2-环戊基亚基-环戊醇 | 6261-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-环戊基亚基-环戊醇
• 英文名称: (+/-)-2-Cyclopentylidenecylopenta-1-ol
• 英文别名: 2-Cyclopentylidenecyclopentanol；bicyclopentyliden-2-ol；cyclopentylidene-cyclopentanol；(+/-)-1-Cyclopentyliden-cyclopentanol-(2)；2-Cyclopentyliden-1-cyclopentanol；2-Cyclopentyliden-cyclopentanol；Cyclopentanol, 2-cyclopentylidene-；2-cyclopentylidenecyclopentan-1-ol
• CAS: 6261-30-9
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: QDNVHPQZFWWZNO-UHFFFAOYSA-N

物化性质

• 熔点：
  53 °C
• 沸点：
  87 °C(Press: 3 Torr)
• 密度：
  0.99886 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  2-环戊基亚基-环戊醇 、 硫酸二甲酯 生成 (+-)-2-Methoxy-1-cyclopentyliden-cyclopentan
  参考文献：
  名称：

  Le Guillanton,G., Bulletin de la Societe Chimique de France, 1963, p. 611 - 619

  摘要：

  DOI：
• 作为产物：
  描述：

  5-cyclopent-1-enyl-valeryl chloride 在 二硫化碳 、 lithium aluminium tetrahydride 、 三氯化铝 作用下， 生成 2-环戊基亚基-环戊醇
  参考文献：
  名称：

  Northwest Africa 032: Product of lunar volcanism

  摘要：

  Abstract— Mineralogy, major element compositions of minerals, and elemental and oxygen isotopic compositions of the whole rock attest to a lunar origin of the meteorite Northwest Africa (NWA) 032, an unbrecciated basalt found in October 1999. The rock consists predominantly of olivine, pyroxene and chromite phenocrysts, set in a crystalline groundmass of feldspar, pyroxene, ilmenite, troilite and trace metal. Whole‐rock shock veins comprise a minor, but ubiquitous portion of the rock. Undulatory to mosaic extinction in olivine and pyroxene phenocrysts and micro‐faults in groundmass and phenocrysts also are attributed to shock.Several geochemical signatures taken together indicate unambiguously that NWA 032 originated from the Moon. The most diagnostic criteria include whole‐rock oxygen isotopic composition and ratios of Fe/Mn in the whole rock, olivine, and pyroxene. A lunar origin is documented further by the presence of Fe‐metal, troilite, and ilmenite; zoning to extremely Fe‐rich compositions in pyroxene; the ferrous oxidation state of all Fe in pyroxene; and the rare earth element (REE) pattern with a well‐defined negative europium anomaly. This rock is similar in major element chemistry to basalts from Apollo 12 and 15, but is enriched in light REE and has an unusually high Th/Sm ratio. Some Apollo 14 basalts yield a closer match to NWA 032 in REE patterns, but have higher concentrations of Al2O3. Ar‐Ar step release results are complex, but yield a whole‐rock age of ˜2.8 Ga, suggesting that NWA 032 was extruded at 2.8 Ga or earlier. This rock may be the youngest sample of mare basalt collected to date. Noble gas concentrations combined with previously collected radionuclide data indicate that the meteorite exposure history is distinct from currently recognized lunar meteorites. In short, the geochemical and petrographic features of NWA 032 are not matched by Apollo or Luna samples, nor by previously identified lunar meteorites, indicating that it originates from a previously unsampled mare deposit.Detailed assessment of petrographic features, olivine zoning, and thermodynamic modelling indicate a relatively simple cooling and crystallization history for NWA 032. Chromite‐spinel, olivine, and pyroxene crystallized as phenocrysts while the magma cooled no faster than 2 °C/h based on the polyhedral morphology of olivine. Comparison of olivine size with crystal growth rates and preserved Fe‐Mg diffusion profiles in olivine phenocrysts suggest that olivine was immersed in the melt for no more than 40 days. Plumose textures in groundmass pyroxene, feldspar, and ilmenite, and Fe‐rich rims on the phenocrysts formed during rapid crystallization (cooling rates ˜20 to 60 °C/h) after eruption.

  DOI：

  10.1111/j.1945-5100.2002.tb00822.x

文献信息

• The Palladium-Catalyzed Aerobic Kinetic Resolution of Secondary Alcohols: Reaction Development, Scope, and Applications
  作者：David C. Ebner、Jeffrey T. Bagdanoff、Eric M. Ferreira、Ryan M. McFadden、Daniel D. Caspi、Raissa M. Trend、Brian M. Stoltz

  DOI：10.1002/chem.200902172

  日期：2009.12.7

  and tert‐butyl alcohol greatly enhances reaction rates, promoting rapid resolutions. The use of chloroform as solvent allows the use of ambient air as the terminal oxidant at 23 °C, resulting in enhanced catalyst selectivity. These improved reaction conditions have permitted the successful kinetic resolution of benzylic, allylic, and cyclopropyl secondary alcohols to high enantiomeric excess with good‐to‐excellent

  已经开发出第一个钯催化的仲醇对映选择性氧化反应，利用容易获得的二胺（-）-金雀花石作为手性配体，分子氧作为化学计量氧化剂。关于碱基和氢键供体作用的机制见解导致了对原始系统的一些改进。也就是说，碳酸铯和叔丁醇的添加大大提高了反应速率，促进了快速分辨率。使用氯仿作为溶剂允许在 23 °C 下使用环境空气作为终端氧化剂，从而提高催化剂选择性。这些改进的反应条件使得能够以良好至优异的选择性因子成功地将苄基、烯丙基和环丙基仲醇动力学拆分为高对映体过量。该催化剂体系也已应用于内消旋二醇的去对称化，提供高产率的对映体富集的羟基酮。
• Morphology‐Tuned Activity of Ru/Nb ₂ O ₅ Catalysts for Ketone Reductive Amination
  作者：Wanjun Guo、Tao Tong、Xiaohui Liu、Yong Guo、Yanqin Wang

  DOI：10.1002/cctc.201900335

  日期：2019.8.21

  durability test. In addition, this catalyst can be extended to a series of aldehydes/ketones. Further comprehensive characterizations (XPS analysis and CO‐adsorption DRIFT) reveal that the electronic effect of Ru species can be ruled out; instead, the activity of the catalyst is strongly influenced by the geometric effect. Layered Nb2O5 material possesses the highest surface area, resulting in the highest

  胺是天然产物和药物中的重要化合物。特别是，环戊胺是广泛用于生产农药，化妆品和药品的增值化学品之一。在这项工作中，使用三种具有不同Nb 2 O 5形态的Ru / Nb 2 O 5催化剂在温和的反应条件下（90°C，2 MPa H 2）还原胺化环戊酮，其中1％Ru / Nb 2 Ø 5-L催化剂表现出最佳性能，环戊胺的收率达到84％。即使在耐久性试验中运行5次后，该催化体系也很稳定并且没有明显的失活。另外，该催化剂可以扩展为一系列醛/酮。进一步的综合表征（XPS分析和CO吸附DRIFT）表明，可以排除Ru物种的电子效应。相反，催化剂的活性受到几何效应的强烈影响。层状Nb 2 O 5该材料具有最高的表面积，导致最大的Ru分散，因此显示出最高的催化活性。原位DRIFT-MS技术也用于揭示和理解反应机理。发现Ru物种在活化羰基中起关键作用。这项研究说明了Ru / Nb 2 O 5层催化剂在胺的合成中
• [EN] CYCLOPROPANATION PROCESS<br/>[FR] PROCÉDÉ DE CYCLOPROPANATION
  申请人：GIVAUDAN SA

  公开号：WO2009023980A1

  公开（公告）日：2009-02-26

  A method for the preparation of cyclopropyl carbinols by cyclopropanation of unsaturated alcoholates, utilising a reagent system selected from (A) magnesium metal and dibromomethane, and (B) dibromomethane and a tertiary Grignard reagent, the reaction being carried out in the presence of an ether solvent. The process is useful, for example, for the preparation of ingredients for the flavour and fragrance industry.

  一种通过使用选自(A)镁金属和二溴甲烷，以及(B)二溴甲烷和三级格氏试剂的试剂体系，通过环丙烷化不饱和醇酸盐来制备环丙基醇的方法，该反应在醚溶剂存在下进行。该过程可用于为香料和香精行业的成分制备。
• 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。
• Cyclopentylidene-cyclopentanol in pereumery
  申请人：Quest International B.V.

  公开号：US05776884A1

  公开（公告）日：1998-07-07

  The invention relates to the use of 2-cyclopentylidene-cyclopentanol as fragrance and flavour material. The compound has an indolic odour and is therefore very useful for replacing indole in perfumes and flavourings. Unlike indole it is stable to light and in alkaline media and gives no discolouration.

  该发明涉及将2-环戊基环戊烯醇用作香料和调味品原料。该化合物具有吲哚气味，因此非常适合用于替代香水和调味品中的吲哚。与吲哚不同，它对光稳定，在碱性介质中也稳定，并且不会变色。