(S)-(-)-hex-5-en-3-ol | 62959-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(-)-hex-5-en-3-ol
• 英文别名: (4S)-1-hexen-4-ol；(S)-hex-5-en-3-ol；(+)(S)-hexen-(1)-ol-(4)；(S)-Hex-5-en-3-ol；5-Hexen-3-ol, (S)-；(3S)-hex-5-en-3-ol
• CAS: 62959-96-0
• 化学式: C₆H₁₂O
• 分子量: 100.161
• InChiKey: UOGFCIYBLKSQHL-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (S)-(-)-hex-5-en-3-ol 生成 3-羟基戊酸
  参考文献：
  名称：

  Levene; Haller, Journal of Biological Chemistry, 1928, vol. 76, p. 421

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-(2-hydroxypent-4-enyl) 4-methylbenzenesulfonate 在 copper(l) iodide 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.17h， 生成 (S)-(-)-hex-5-en-3-ol
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Novel Carbocyclic Influenza Neuraminidase Inhibitors

  摘要：

  A series of influenza neuraminidase inhibitors with the cyclohexene scaffold containing lipophilic side chains have been synthesized anti evaluated for influenza A and B neuraminidase inhibitory activity. The size and geometry of side chains have been modified systematically in order to investigate structure-activity relationships of this class of compounds. The X-ray crystal structures of several analogues complexed with neuraminidase revealed that the lipophilic side chains bound to the hydrophobic pocket consisted of Glu276, Ala246, Arg224, and Ile222 of the enzyme active site. The structure-activity relationship studies of this series have also demonstrated remarkably different inhibitory potency between influenza A and B neuraminidase. This indicated that the lipophilic side chains had quite different hydrophobic interactions with influenza A and B neuraminidase despite their complete homology in the active site. Influenza B neuraminidase appeared to be much more sensitive toward the increased steric bulkiness of inhibitors compared to influenza A neuraminidase. From the extensive structure-activity relationship investigation reported in this article, GS 4071 emerged as one of the most potent influenza neuraminidase inhibitors against both influenza A and B strains.

  DOI：

  10.1021/jm980162u

文献信息

• Enantio- and Diastereoselective Synthesis of 1,5-<i>syn</i>-(<i>Z</i>)-Amino Alcohols via Imine Double Allylboration: Synthesis of <i>trans</i>-1,2,3,6-Tetrahydropyridines and Total Synthesis of Andrachcine
  作者：Christophe Allais、William R. Roush

  DOI：10.1021/acs.orglett.7b00995

  日期：2017.5.19

  A stereoselective synthesis of trans-1,2,3,6-tetrahydropyridines 8 is described. This synthesis proceeds via intramolecular Mistunobu reactions of 1,5-syn-(Z)-amino alcohols 7, which were prepared by a highly diastereo- and enantioselective double-allylboration reaction of aldehyde 5 and silylimine 6. The chiral bifunctional γ-borylallylborane 9E was generated in situ by hydroboration of allene 3 with

  描述了反式-1,2,3,6-四氢吡啶8的立体选择性合成。这种合成经由1,5-分子内Mistunobu反应所得顺式（ - Ž） -氨基醇7，其通过醛的高度diastereo-和不对称双allylboration反应制备5和silylimine 6。手性双官能γ-borylallylborane 9 Ë由丙二烯的硼氢化原位产生3与（diisopinocampheyl）硼烷4。该策略已应用于雄激素1的全合成，因此可以确定天然产品的绝对和相对构型。
• STABLE BORANE REAGENTS AND METHODS FOR THEIR USE
  申请人：MeReddy Venkatram R.

  公开号：US20080287708A1

  公开（公告）日：2008-11-20

  The invention provides methods for storing boranes (e.g. B-allyldiisopinocampheylborane). The invention also provides stable compositions comprising boranes, as well as methods for carrying out allylboration at high temperature and/or in the presence of water.

  该发明提供了存储硼烷类化合物（例如B-烯基二异薄脑基硼烷）的方法。该发明还提供了含硼烷类化合物的稳定组合物，以及在高温和/或水存在下进行烯基硼化反应的方法。
• Synthesis and Biological Evaluation of Dichlorinated Chondramide Derivatives
  作者：Dominic Becker、Uli Kazmaier

  DOI：10.1002/ejoc.201500369

  日期：2015.7

  Straightforward synthetic protocols for the synthesis of new ethyl-substituted dichlorinated chondramides with different methyl-substitution patterns in the polyketide fragment have been developed. The methyl groups at the ϵ-position can be removed completely without a significant influence on the biological activity. In contrast, after removal of the α-methyl group, a significant drop in activity

  已经开发了用于合成在聚酮化合物片段中具有不同甲基取代模式的新型乙基取代二氯化软骨素的简单合成方案。ϵ-位的甲基可以完全去除，对生物活性没有显着影响。相反，去除α-甲基后，观察到活性显着下降。如果 α-甲基的构型反转，也会观察到这一点。
• Chiral synthesis via organoboranes. 24. B-allylbis(2-isocaranyl)borane as a superior reagent for the asymmetric allylboration of aldehydes
  作者：Herbert C. Brown、Ramnarayan S. Randad、Krishna S. Bhat、Marek Zaidlewicz、Uday S. Racherla

  DOI：10.1021/ja00162a047

  日期：1990.3

  Le reactif utilise : l'(allyl bis-isocaranyl) borane est prepare a partir du (+)-carene-2 obtenu par isomerisation du (+)-carene-3

  Le reactif利用：l'(allyl bis-isocaranyl) borane est prepare a partir du (+)-carene-2 obtenu par isomerisation du (+)-carene-3
• Stereospecific synthesis of a GS 4104 metabolite: Determination of absolute sterochemistry and influenza neuraminidase inhibitory activity
  作者：Willard Lew、Paul A. Escarpe、Dirk B. Mendel、David J. Sweeny、Choung U. Kim

  DOI：10.1016/s0960-894x(99)00479-5

  日期：1999.10

  The total synthesis for the determination of the absolute stereochemistry of a GS 4104 metabolite 3 is described. In addition, the influenza neuraminidase inhibitory activity of 3 and related intermediates are reported.

  描述了用于确定GS 4104代谢物3的绝对立体化学的全合成。另外，据报道有3种流感病毒神经氨酸酶抑制活性及相关中间体。