(S)-癸烷-3-醇 | 120523-17-3

• 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: (S)-癸烷-3-醇
• 英文名称: (S)-3-decanol
• 英文别名: (3S)-decan-3-ol；3-decanol；(S)-decan-3-ol
• CAS: 120523-17-3
• 化学式: C₁₀H₂₂O
• 分子量: 158.284
• InChiKey: ICEQLCZWZXUUIJ-JTQLQIEISA-N

物化性质

• 保留指数：
  1206

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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)-癸烷-3-醇 在 吡啶 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 生成
  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
• 作为产物：
  描述：

  顺-2-壬烯-1-醇 在 ((1S,2R,5S)-2-i-Pr-5-Me-cyclohex-1-yl)Cp)2TiCl₂ titanium(IV) isopropylate 、 叔丁基过氧化氢 、 锰 、 copper(l) iodide 、 L-(+)-酒石酸二乙酯 、 1,4-环己二烯 、 2,4,6-collidine hydrochloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 (S)-癸烷-3-醇
  参考文献：
  名称：

  Titanocene-Catalyzed Regiodivergent Epoxide Openings

  摘要：

  The first regiodivergent opening of unbiased epoxides providing the ring-opened products in high enantiomeric excess from racemic and exceptionally high enantiomeric excess from enantioenriched substrates in a double asymmetric process has been devised. It constitutes a more general case of the very important enantioselective openings of meso-epoxides.

  DOI：

  10.1021/ja0686211

文献信息

• 3,3‘-Diphosphoryl-1,1‘-bi-2-naphthol−Zn(II) Complexes as Conjugate Acid−Base Catalysts for Enantioselective Dialkylzinc Addition to Aldehydes
  作者：Manabu Hatano、Takashi Miyamoto、Kazuaki Ishihara

  DOI：10.1021/jo060908t

  日期：2006.8.1

  A highly enantioselective dialkylzinc (R22Zn) addition to a series of aromatic, aliphatic, and heteroaromatic aldehydes (5) was developed based on conjugate Lewis acid−Lewis base catalysis. Bifunctional BINOL ligands bearing phosphine oxides [P(O)R2] (7), phosphonates [P(O)(OR)2] (8 and 9), or phosphoramides [P(O)(NR2)2] (10) at the 3,3‘-positions were prepared by using a phospho-Fries rearrangement

  基于共轭路易斯酸-路易斯碱催化，开发了对一系列芳族，脂族和杂芳族醛（5）的高对映选择性二烷基锌（R 2 2 Zn）。带有氧化膦[P（O）R 2 ]（7），膦酸酯[P（O）（OR）2 ]（8和9）或磷酰胺[P（O）（NR 2）2 ]（10的双功能BINOL配体）通过使用磷酸化-弗里斯重排作为关键步骤来制备3,3'-位。NaphO-Zn（II）-R 2的配位中心以路易斯酸为底物上的羰基，并在3,3'-二磷酰基-BINOL-Zn（II）中以磷酰基（PO）为路易斯碱活化R 2 2 Zn（II）催化剂可以以高对映选择性（高达> 99％ee）促进碳-碳键的形成。通过X射线分析游离配体（7）和四核Zn（II）团簇（21）进行了机理研究，对Zn（II）配合物进行31 P NMR实验，在配体之间没有非线性效应（7））和苯甲醛的Et加合物，以及与某些手性或非手性Zn（II）配合物的化学计量反应，提出了一种包含单体活性中间体的过渡态组装体。
• Synthesis and Application of 3,3′-Diarylmethyl BINOLs
  作者：Qing-Hua Fan、Yi-Li Zhang、Feng Zhang、Wei-Jun Tang、Qing-Lai Wu

  DOI：10.1055/s-2006-932475

  日期：——

  A new class of 3,3′-diarylmethyl BINOL derivatives were synthesized and applied to the catalytic asymmetric addition of diethylzinc to aldehydes. These chiral diol auxiliaries could be used as catalysts without the addition of Ti(i-PrO)4 and showed unprecedented catalytic activities and enantioselectivities (up to 94% ee, 5 mol% catalyst loading).

  合成了一类新的3,3′-二芳基甲基BINOL衍生物，并将其应用于二乙基锌对醛的催化不对称加成反应。这些手性二醇辅助剂可以作为催化剂使用，而无需添加Ti(i-PrO)4，并表现出前所未有的催化活性和对映选择性（最高可达94%的对映体过量，催化剂负载量为5摩尔%）。
• A New Ligand Scaffold for Catalytic Asymmetric Alkylzinc Additions to Aldehydes
  作者：Peter Wipf、Xiaodong Wang

  DOI：10.1021/ol025600c

  日期：2002.4.1

  text] 1,3-Azole derivatives of 2-aminocyclohexanecarboxylic acid represent a new class of bidentate ligands for metal-mediated catalytic asymmetric synthesis. N-[2-(4-Isopropyl-4,5-dihydrooxazol-2-yl)cyclohexyl]methanesulfonamide (6) is particularly well suited for the addition of alkylzinc reagents to aliphatic aldehydes in high enantiomeric excess.

  [反应：见正文] 2-氨基环己烷羧酸的1,3-偶氮衍生物代表了金属介导的催化不对称合成的一类新的双齿配体。N- [2-（4-异丙基-4,5-二氢恶唑-2-基）环己基]甲磺酰胺（6）特别适合于以高对映体过量将烷基锌试剂添加到脂肪族醛中。
• A novel P450-based biocatalyst for the selective production of chiral 2-alkanols
  作者：Clemens J. von Bühler、Vlada B. Urlacher

  DOI：10.1039/c4cc00647j

  日期：——

  A P450 monooxygenase from Nocardia farcinica (CYP154A8) catalyses the stereo- and regioselective hydroxylation of n-alkanes, still a challenging task in chemical catalysis. In a biphasic reaction system, the regioselectivity for the C2-position of C7–C9 alkanes was over 90%. The enzyme showed strict S-selectivity for all tested substrates, with enantiomeric excess (ee) of up to 91%.

  来自诺卡氏菌的P450单氧化酶（CYP154A8）催化n-烷烃的立体选择性和区位选择性羟基化，这在化学催化中仍然是一项具有挑战性的任务。在双相反应系统中，C7–C9烷烃C2位的区位选择性超过90%。该酶对所有测试底物表现出严格的S选择性，伴随的对映体过量（ee）高达91%。
• Enantioselective addition of diethylzinc to aldehydes using 2-azanorbornylmethanols and 2-azanorbornylmethanethiol as a catalyst
  作者：Hiroto Nakano、Noriyuki Kumagai、Hisao Matsuzaki、Chizuko Kabuto、Hiroshi Hongo

  DOI：10.1016/s0957-4166(97)00118-3

  日期：1997.5

  2-azanorbornylmethanols and 2-azanorbornylmethanethiol were prepared from ethyl (1S,3S,4R)-2-[(R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate and catalyzed the enantioselective addition of diethylzinc to aldehydes to give optically active secondary alcohols.

  由乙基（1 S，3 S，4 R）-2-[（（R）-1-苯基乙基）-2-氮杂双环[2.2.1]庚-5-烯- 3-羧酸酯化并催化二乙基锌对醛的对映选择性加成，得到旋光性仲醇。