5-辛炔-3-醇 | 53723-18-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 5-辛炔-3-醇
• 英文名称: (+/-)-5-octyn-3-ol
• 英文别名: Oct-5-in-3-ol；5-Octyn-3-ol；oct-5-yn-3-ol
• CAS: 53723-18-5
• 化学式: C₈H₁₄O
• mdl: MFCD00041595
• 分子量: 126.199
• InChiKey: GGXQZVKQXYOPTF-UHFFFAOYSA-N

物化性质

• 熔点：
  -39°C (estimate)
• 沸点：
  74-75°C 12mm
• 密度：
  0.8537 (estimate)
• 闪点：
  74-75°C/12mm
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，未有已知危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• 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

安全信息

• 海关编码：
  2905290000
• 安全说明：
  S24/25

反应信息

• 作为反应物：
  描述：

  5-辛炔-3-醇 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以83%的产率得到(+/-)-5-(E)-octen-3-ol
  参考文献：
  名称：

  Biocatalytic oxidative kinetic resolution of sec-alcohols: stereocontrol through substrate-modification

  摘要：

  Whole lyophilised cells of Rhodococcus ruber DSM 44541 were employed for the oxidative kinetic resolution of sec-alcohols using acetone as hydrogen acceptor. The enantioselectivity of this process could be controlled effectively by introducing C-C multiple bonds into substrates, which were inefficiently recognised, in particular short-chain (omega-1)-alcohols and (omega-2)-analogs. Thus, the enantioselectivities of rac-2-pentanol (E= 16.8) and rac-3-octanol (E= 13.3) were significantly improved by introducing a C=C bond adjacent to the alcohol moiety to give racemic (E)-pent-3-en-2-ol and 4-(E)-octen-3-ol, which were resolved with excellent selectivities (E >100 and 50, respectively). In addition, it was found that high stereodifferentiation between the E- and Z-configured double bonds occurred, as the corresponding (Z)-isomers were not converted. Similar selectivity-enhancing effects were observed with acetylenic analogs. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00795-4

文献信息

• Stereoselective synthesis of 1,2,4-triols via intramolecular bis-silylation of CarbonCarbon triple bonds followed by hydrogenation
  作者：Masahiro Murakami、Hideaki Oike、Mitsuru Sugawara、Michinori Suginome、Yoshihiko Ito

  DOI：10.1016/s0040-4020(01)89908-7

  日期：1993.5

  new strategy for the stereoselective synthesis of 1,2,4-triols has been developed. An alkyne tethered to a disilanyl group, upon treatment with palladium acetate and tert-alkyl isocyanide, furnished an exocyclic bis-silylated olefin. Subsequent hydrogenation took place from the less-hindered side of the ring producing cis-disubstituted oxasilolane. Oxidation of the two CSi bonds of the hydrogenated

  已经开发了1,2,4-三醇立体选择性合成的新策略。在用乙酸钯和叔烷基异氰化物处理后，被束缚至二硅烷基的炔烃提供了环外双甲硅烷基化的烯烃。随后从环的受阻较弱的一侧进行氢化，生成顺式-二取代的氧杂硅烷基。氢化恶唑烷烃的两个CSi键的氧化导致1,2,4-三醇的立体和区域确定的合成。
• Hydrogenation Promoter, Hydrogenation Catalyst, and Process for Producing Alkene Compound
  申请人：Hori Junichi

  公开号：US20080033221A1

  公开（公告）日：2008-02-07

  A hydrogenation promoter of the present invention is produced by reacting an alkyne compound or an alkene compound, a palladium compound represented by a general formula Pd(II)X j L k (where L represents a monodentate ligand or a polydendate ligand other than a phosphorus-containing ligand (when two or more Ls are present in the compound, the Ls may be the same or different), X represents an anionic group, j represents a value determined according to the valence of X so that X j has a valence of −2 as a whole, and k represents an integer in the range of 0 to 4), and a base in an organic solvent. Specifically, The hydrogenation promoter of the invention includes palladium nanoparticles containing the alkyne compound or the alkene compound as an agglomeration-preventing agent.

  本发明的氢化促进剂是通过在有机溶剂中反应炔烃化合物或烯烃化合物、由一般式Pd(II)XjLk表示的钯化合物(其中L表示单齿配体或不含磷的多齿配体（当化合物中存在两个或两个以上的L时，L可以相同也可以不同），X表示阴离子基团，j表示根据X的价确定的值，使Xj整体价为-2，k表示0到4之间的整数)，以及碱的反应产生的。具体来说，本发明的氢化促进剂包括含有炔烃化合物或烯烃化合物作为凝聚抑制剂的钯纳米粒子。
• 3-(Alkynylalkyloxy) Cephalosporins
  申请人：ELI LILLY AND COMPANY

  公开号：EP0168222A2

  公开（公告）日：1986-01-15

  3-(Alkynylelkyloxy)cephalosporin antibiotics and the intermediates therefor are disclosed. Pharmaceutical compositions for the antibiotics are also disclosed.

  本研究公开了 3-(烷基炔基氧基)头孢菌素类抗生素及其中间体。还公开了这些抗生素的药物组合物。
• Synthesis of Carbocyclic and Heterocyclic Fused Quinolines by Cascade Radical Annulations of Unsaturated <i>N</i>-Aryl Thiocarbamates, Thioamides, and Thioureas
  作者：Wu Du、Dennis P. Curran

  DOI：10.1021/ol0344319

  日期：2003.5.1

  [GRAPHICS]Tandem radical cyclizations of suitably substituted N-aryl thiocarbamates, thioamides, and thioureas are induced by exposure to tris(trimethylsilyl)silane (TTMSH) and UV light and provide furoquinolines, isofuroquinolines, cyclopentaquinolines, indoloquinollnes, and related ring systems. The intermediacy of an alpha-thioalkylamino radical, which is the synthetic equivalent of an imidoyl radical, is invoked.
• Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp
  作者：Kevin Burgess、Lee D. Jennings

  DOI：10.1021/ja00016a032

  日期：1991.7

  Competition experiments and measurements of enantioselectivities were used to develop a simple active-site model (Figure 1) for resolutions of beta-hydroxy-alpha-methylene carbonyl compounds III via acyl transfers mediated by lipase from Pseudomonas sp. (AK). Further experiments were used to test and refine this model with respect to resolutions of allylic, propargylic, homopropargylic, and other alcohols (Tables I-IV, respectively). The model proved extremely reliable for predicting the sense of the asymmetric induction, and the combined data collected in this paper give an indication of what structural features of the substrates can be correlated with high enantioselectivities in these resolutions. Furthermore, the results account for the conspicuous reversal of enantioselectivity previously observed in resolutions of gamma-hydroxy-alpha,beta-unsaturated esters 35. Kinetic resolutions of two substrates (allenol 14 and dienol 9) via asymmetric epoxidations were performed for comparison with the methodology presented in this paper.

表征谱图