(1S)-1-Methylbicyclo<2.2.1>heptan-2-one | 121351-01-7

• 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
• 英文名称: (1S)-1-Methylbicyclo<2.2.1>heptan-2-one
• 英文别名: l-fenchone；(S)-1-methylnorcamphor；norcamphor；(1S,4R)-1-Methyl-bicyclo<2.2.1>heptan-2-on；(1S,4R)-1-methylbicyclo[2.2.1]heptan-2-one
• CAS: 121351-01-7
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: ZYVCBPCUGIGFJA-XPUUQOCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (1S)-1-Methylbicyclo<2.2.1>heptan-2-one 在 二乙醇胺 、 (-)-diisopinocamphenylborane chloride 作用下， 生成 (1S)-1-Methylbicyclo<2.2.1>heptan-exo-2-ol
  参考文献：
  名称：

  Chiral Synthesis via Organoboranes. 43. Selective Reductions. 58. Reagent-Controlled Diastereoselective Reduction of (+)- and (−)-α-Chiral Ketones with (+)- and (−)-B-Chlorodiisopinocampheylborane

  摘要：

  Asymmetric reduction of (+)- and (-)-alpha-chiral ketones with (+)- and (-)-B-chlorodiisopinocampheylborane provides the product alcohols in very high diastereomeric excess, with the matched pairs providing >100:1 selectivity and the mismatched pairs showing 4:1-15:1 selectivity. The high selectivity achieved even in the mismatched pairs reveals the power of the reagent to control the stereochemical outcome. The rates of the reaction of the matched pairs are faster than those of the mismatched pairs, In all the cases studied thus far, the (-)-reagent ((d)Ipc(2)BCl) and (S)ketone or the (+)-reagent ((l)Ipc(2)BCl) and (R)-ketone constitute matched pairs and the (-)-reagent and (R)-ketone or the (+)-reagent and (S)-ketone constitute mismatched pairs, A possible mechanism for the reductions is discussed.

  DOI：

  10.1021/jo951207r
• 作为产物：
  描述：

  (1S,2R)-1-methyl-2-norbornanol 在 calcium hypochlorite 作用下， 以 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 1.0h， 以92%的产率得到(1S)-1-Methylbicyclo<2.2.1>heptan-2-one
  参考文献：
  名称：

  用次氯酸钙[Ca（OCl）2 ]氧化醇和醚

  摘要：

  次氯酸钙是一种相对稳定，易于储存和使用的固体次氯酸盐氧化剂，被发现可以以优异的产率将仲醇氧化为酮。伯醇产生酯，其中酯的酸和醇部分均来自醇。尽管仅以中等收率，但醚被氧化成酯。

  DOI：

  10.1016/s0040-4039(00)97525-7

文献信息

• Chiral Synthesis via Organoboranes. 42. Selective Reductions. 57. Efficient Kinetic Resolution of Representative α-Tertiary Ketones with <i>B</i>-Chlorodiisopinocampheylborane
  作者：P. Veeraraghavan Ramachandran、Guang-Ming Chen、Herbert C. Brown

  DOI：10.1021/jo951206z

  日期：1996.1.1

  Kinetic resolution of racemic alpha-tertiary ketones with 0.5-0.6 molar equiv of B-chlorodiisopinocampheylborane provides the product alcohols in very high diastereomeric and enantiomeric excess, with the unreacted ketone recovered in very high ee. For example, ethyl 1-methyl-8-oxocyclopentane- and -cyclohexanecarboxylates are partially reduced to recover the ketone in 91 greater than or equal to 99% ee and the product alcohols in up to 94% de, with >90% ee for the major diastereomer. Bicyclic ketones, such as 1-methyl- and 1-ethylnorcamphor, camphor, and camphenilone, are readily resolved to provide the ketone in 92 to greater than or equal to 99% ee, with the product alcohol recovered in high de and ee. Dihydrospiro[bicyclo[3.2.1]octane-2,2'(3'H)-furan]-3-one is resolved to provide the ketone in greater than or equal to 99% ee and the product alcohol in greater than or equal to 99% de. In all the cases studied, the R-isomer of the ketone is recovered when (d)Ipc(2)BCl is used for kinetic resolution, while (l)Ipc(2)BCl provides the S-ketone. Optimum conditions for obtaining the product alcohol, or the ketone, or both, in very high yields and ee have been established.
• Herrmann, Roland; Kirmse, Wolfgang, Liebigs Annalen, 1996, # 4, p. 435 - 438
  作者：Herrmann, Roland、Kirmse, Wolfgang

  DOI：——

  日期：——
• CHA, JIN SOON;YOON, MAL SOOK;KIM, YOUNG SHICK;LEE, KWANG WOO, TETRAHEDRON LETT., 29,(1988) N 9, 1069-1070
  作者：CHA, JIN SOON、YOON, MAL SOOK、KIM, YOUNG SHICK、LEE, KWANG WOO

  DOI：——

  日期：——
• [EN] 5,6,7,8-TETRAHYDRO-5,8-METHANOCINNOLINE DERIVATIVES AS RORC MODULATORS FOR THE TREATMENT OF AUTOIMMUNE DISEASES<br/>[FR] DÉRIVÉS DE 5,6,7,8-TÉTRAHYDRO-5,8-MÉTHANOCINNOLINE À TITRE DE MODULATEURS RORC POUR LE TRAITEMENT DES MALADIES AUTO-IMMUNES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015067575A1

  公开（公告）日：2015-05-14

  Compounds of the formula (I) : or a pharmaceutical salt thereof, wherein X, Ar1, R, R2, R3, R4, R5, R6 and R7 are as defined herein.. Also disclosed are methods of making the compounds and using the compounds for treatment of inflammatory diseases such as arthritis.
• The oxidation of alcohols and ethers using calcium hypochlorite [Ca(OCl)2]
  作者：Stephen O. Nwaukwa、Philip M. Keehn

  DOI：10.1016/s0040-4039(00)97525-7

  日期：1982.1

  Calcium hypochlorite, a relatively stable, and easily stored and used solid hypochlorite oxidant, was found to oxidize secondary alcohols to ketones in excellent yields. Primary alcohols gave esters where both the acid and the alcohol portions of the esters were derived from the alcohol. Ethers were oxidized to esters though only in moderate yield.

  次氯酸钙是一种相对稳定，易于储存和使用的固体次氯酸盐氧化剂，被发现可以以优异的产率将仲醇氧化为酮。伯醇产生酯，其中酯的酸和醇部分均来自醇。尽管仅以中等收率，但醚被氧化成酯。