(1R,1'R)-exo,exo'-3,3'-biisoborneol | 172426-81-2

• 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: (1R,1'R)-exo,exo'-3,3'-biisoborneol
• 英文别名: (1R,1'R)-3-exo,3'-exo-Biisoborneol；exo,exo'-3,3'-biisoborneol；3-exo,3'-exo-biisoborneol；(1R,2R,3S,4R)-3-[(1R,2S,3R,4R)-3-hydroxy-4,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 172426-81-2
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: ATLQLNSALJPKPX-KWPUJSDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,1'R)-exo,exo'-3,3'-biisoborneol 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 (1R,2S,3S,4R,7R,8R,11R,12R,15R,16R)-11,12-bis(1,3-benzodioxole-5-carbonyl)-7,16,19,19,20,20-hexamethyl-9,14-dioxapentacyclo[14.2.1.14,7.02,15.03,8]icosane-10,13-dione
  参考文献：
  名称：

  Stereoselective intramolecular coupling of diaroylacetates of (1R,1′R)-exo,exo′-3,3′-biisoborneol by oxidation with Br2

  摘要：

  The oxidative coupling of diaroylacetate derivatives prepared from (1R, 1'R)-exo,exo'-3,3'-biisoborneol with NaH-Br-2 gave the corresponding intramolecularly coupled products stereoselectively. The major (R,R)-isomers thus obtained were transformed to (-)-Sesamin and (-)-Eudesmin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00572-x
• 作为产物：
  描述：

  [(1R,2R,3S,4R)-3-[(1R,2S,3R,4R)-3-acetyloxy-4,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] acetate 在 lithium aluminium tetrahydride 、 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (1R,1'R)-exo,exo'-3,3'-biisoborneol
  参考文献：
  名称：

  Stereoselective intramolecular coupling of diaroylacetates of (1R,1′R)-exo,exo′-3,3′-biisoborneol by oxidation with Br2

  摘要：

  The oxidative coupling of diaroylacetate derivatives prepared from (1R, 1'R)-exo,exo'-3,3'-biisoborneol with NaH-Br-2 gave the corresponding intramolecularly coupled products stereoselectively. The major (R,R)-isomers thus obtained were transformed to (-)-Sesamin and (-)-Eudesmin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00572-x

文献信息

• 3-exo,3′-exo-(1R,1′R)-Bithiocamphor — a versatile source for functionally different 3,3′-bibornane derivatives, II. 1 An access to 3-exo,3′-exo-(1r,1′r)-bicamphor and related compounds
  作者：Werner Schroth、Ekkehard Hintzsche、Roland Spitzner、Dieter Ströhl、Katrin Schmeiβ、Joachim Sieler

  DOI：10.1016/0040-4020(95)00849-4

  日期：1995.11

  3-exo,3′-exo-(1R,1′R)-bicamphor (12) is obtained from 3-exo,3′-exo-(1R,1′R)-bithtiocamphor (3) by condensation with hydrazine hydrate followed by hydrolysis of the resulting dihydropyridazine 11. Deprotonation of 12 with NaH and subsequent treatment with potassium hexacyanoferrate (III) furnishes the 2,2′-dioxo-3,3′-bibornanylidene 13, whilst reduction of 12 with L1AlH4 affords the 3,3′-biisoborneol

  3-外型，3'-外切- （1 - [R，1' - [R）-bicamphor（12）从3-获得外，3'-外切- （1 - [R，1' - [R）-bithtiocamphor（3）通过缩合水合肼，然后水解生成的二氢哒嗪11。用NaH脱除12的质子，然后用六氰合铁酸钾（III）处理，得到2,2'-dioxo-3,3'-bibornanylidene 13，而用L1AlH 4还原12则得到3,3'-bi异冰片16。描述了对各种2,2'-双官能3,3'-联萘烷衍生物的进一步相关转化，作为手性配体可能是令人感兴趣的
• Studies of The Reactivity of (1R,1′R)-3-exo, 3′-exo-Bicamphor; Preparation of New 3-exo, 3′-exo-Bibornane Derivatives
  作者：Jean-Olivier Durand

  DOI：10.1055/s-1999-3478

  日期：1999.5

  The preparative conversion of (1R,1′R)-3-exo, 3′-exo-bicamphor (1) in different useful 3-exo, 3′-exo-bibornane derivatives has been explored. The reactivity of bibornane type molecules was controlled by steric factors which made those products recalcitrant towards functionalisation and led to unusual behaviour. Nevertheless the synthesis of the monophosphine alcohol 9 was achieved in 4 steps and in 25% overall yield after a methylenation hydroboration-oxidation methodology applied to (1R,1′R)-3-exo, 3′-exo-bicamphor (1).

  已经探索了 (1R,1'R)-3-exo, 3'-exo-双樟脑 (1) 在不同有用的 3-exo, 3'-exo-联冰片烷衍生物中的制备转化。联冰片烷型分子的反应性受空间因素控制，这使得这些产品难以功能化并导致异常行为。尽管如此，在将亚甲基化硼氢化-氧化方法应用于 (1R,1'R)-3-exo, 3'-exo-bicamphor (1) 后，单膦醇 9 的合成通过 4 个步骤实现，总产率为 25%。
• Stereoselective Oxidative Dimerization of (1<i>R</i>)-Camphor. A Short Synthesis of <i>e</i><i>xo</i>,<i>e</i><i>xo</i><i>‘</i>-3,3‘-Biisoborneol
  作者：James McNulty、Monte J. Millar、Gérald Bernardinelli、Charles W. Jefford

  DOI：10.1021/jo990394g

  日期：1999.7.1