(1R,3aR,6aR)-octahydro-1-pentalenol | 612546-41-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3aR,6aR)-octahydro-1-pentalenol
• 英文别名: (1R)-octahydropentalen-1-ol；exo,cis-Bicyclo[3.3.0]octan-2-ol；(1R,3AR,6aR)-octahydropentalen-1-ol；(1R,3aR,6aR)-1,2,3,3a,4,5,6,6a-octahydropentalen-1-ol
• CAS: 612546-41-5
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: AOONMBCPMGBOBG-BWZBUEFSSA-N

物化性质

• 沸点：
  209.7±8.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,3aR,6aR)-octahydro-1-pentalenol 在 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 64.0h， 生成 N-[(1S,3aR,6aR)-octahydro-1-pentalenyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  关于N-甲苯磺酰基氮丙啶的α-锂化重排：机理和合成方面

  摘要：

  进行了详细的研究，使用仲丁基锂（有和没有添加（-）-天冬氨酸和TMEDA等配体）对五个环烯N-甲苯磺酰基（甲苯磺酰基）氮丙啶进行重排。烯丙基磺酰胺是环戊烯和环己烯氮丙啶的主要产物，而双环磺酰胺是从环庚烯和环辛烯氮丙啶获得的。在大多数情况下，对甲苯磺酰胺（TsNH 2）作为副产品生产，并就其形成机理进行了机械解释。据信，这些反应涉及α-锂化为锂化的氮丙啶，然后可以通过两个途径分配：（i）通过CH插入反应重排为烯丙基或双环磺酰胺，或（ii）通过仲丁基锂的攻击而还原为烷基化为烯烃。和随后消除TsNH 2。在（-）-天冬氨酸反应中，生成的产物的ee为38-66％，不对称感应的感觉涉及S-氮丙啶立体中心的锂化。这与用环氧化物观察到的相反。

  DOI：

  10.1016/j.tet.2003.09.024
• 作为产物：
  描述：

  endo-bicyclo<3.2.1>oct-8-yl tosylate 生成 (1R,3aR,6aR)-octahydro-1-pentalenol
  参考文献：
  名称：

  GROB, C. A.;WALDNER, A.;ZUTTER, U., HELV. CHIM. ACTA, 1984, 67, N 3, 717-729

  摘要：

  DOI：

文献信息

• The search for an easily-prepared sparteine surrogate
  作者：Vera M. Foley、Rafael Cano、Gerard P. McGlacken

  DOI：10.1016/j.tetasy.2016.09.001

  日期：2016.12

  (-)-Sparteine has proven itself to be a highly efficient and versatile ligand. However, in recent years it has become difficult to source. In addition the (+)-enantiomer is also not readily available. Here we report a suite of chiral diamines as potential sparteine surrogates. Chiral trans-1,2-diaminocyclohexane is commercially available in both enantiomeric forms and the parent structure can be easily modified. New (and known) chiral diamines have been tested in the asymmetric silylation of N-Boc pyrrolidine, N-Boc piperidine, the alpha-alkylation of dimethylhydrazones and in the rearrangement of meso-epoxides. While none match the selectivity of the highly evolved natural product, there is certainly potential for this class of diamine ligands to perform in a diverse set of asymmetric transformations. (C) 2016 Elsevier Ltd. All rights reserved.

  (-)-Sparteine已被证明是一种高效且多用途的配体。然而，近年来，它变得难以获取。此外，(+)-对映体也不易获得。在此，我们报告了一系列手性二胺作为潜在的 sparteine 代用品。手性反式-1,2-二氨基环己烷的两种对映体形式均可从市场上获得，且其母体结构易于修改。我们测试了新型（和已知）的手性二胺在 N-Boc 吡咯烷、N-Boc 哌啶的不对称硅化，二甲基肼的α-烷基化以及间型环氧化物重排中的表现。虽然没有能够匹配高度进化的天然产物的选择性，但这类二胺配体在一系列不对称转化中表现潜力的确值得肯定。 (E) 2016 Elsevier 有限公司。保留所有权利。
• Synthesis, SAR and biological evaluation of 1,6-disubstituted-1H-pyrazolo[3,4-d]pyrimidines as dual inhibitors of Aurora kinases and CDK1
  作者：Jean-Yves Le Brazidec、Angela Pasis、Betty Tam、Christina Boykin、Cheryl Black、Deping Wang、Gisela Claassen、Jer-Hong Chong、Jianhua Chao、Junhua Fan、Khanh Nguyen、Laura Silvian、Leona Ling、Lin Zhang、Michael Choi、Min Teng、Nuzhat Pathan、Shuo Zhao、Tony Li、Art Taveras

  DOI：10.1016/j.bmcl.2012.01.019

  日期：2012.3

  Since the early 2000s, the Aurora kinases have become major targets of oncology drug discovery particularly Aurora-A and Aurora-B kinases (AKA/AKB) for which the selective inhibition in cells lead to different phenotypes. In addition to targeting these Aurora kinases involved in mitosis, CDK1 has been added as a primary inhibition target in hopes of enhancing the cytotoxicity of our chemotypes harboring the pyrazolopyrimidine core. SAR optimization of this series using the AKA, AKB and CDK1 biochemical assays led to the discovery of the compound 7h which combines strong potency against the 3 kinases with an acceptable microsomal stability. Finally, switching from a primary amide to a two-substituted pyrrolidine amide gave rise to compound 15a which exhibited the desired AKA/CDK1 inhibition phenotype in cells but showed moderate activity in animal models using HCT116 tumor cell lines. (C) 2012 Elsevier Ltd. All rights reserved.
• α-Lithiation-rearrangement of N-toluenesulfonyl aziridines with sec-butyllithium and (−)-sparteine: opposite sense of asymmetric induction to epoxides
  作者：Peter O'Brien、Clare M Rosser、Darren Caine

  DOI：10.1016/s0040-4039(03)01677-0

  日期：2003.8

  The alpha-lithiation rearrangement of three cyclic N-toluenesulfonyl (tosyl) aziridines has been carried out using sec-butyl-lithium/(-)-sparteine. In each case, it was established that preferential lithiation of the S-aziridine stereocentre occurred. This is the opposite sense of asymmetric induction to that observed with epoxides. (C) 2003 Elsevier Ltd. All rights reserved.
• BROWN, H. C.;JAGT, D. L. V.;ROTHBERG, I.;HAMMAR, W. J.;KAWAKAMI, J. H., J. ORG. CHEM., 1985, 50, N 12, 2179-2188
  作者：BROWN, H. C.、JAGT, D. L. V.、ROTHBERG, I.、HAMMAR, W. J.、KAWAKAMI, J. H.

  DOI：——

  日期：——
• KIRMSE W.; STREU J., J. ORG. CHEM., 52,(1987) N 4, 515-521
  作者：KIRMSE W.、 STREU J.

  DOI：——

  日期：——