(-)-(1R,2S)-2-benzylcyclopentanol | 135357-02-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (-)-(1R,2S)-2-benzylcyclopentanol
• 英文别名: trans-2-Benzylcyclopentanol；2i-trans；trans-2Benzylcyclopentanol；(1R,2S)-2-benzylcyclopentan-1-ol
• CAS: 135357-02-7
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: OWWHRTUEIUFQKM-NWDGAFQWSA-N

物化性质

• 沸点：
  287.2±9.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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,2S)-2-benzylcyclopentanol 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到(-)-(1R,2S)-2-benzylcyclopentyl acetate
  参考文献：
  名称：

  (−)-Sparteine-Mediated Asymmetric Intramolecular Carbolithiation of Alkenes: Synthesis of Enantiopure Cyclopentanes with Three Consecutive Stereogenic Centers

  摘要：

  An asymmetric intramolecular carbolithiation reaction was developed by combining the (-)-sparteine-mediated enantiotopos-differentiating deprotonation and the anionic 5-exo-trig cyclization. Achiral 6-phenyl-hex-5-enyl carbamates were efficiently cyclized furnishing regio-, diastereo- (dr > 99:1),and enantioselectively (er >98:2) 1,2-trans-substituted cyclopentanes. The intermediate primary benzylic Lithium-carbanion pairs were - in spite of their configurative lability - diastereoselectively substituted by versatile electrophiles creating a third consecutive stereogenic center. Additionally, some 4-functionalized 6-phenylhex-5-enyl carbamates were also cyclized in high yield to provide enantiomericaliy pure cyclopentanes incorporating three adjacent stereogenic centers.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<1860::aid-hlca1860>3.0.co;2-8
• 作为产物：
  描述：

  Diisopropyl-carbamic acid (1R,2S,3S)-2-benzyl-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl ester 在 erythritol tetranitrate 、 四丁基氟化铵 、 二异丁基氢化铝 、 三乙基硼氢化锂 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 (-)-(1R,2S)-2-benzylcyclopentanol
  参考文献：
  名称：

  Enantioselective carbanion cyclization of 5-alkenyl carbamates induced by asymmetric lithiation with s-butyllithium/(−)-sparteine system

  摘要：

  Treatment of (E)-6-phenyl-5-hexenyl carbamates with s-BuLi /(-)-sparteine is shown to afford the trans-1,2-disubstituted cyclopentane derivatives in high % ee, along with the bicyclo[3.1.0]hexanes (bicyclization products). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02233-3

文献信息

• Dual Activation of Unsaturated Amides with Schwartz's Reagent: A Diastereoselective Access to Cyclopentanols and N,O‐Dimethylcyclopentylhydroxylamines.
  作者：Aurélien Coelho、Mahasoa‐Salina Souvenir Zafindrajaona、Alexis Vallée、Jean‐Bernard Behr、Jean‐Luc Vasse

  DOI：10.1002/chem.202103789

  日期：2022.1.13

  The concomitant generation of a nucleophilic and an electrophilic site from unsaturated Weinreb amide by using Cp2Zr(H)Cl) as the unique reagent was developed to promote a cyclisation reaction. The access to trans-2-substituted cyclopentanols or cyclopentylhydroxylamines can be selectively driven by a judicious choice of the cyclisation promotor. An access to cis-3-substituted is also described.

  通过使用 Cp 2 Zr(H)Cl) 作为独特的试剂，开发了从不饱和 Weinreb 酰胺中同时产生亲核位点和亲电位点以促进环化反应。对环化促进剂的明智选择可以选择性地驱动获得反式-2-取代的环戊醇或环戊基羟胺。还描述了对顺式-3-取代的访问。
• Asymmetric reduction of prochiral cycloalkenones. The influence of exocyclic alkene geometry
  作者：Alison F. Simpson、Corinna D. Bodkin、Craig P. Butts、Mark A. Armitage、Timothy Gallagher

  DOI：10.1039/b004540n

  日期：——

  The asymmetric reduction of a series of prochiral enones of general structure 1 using the Corey oxazaborolidine 2, leading to enantiomerically enriched allylic cycloalkanols 3 is described. The influence of alkene geometry on both the sense (Rvs. S) and efficiency (% ee) of the asymmetric reduction process has been probed for two systems, (E)- and (Z)-4 and (E)- and (Z)-7, based on cyclohexanone and cyclopentanone respectively. The absolute stereochemistry of the cyclopentyl derivative (E)-8 has been established by X-ray crystallographic analysis of carbamate 10. The ability to assign an absolute configuration to allylic alcohols 3, based on the NMR methods described earlier by Riguera, has been evaluated.

  本研究介绍了使用科里噁唑硼烷 2 对一系列具有一般结构 1 的手性烯酮进行不对称还原，从而得到对映体富集的烯丙基环烷醇 3 的过程。在分别基于环己酮和环戊酮的 (E)- 和 (Z)-4 和 (E)- 和 (Z)-7 两个系统中，探究了烯烃几何形状对不对称还原过程的意义 (Rvs. S) 和效率 (% ee) 的影响。通过对氨基甲酸酯 10 进行 X 射线晶体分析，确定了环戊基衍生物 (E)-8 的绝对立体化学结构。根据 Riguera 早先描述的核磁共振方法，对分配烯丙基醇 3 绝对构型的能力进行了评估。
• Seemayer, R.; Schneider, M. P., Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 5, p. 171 - 174
  作者：Seemayer, R.、Schneider, M. P.

  DOI：——

  日期：——
• (−)-Sparteine-Mediated Asymmetric Intramolecular Carbolithiation of Alkenes: Synthesis of Enantiopure Cyclopentanes with Three Consecutive Stereogenic Centers
  作者：Dieter Hoppe、Michael J. Woltering、Martin Oestreich、Roland Fröhlich

  DOI：10.1002/(sici)1522-2675(19991110)82:11<1860::aid-hlca1860>3.0.co;2-8

  日期：1999.11.10

  An asymmetric intramolecular carbolithiation reaction was developed by combining the (-)-sparteine-mediated enantiotopos-differentiating deprotonation and the anionic 5-exo-trig cyclization. Achiral 6-phenyl-hex-5-enyl carbamates were efficiently cyclized furnishing regio-, diastereo- (dr > 99:1),and enantioselectively (er >98:2) 1,2-trans-substituted cyclopentanes. The intermediate primary benzylic Lithium-carbanion pairs were - in spite of their configurative lability - diastereoselectively substituted by versatile electrophiles creating a third consecutive stereogenic center. Additionally, some 4-functionalized 6-phenylhex-5-enyl carbamates were also cyclized in high yield to provide enantiomericaliy pure cyclopentanes incorporating three adjacent stereogenic centers.
• Enantioselective carbanion cyclization of 5-alkenyl carbamates induced by asymmetric lithiation with s-butyllithium/(−)-sparteine system
  作者：Katsuhiko Tomooka、Nobuyuki Komine、Tomoya Sasaki、Hideo Shimizu、Takeshi Nakai

  DOI：10.1016/s0040-4039(98)02233-3

  日期：1998.12

  Treatment of (E)-6-phenyl-5-hexenyl carbamates with s-BuLi /(-)-sparteine is shown to afford the trans-1,2-disubstituted cyclopentane derivatives in high % ee, along with the bicyclo[3.1.0]hexanes (bicyclization products). (C) 1998 Elsevier Science Ltd. All rights reserved.