(-)-(R)-1-penten-3-ol | 93222-01-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(R)-1-penten-3-ol
• 英文别名: (-)-pent-1-en-3-ol；(R)-pent-1-en-3-ol；(-)-penten-3-ol；R-1-penten-3-ol；(R!)-pent-1-en-3-ol; (-)-ethylvinylcarbinol；(R!)-Pent-1-en-3-ol; (-)-Aethylvinylcarbinol；(3R)-pent-1-en-3-ol
• CAS: 93222-01-6
• 化学式: C₅H₁₀O
• 分子量: 86.1338
• InChiKey: VHVMXWZXFBOANQ-YFKPBYRVSA-N

物化性质

• LogP：
  0.991 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (-)-(R)-1-penten-3-ol 在 N-溴代丁二酰亚胺(NBS) 、 盐酸羟胺 、 sodium hydride 、 potassium carbonate 、 臭氧 、 silver nitrate 、 正丁胺 、 三氟乙酸 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 76.08h， 生成 (3R,8S,9S,10S)-10-methoxyheptadeca-4,6-diyne-3,8,9-triol
  参考文献：
  名称：

  First total synthesis and structure confirmation of diacetylenic polyol (+)-oploxyne B

  摘要：

  The first total synthesis of the natural product (+)-oploxyne B is achieved. The synthesis has led to the confirmation of absolute stereochemistry of the natural product. The natural product displayed cytotoxic activity with IC50 values varying from 16 to 53 mu M in four cancer cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.020
• 作为产物：
  描述：

  1-戊烯-3-醇 生成 (-)-(R)-1-penten-3-ol
  参考文献：
  名称：

  通过脂族克莱森重排的立体定向方法合成3-oxocen-7-ones。（+）-（2 R，8 S）-和（+）-（2 R，8 J）-月桂聚糖的合成

  摘要：

  基于热诱导的克莱森环膨胀作为关键步骤的一般合成策略允许在对映体纯条件下和适当的绝对构型下快速加工月桂聚糖。短序列（九个步骤）构成了通往天然存在的中环醚的新途径。

  DOI：

  10.1016/s0040-4020(01)85577-0

文献信息

• Stereoselective Rh-Catalyzed Hydrogenative Desymmetrization of Achiral Substituted 1,4-Dienes
  作者：Héctor Fernández-Pérez、Joan R. Lao、Anton Vidal-Ferran

  DOI：10.1021/acs.orglett.6b01088

  日期：2016.6.17

  Highly efficient catalytic stereoselective hydrogenative desymmetrization reactions mediated by rhodium complexes derived from enantiopure phosphine–phosphite (P–OP) ligands are described. The highest performing ligand, which contains a TADDOL-derived phosphite fragment [TADDOL = (2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)], presented excellent catalytic properties for the desymmetrization

  描述了由对映体纯膦-亚磷酸酯（P-OP）配体衍生的铑配合物介导的高效催化立体选择性加氢脱对称反应。最高性能的配体，其中包含TADDOL衍生的亚磷酸酯片段[TADDOL =（2,2-二甲基-1,3-二氧戊环-4,5-二基）双（二苯基甲醇）]，具有出色的催化性能，可用于脱甲基一组非手性1,4-二烯，提供了选择性形成多种对映体富集的仲和叔醇的方法（六个实例，最高可达92％ee）。
• A concise total synthesis of enantiomerically pure (+)-cis- and (+)-trans-lauthisan
  作者：Leo A. Paquette、Thomas J. Sweeney

  DOI：10.1021/jo00293a006

  日期：1990.3
• Stereoselectivity in the Rhodium-Catalysed Reductions of Non-Conjugated Dienes
  作者：Bao Nguyen、John M. Brown

  DOI：10.1002/adsc.200900013

  日期：2009.6

  Abstractmagnified imageThe stereochemical course of rhodium‐catalysed addition of hydrogen and catecholborane to bicyclo[2.2.1]heptadiene, and of hydrogen to a range of cyclic dienes has been analysed. For hydroboration, the overall catalytic reaction possesses exo‐selectivity, but the initial step is endo‐selective. For hydrogenation (deuteration), the first step may occur with either exo‐ or endo‐ selectivity, depending on the structure of the diene. This enables a distinction to be made between pathways involving prior dissociation of the diene, and direct addition to the complexed diene without full dissociation. The relative ease of hydrogenation of the first and second double bonds varies markedly with reactant structure, and also depends on the choice of catalyst ligands. For dicyclopentadiene, hydrogenation of the cyclopentene double bond is accompanied by rapid alkene isomerisation, as revealed by deuterium addition. The asymmetric hydrogenation of acyclic skipped meso‐dienes is reported, demonstrating control of relative rates of the two sequential steps, with ees of up to 53% after the first reduction.
• Hayashi, Masahiko; Kaneko, Toshiyuki; Oguni, Nobuki, Journal of the Chemical Society. Perkin transactions I, 1991, # 1, p. 25 - 28
  作者：Hayashi, Masahiko、Kaneko, Toshiyuki、Oguni, Nobuki

  DOI：——

  日期：——
• Directing effects of tethered alkenes in nickel-catalyzed coupling reactions of 1,6-enynes and aldehydes
  作者：Ryan M. Moslin、Karen M. Miller、Timothy F. Jamison

  DOI：10.1016/j.tet.2006.03.122

  日期：2006.8

  Nickel-catalyzed reductive coupling reactions of aldehydes and 1,6-enynes proceed in excellent regioselectivity in the absence of a phosphine, and the use of a monodentate phosphine additive leads to the formation of the opposite regioisomer with equally high selectivity. Both products are the result of the same fundamental mechanism, with the inversion of regioselectivity being the result of stereospecific ligand substitution at the metal center. (c) 2006 Elsevier Ltd. All rights reserved.