢-3-甲基-,乙基酯
  参考文献：
  名称：

  Palladium-catalyzed norbornene-carbon monoxide co-oligomerization initiated by aryl groups and terminated by double bond formation

  摘要：

  The use of m-iodophenol as initiator in palladium-catalyzed norbornene-carbon monoxide oligomerization in the presence of potassium acetate unexpectedly leads to termination by double bond formation in spite of the limitations to beta-H-anti elimination. The presence of endo products points to preliminary exo-to-endo isomerization through enolization. The X-ray structure of one stereoisomer (Ia) is given.

  DOI：

  10.1016/0022-328x(92)85082-8

文献信息

• [EN] PROCESS FOR THE SYNTHESIS OF BETA-AMINOCARBONYLS<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE BÉTA-AMINOCARBONYLES
  申请人：UNIV OTTAWA

  公开号：WO2013067646A1

  公开（公告）日：2013-05-16

  The present application provides processes and intermediates useful in the production of β- aminocarbonyl- or β-aminothiocarbonyl-containing compounds. Provided herein is a process for synthesizing β-aminocarbonyl- or β-aminothiocarbonyl-containing compounds from an alkene and a hydrazone. Also provided herein is a process for synthesizing β-aminocarbonyl- or β-aminothiocarbonyl-containing compounds from an alkene and a hydrazine. The present application further provides intermediate aminoisocyanate and iminoisocyanate compounds, and methods for synthesizing the starting hydrazone and hydrazine compounds.

  本申请提供了在生产β-氨基羰基或β-氨基硫代羰基含有化合物中有用的过程和中间体。本文提供了一种从烯烃和肼酮合成β-氨基羰基或β-氨基硫代羰基含有化合物的方法。本文还提供了一种从烯烃和肼合成β-氨基羰基或β-氨基硫代羰基含有化合物的方法。本申请进一步提供了中间体氨基异氰酸酯和亚氨基异氰酸酯化合物，以及合成起始肼酮和肼化合物的方法。
• Solvent-Free Chelation-Assisted Catalytic CC Bond Cleavage of Unstrained Ketone by Rhodium(I) Complexes under Microwave Irradiation
  作者：Jeong-Ae Ahn、Duck-Ho Chang、Young Jun Park、Ye Rim Yon、André Loupy、Chul-Ho Jun

  DOI：10.1002/adsc.200505233

  日期：2006.1

  A highly efficient CC bond cleavage of unstrained aliphatic ketones bearing β-hydrogens with olefins was achieved using a chelation-assisted catalytic system consisting of (Ph3P)3RhCl and 2-amino-3-picoline by microwave irradiation under solvent-free conditions. The addition of cyclohexylamine catalyst accelerated the reaction rate dramatically under microwave irradiation compared with the classical

  使用由（Ph 3 P）3 RhCl和2-氨基-3-甲基吡啶组成的螯合辅助催化体系，在无溶剂条件下通过微波辐照，实现了高效的CC键裂解含β氢的未应变脂族酮与烯烃的CC键裂解。。与传统的加热方法相比，在微波辐射下添加环己胺催化剂可显着加快反应速度。
• Double Acylation of Alkenes with Acylchromates Promoted by Cationic Pd(II) Complex
  作者：Motoki Yamane、Yuichiro Ishibashi、Hidehiro Sakurai、Koichi Narasaka

  DOI：10.1246/cl.2000.174

  日期：2000.2

  Double acylation of alkenes such as norbornene and vinylsilane proceeds by the use of acylchromate complexes and a cationic Pd(II) complex. When two different acylchromates are added successively to a mixture of alkene and the Pd complex, unsymmetrical diketones are obtained almost selectively.

  通过使用酰基铬酸盐络合物和阳离子钯（II）络合物，可以对烯烃（如降冰片烯和乙烯基硅烷）进行双酰化。将两种不同的酰基铬酸盐先后加入烯和钯络合物的混合物中，几乎可以选择性地得到不对称的二酮。
• Kuchin, A. V.; Nurushev, R. A.; Khalilov, L. M., Journal of general chemistry of the USSR, 1987, p. 1574 - 1579
  作者：Kuchin, A. V.、Nurushev, R. A.、Khalilov, L. M.、Tolstikov, G. A.

  DOI：——

  日期：——
• Hydroboration. 87. Controlled and sequential hydroboration of simple representative alkenes with methylborane in tetrahydrofuran. An examination of the directive effects in the first and second stages of hydroboration
  作者：Morris Srebnik、Thomas E. Cole、Herbert C. Brown

  DOI：10.1021/jo00304a017

  日期：1990.8