(S)-8-(benzyloxy)oct-1-en-4-ol | 740817-77-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-8-(benzyloxy)oct-1-en-4-ol
• 英文别名: (S)-8-benzyloxyoct-1-en-4-ol；(4S)-8-phenylmethoxyoct-1-en-4-ol
• CAS: 740817-77-0
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: DDLVVUGZZSFOCL-OAHLLOKOSA-N

物化性质

• 沸点：
  351.8±37.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-8-(benzyloxy)oct-1-en-4-ol 在 lithium aluminium tetrahydride 、 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 23.0h， 生成 tert-butyl (S)-2-propylpiperidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of optically active heterocyclic compounds via deracemization of 1,2-diol monotosylate derivatives bearing a long aliphatic chain by a combination of enzymatic hydrolysis with Mitsunobu inversion

  摘要：

  We have succeeded in accomplishing the deracemization of (+/-)-2-acetoxydecyl and (+/-)-acetoxy-6-benzyloxyhexyl tosylates, which have a long substituent, via an enzyme-mediated enantioselective hydrolysis with a Mitsunobu inversion using polymer-supported triphenylphosphine to afford the corresponding (S)-enantiomer. Enantiomerically pure (S)- and (R)-gamma-dodecalactones, a fruit flavor, were synthesized from (S)-2-acetoxydecyl tosylate as the mutual starting material. The poisonous alkaloid (S)-coniine was also synthesized using enantiomerically pure allyl amine as the key intermediate derived from (S)-acetoxy-6-benzyloxyhexyl tosylate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.023
• 作为产物：
  描述：

  6-benzyloxy-1-hexene 在 吡啶 、 四氧化锇 、 lipase PS from Burkholderia cepacia 、 水 、 二正丁基氧化锡 、 potassium carbonate 、 N-甲基吗啉氧化物 、 三乙胺 、 copper(I) bromide 作用下， 以 四氢呋喃 、 甲醇 、 aq. phosphate buffer 、 二氯甲烷 、 丙酮 为溶剂， 反应 49.0h， 生成 (S)-8-(benzyloxy)oct-1-en-4-ol
  参考文献：
  名称：

  Synthesis of optically active heterocyclic compounds via deracemization of 1,2-diol monotosylate derivatives bearing a long aliphatic chain by a combination of enzymatic hydrolysis with Mitsunobu inversion

  摘要：

  We have succeeded in accomplishing the deracemization of (+/-)-2-acetoxydecyl and (+/-)-acetoxy-6-benzyloxyhexyl tosylates, which have a long substituent, via an enzyme-mediated enantioselective hydrolysis with a Mitsunobu inversion using polymer-supported triphenylphosphine to afford the corresponding (S)-enantiomer. Enantiomerically pure (S)- and (R)-gamma-dodecalactones, a fruit flavor, were synthesized from (S)-2-acetoxydecyl tosylate as the mutual starting material. The poisonous alkaloid (S)-coniine was also synthesized using enantiomerically pure allyl amine as the key intermediate derived from (S)-acetoxy-6-benzyloxyhexyl tosylate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.023

文献信息

• Catalytic asymmetric allylations of achiral and chiral aldehydes via BINOL–Zr complex
  作者：Michio Kurosu、Miguel Lorca

  DOI：10.1016/s0040-4039(02)00139-9

  日期：2002.3

  The complex generated from BINOL, Zr(OtBu)4, and 4 Å MS in toluene–pivalonitrile is very effective for catalytic asymmetric allylation of aldehydes using allyltributyltin. The reactions of achiral aldehyde under these conditions are completed within 3 h using 10–20 mol% of the complex at −20°C. The ees of homoallylic alcohols can be enhanced up to 98% via the tandem asymmetric allylation–Oppenauer

  由甲苯，新戊腈中的BINOL，Zr（O t Bu）4和4ÅMS生成的络合物对于使用烯丙基三丁基锡催化醛的催化不对称烯丙基化非常有效。在20°C下，使用10–20 mol％的配合物，可在3小时内完成这些条件下的非手性醛的反应。通过串联不对称烯丙基化-Oppenauer氧化可将均丙醇的ee提高至98％。对β-烷氧基醛的这些条件的范围和局限性进行了广泛的研究。
• A highly enantioselective allyl-transfer through suppression of epimerization
  作者：Cheng-Hsia Angeline Lee、Teck-Peng Loh

  DOI：10.1016/j.tetlet.2004.06.014

  日期：2004.7

  A highly enantioselective allyl transfer method was successfully developed, producing terminal homoallylic alcohols in moderate to high yields. In all cases, reactions were carried out under mild acid conditions; reducing the reaction temperature suppressed racemization.

  成功开发出一种高对映选择性的烯丙基转移方法，可以中等至高收率生产末端均烯丙基醇。在所有情况下，反应均在弱酸条件下进行；降低反应温度可抑制外消旋作用。
• Olefin Metathesis−Iodoetherification−Dehydroiodination Strategy for Spiroketal Subunits of Polyether Antibiotics
  作者：Kurissery A. Tony、Darrin Dabideen、Jialiang Li、Maria Dolores Díaz-Hernández、Jesús Jiménez-Barbero、David R. Mootoo

  DOI：10.1021/jo9014722

  日期：2009.10.16

  The convergent synthesis of two pentacyclic analogues of the polyether monensin A is described. Although different with respect to the configuration of the alcohol at the 3 position of the six-membered ring of the spiroketal subunit, the configuration at the acetal center in both structures is unchanged and is consistent with the anomeric effect. The key synthetic steps are the coupling of two complex

  描述了聚醚莫能菌素 A 的两个五环类似物的聚合合成。尽管在螺缩醛亚基的六元环的 3 位上醇的构型不同，但两种结构中缩醛中心的构型没有变化，并且与异头效应一致。关键的合成步骤是通过烯烃复分解将两个复杂链段偶联，然后通过碘醚化-脱氢碘化序列将二羟基烯烃转化为螺缩酮。这些转换与各种功能组的兼容性使得整体策略适用于高度取代的框架。
• Facile Entry to Substituted Decahydroquinoline Alkaloids. Total Synthesis of Lepadins A−E and H
  作者：Xiaotao Pu、Dawei Ma

  DOI：10.1021/jo061070c

  日期：2006.8.1

  Condensation of a L-alanine derived delta-bromo-beta-silyloxy-propylamine with 1,3-cyclohexadione followed by alkylative cyclization produces a bicyclic enone. Diastereoselective Pt/C-catalyzed hydrogenation of this enone in HOAc provides a 5-oxo-cis-fused decahydroquinoline. Wittig olefination of this decahydroquinoline and subsequent epimerization of the resulting 5-formyl intermediate gives rise to a 5-beta-formyl decahydroquinoline exclusively. In a parallel procedure, Peterson reaction of this decahydroquinoline and subsequent hydrogenation of the generated 5-exo-olefin provides a decahydroquinoline with a 5-alpha-substituent predominantly. For these two diastereoselective processes, using the intermediates without N-protection as the substrates is essential because the corresponding N-Boc intermediates give poor diastereoselectivity. The intermediate with beta-form side chain is further converted into lepadins A-C via carbon chain elongation, while the intermediate with alpha-form side chain is transformed into lepadins D, E, and H and corresponding 5'-epimers via connection with two sulfones generated from two Sharpless epoxidation products. By comparison of the rotations and NMR data, the stereochemistry of lepadins D, E, and H is assigned as 2S, 3R, 4aS, 5S, 8aR, 5'R.
• Studies directed toward the synthesis of caylobolide A: convergent synthesis of C21–C40 subunit
  作者：J.S. Yadav、N. Swapnil、M. Venkatesh、A.R. Prasad

  DOI：10.1016/j.tetlet.2013.12.091

  日期：2014.2

  Stereoselective synthesis of the C21-C40 core segment of caylobolide A has been achieved following a highly efficient convergent strategy. The key reactions featured in the synthesis are Prins cyclization, reductive radical cyclization, Sharpless asymmetric epoxidation and olefin cross metathesis. (C) 2014 Published by Elsevier Ltd.