(+)-9-bromocamphor | 64474-56-2

• 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: (+)-9-bromocamphor
• 英文别名: (-)-9-bromocamphor；(7S)-9-Brom-bornan-2-on；(1S,4S,7S)-7-(bromomethyl)-1,7-dimethylbicyclo[2.2.1]heptan-2-one
• CAS: 64474-56-2
• 化学式: C₁₀H₁₅BrO
• 分子量: 231.132
• InChiKey: JOXACTPHKLKJNP-SFGNSQDASA-N

物化性质

• 沸点：
  269.4±13.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  (+)-9-bromocamphor 在 sodium naphthaleimide 、 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 (+)-对-薄荷-1-烯
  参考文献：
  名称：

  Synthesis and absolute configuration of the antiparasitic furanosesquiterpenes (-)-furodysin and (-)-furodysinin. Camphor as a six-membered ring chiral pool template

  摘要：

  The syntheses of (-)-furodysin ((-)-2a) and (-)-furodysinin ((-)-3a) in four steps starting from (+)-9-bromocamphor (18) has been accomplished, thus establishing the absolute configuration of these and related metabolites. This was made possible by the unexpected exo selectivity in the aldol condensation of camphor-like enolates with aldehydes. This has been found to be a general phenomenon in the camphor system. Further, anionic fragmentation of the C1-C7 bond of camphor derivatives has allowed access to synthetic intermediates containing functionalized six-membered rings, thus opening up avenues from camphor to a new class of chiral pool elements not currently available from chiral pool substances.

  DOI：

  10.1021/jo00001a069
• 作为产物：
  描述：

  (+/-)-<8,10-¹⁴C2>Campher-9-sulfonylbromid 生成 (+)-9-bromocamphor
  参考文献：
  名称：

  Racemization of camphor during .pi. sulfonation

  摘要：

  DOI：

  10.1021/ja01034a025

文献信息

• Transformations of camphor
  作者：K.M. Baker、B.R. Davis

  DOI：10.1016/s0040-4020(01)82472-8

  日期：1968.1

  and di-ethyleneketals of bornane-2,3-dione have been utilised for selective reactions in this molecule, including a new route to epicamphor. The alkylation of camphor with sodium and methyl iodide gave both C- and O-alkylation. A discepancy in the literature concerning the synthesis of homocamphor and homoepicamphor is rectified. The reaction of 9-bromobornan-2-one with zinc and acetic aicd-d1 gave

  硼烷-2，3-二酮的单和二亚乙基缩酮已被用于该分子的选择性反应，包括新的环氧树胶途径。樟脑与钠和甲基碘的烷基化得到C-和O-烷基化。文献中有关同型樟脑和同型表足的合成存在的分歧已得到纠正。9-溴硼烷-2-酮与锌和乙酸-aid-d 1的反应既得到了9-氘代化合物，又得到了片段化反应的产物。
• Guha; Bhattacharyya, Journal of the Indian Chemical Society, 1944, vol. 21, p. 280,283
  作者：Guha、Bhattacharyya

  DOI：——

  日期：——
• Asahina; Ishidate, Chemische Berichte, 1935, vol. 68, p. 947,952
  作者：Asahina、Ishidate

  DOI：——

  日期：——
• A new hydroxydiphosphine as a ligand for Rh(I)-catalyzed enantioselective hydrogenation
  作者：Igor V. Komarov、Axel Monsees、Renat Kadyrov、Christine Fischer、Ute Schmidt、Armin Börner

  DOI：10.1016/s0957-4166(02)00372-5

  日期：2002.8

  A new diphosphine ligand bearing a hydroxy group in the backbone was synthesized starting from 9-bromocamphor. The rhodium(I) complex based on this ligand was tested in the hydrogenation of alpha- and beta-amino acid precursors. The activity and selectivity of the catalyst were found to be strongly dependent upon the nature of the substrate. Thus. beta-acetylamino carboxylates were obtained with up to 97% ee. (C) 2002 Published by Elsevier Science Ltd.
• Nishimitsu; Nishikawa; Hagiwara, Proceedings of the Japan Academy, 1951, vol. 27, p. 285
  作者：Nishimitsu、Nishikawa、Hagiwara

  DOI：——

  日期：——