2-cyclopentylprop-2-en-1-ol | 26639-84-9

• 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: 2-cyclopentylprop-2-en-1-ol
• CAS: 26639-84-9
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: WWVOVDAYJIYSFC-UHFFFAOYSA-N

物化性质

• 沸点：
  198.0±9.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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-cyclopentylprop-2-en-1-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以80%的产率得到2-cyclopentylacrylaldehyde
  参考文献：
  名称：

  Total synthesis of spatol and other spatane diterpenes

  摘要：

  Total syntheses of three spatane diterpenes stoechospermol (1), 5(R),15(R),18-trihydroxyspata-13,16(E)-diene (2), and (+)-spatol (3) were accomplished from a common intermediate, diol 7. The total synthesis established as R the absolute configuration at the 15-position in 2. Novel stereospecific transformations of 2,3-epoxy-1,4-diols into vicinal diepoxides were demonstrated and exploited for assembling the sensitive allylic diepoxide in the side chain of spatol. This new synthetic method allows the conversion of both 1,2-threo-2,3-trans- and 1,2-erythro-2,3-trans-2,3-epoxy-1,4-diols into vicinal 1,2-cis-2,3-erythro-1,3-diepoxides. Unexpected stability toward hydroxide anion was found for the allylic diepoxide functional array. This observation provides presumptive evidence that acid catalysis is operative in the epoxide cleaving substitution reaction of spatol by the weakly nucleophilic chloride anion that gives chlorohydrin 4. A proclivity for erythro-selective epoxidation of allylic silyl ethers was found. The utility of C-silyl substituents for reversing this stereoselectivity, i.e., favoring threo-selective epoxidation of allylic silyl ethers, was established.

  DOI：

  10.1021/ja00008a044
• 作为产物：
  描述：

  环戊基乙酸乙酯 在 四氢吡咯 、 sodium tetrahydroborate 、 4-二甲氨基苯甲酸 、 二异丁基氢化铝 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-cyclopentylprop-2-en-1-ol
  参考文献：
  名称：

  烯烃二羰基化合物的催化，对映选择性和高度化学选择性溴环化

  摘要：

  优先选择：胺-硫代氨基甲酸酯催化剂可介导烯烃1,3-二羰基化合物的简便，高效和高度对映选择性溴环化。在双功能催化剂的存在下，溴化反应是化学选择性地发生在烯烃部分，而不是发生在羰基单元α位的碳原子上。

  DOI：

  10.1002/anie.201304107

文献信息

• Cross-Metathesis Reactions of Homoallyl Methyl Malonates with Sterically Hindered Allylic Esters
  作者：Fabio Barile、Mauro Bassetti、Andrea D'Annibale、Renzo Gerometta、Michele Palazzi

  DOI：10.1002/ejoc.201100916

  日期：2011.11

  The methyl malonate esters of 3-buten-1-ol and 2-methyl-3-buten-1-ol can be coupled efficiently to different methallylic esters in the presence of the second-generation Grubbs catalyst to yield trisubstituted olefins by the cross-metathesis reaction. Product selectivity and yields depend on the relative amounts of reagents and to a minor extent on the methallylic ester functional group. Alkyl substituents

  3-丁烯-1-醇和2-甲基-3-丁烯-1-醇的丙二酸甲酯在第二代Grubbs催化剂存在下可与不同的甲基烯丙酯有效偶联，通过交联反应生成三取代烯烃。复分解反应。产物选择性和产率取决于试剂的相对量，并在较小程度上取决于甲基烯丙基酯官能团。烯丙基或孪晶位置的烷基取代基显着影响产物产率和 E/Z 立体选择性。
• Synthetic spirocyclic endoperoxides: new antimalarial scaffolds
  作者：Margherita Brindisi、Sandra Gemma、Sanil Kunjir、Luisa Di Cerbo、Simone Brogi、Silvia Parapini、Sarah D'Alessandro、Donatella Taramelli、Annette Habluetzel、Sofia Tapanelli、Stefania Lamponi、Ettore Novellino、Giuseppe Campiani、Stefania Butini

  DOI：10.1039/c4md00454j

  日期：——

  Here we report the development of a straightforward synthetic procedure for the preparation of spirocyclic endoperoxides as synthetic analogues of the natural product dihydroplakortin. The peroxides presented here are more potent antiplasmodials than dihydroplakortin itself and we proved for the first time their antimalarial activity in vivo.

  在这里，我们报告了制备作为天然产物合成类似物的螺环过氧化物的简单合成方法的进展 二氢铂蛋白。这里介绍的过氧化物比二氢铂蛋白本身和我们首次证明了它们在体内的抗疟疾活性。
• Ruthenium-Catalyzed Alkene–Alkyne Coupling of Disubstituted Olefins: Application to the Stereoselective Synthesis of Trisubstituted Enecarbamates
  作者：Barry M. Trost、James J. Cregg

  DOI：10.1021/ja511911b

  日期：2015.1.21

  The Ru-catalyzed alkene-alkyne coupling reaction has been demonstrated to be an enabling methodology for the synthesis of complex molecules. However, to date, it has been limited to monosubstituted olefins. Herein we report the first general utilization of disubstituted olefins in the Ru-catalyzed alkene-alkyne coupling reaction by employing carbamate directing groups. The products are stereodefined

  Ru催化的烯烃-炔烃偶联反应已被证明是合成复杂分子的一种可行方法。然而，迄今为止，它仅限于单取代的烯烃。在本文中，我们报告了通过使用氨基甲酸酯导向基团在 Ru 催化的烯烃-炔烃偶联反应中首次普遍利用二取代烯烃。产品是立体定义的三取代的烯氨基甲酸酯。讨论了这些结构对复杂氨基环戊醇和 1,2-氨基醇的不对称合成的阐述。
• Carbamate-Catalyzed Enantioselective Bromolactamization
  作者：Yi An Cheng、Wesley Zongrong Yu、Ying-Yeung Yeung

  DOI：10.1002/anie.201504724

  日期：2015.10.5

  A highly facile, efficient, and enantioselective bromolactamization of olefinic amides was effected by a carbamate catalyst and ethanol additive. The amide substrates underwent N‐cyclization predominantly to give a diverse range of enantioenriched bromolactam products containing up to two stereogenic centers.

  氨基甲酸酯催化剂和乙醇添加剂可实现烯烃酰胺的高度简便，高效和对映选择性的溴内酰胺化。酰胺底物主要经过N环化作用，以产生多种对映体富集的溴内酰胺产品，其中最多包含两个立体异构中心。
• Rhodium-Catalyzed Asymmetric Hydroformylation of 1,1-Disubstituted Allylphthalimides: A Catalytic Route to β³-Amino Acids
  作者：Xin Zheng、Bonan Cao、Tang-lin Liu、Xumu Zhang

  DOI：10.1002/adsc.201200960

  日期：2013.3.11

  enantioselective rhodium‐catalyzed hydroformylation of 1,1‐disubstituted allylphthalimides has been developed. By employing chiral ligand 1,2‐bis[(2S,5S)‐2,5‐diphenylphospholano]ethane [(S,S)‐Ph‐BPE], a series of β3‐aminoaldehydes can be prepared with up to 95% enantioselectivity. This asymmetric procedure provides an efficient alternative route to prepare chiral β3‐amino acids and alcohols.

  已经开发出高对映体选择性的铑催化的1,1-二取代的烯丙基邻苯二甲酰亚胺亚甲基化。通过采用手性配体1,2-双[（2-小号，5小号）-2,5- diphenylphospholano]乙烷[（小号，小号）-Ph-BPE]，一系列的β 3 -aminoaldehydes最多可以与制备对映选择性为95％。这种不对称的过程提供了一种有效的替代路线，制备手性β 3 -氨基酸和醇。