(3R,4R)-4-benzyloxy-hexa-1,5-dien-3-ol | 112790-78-0

• 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: (3R,4R)-4-benzyloxy-hexa-1,5-dien-3-ol
• 英文别名: (4R)-benzyloxyhexa-1,5-dien-(3R)-ol；(3R,4R)-4-(Benzyloxy)-1,5-hexadiene-3-ol；(3R,4R)-4-phenylmethoxyhexa-1,5-dien-3-ol
• CAS: 112790-78-0
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: DECMJLVAHLVDEM-CHWSQXEVSA-N

物化性质

• 沸点：
  312.3±30.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  (3R,4R)-4-benzyloxy-hexa-1,5-dien-3-ol 在 丙酸 9-borabicyclo[3.3.1]nonane dimer 作用下， 生成 (E)-(R)-6-Benzyloxy-8-hydroxy-oct-4-enoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of (3R,4R)-1,5-hexadien-3,4-diol and its unsymmetricalderivatives: Application to (R)-(+)-∝-lipoic acid

  摘要：

  DOI：

  10.1016/s0040-4039(00)96076-3
• 作为产物：
  描述：

  Acetic acid (1S,2S,3R)-2-benzyloxy-1-((R)-1,2-bis-methanesulfonyloxy-ethyl)-3,4-bis-methanesulfonyloxy-butyl ester 在 sodium methylate 、 sodium iodide 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (3R,4R)-4-benzyloxy-hexa-1,5-dien-3-ol
  参考文献：
  名称：

  Synthesis of (3R,4R)-1,5-hexadien-3,4-diol and its unsymmetricalderivatives: Application to (R)-(+)-∝-lipoic acid

  摘要：

  DOI：

  10.1016/s0040-4039(00)96076-3

文献信息

• Palladium-CatalyzedO-Allylation of α-Hydroxy Carbonyl Compounds
  作者：Bernd Schmidt、Stefan Nave

  DOI：10.1002/adsc.200505361

  日期：2006.3

  α-Hydroxy carbonyl compounds undergo smooth O-allylation using allylic carbonates and Pd(0) catalysts. This method has significant advantages over other O-allylation methods as it provides a solution to several problems previously observed for this synthetic transformation.

  α-羟基羰基化合物使用碳酸烯丙酯和Pd（0）催化剂进行平滑的O-烯丙基化。与其他O-烯丙基化方法相比，该方法具有显着优势，因为它提供了以前针对此合成转化观察到的几个问题的解决方案。
• Synthesis of Dihydrofurans and Dihydropyrans with Unsaturated Side Chains Based on Ring Size-Selective Ring-Closing Metathesis
  作者：Bernd Schmidt、Stefan Nave

  DOI：10.1002/adsc.200600473

  日期：2007.1.8

  Enantiomerically pure 1,5-hexadiene-3,4-diol, derived from D-mannitol in a few steps, may serve as a starting material for enantiopure dihydropyrans and dihydrofurans bearing an unsaturated side chain which is amenable for further synthetic transformations. The synthesis relies on a ring size-selective ring-closing metathesis reaction of a triene. Most likely, a catalyst-directing effect of an allylic

  在几个步骤中衍生自D-甘露醇的对映体纯的1,5-己二烯-3,4-二醇可作为对映体纯的二氢吡喃和带有不饱和侧链的二氢呋喃的原料，所述不饱和侧链适合于进一步的合成转化。合成依赖于三烯的环尺寸选择的闭环复分解反应。最可能的是，烯丙基羟基的催化剂导向作用是选择性的原因。
• Desymmetrization of (<i>R</i>,<i>R</i>)-Hexa-1,5-diene-3,4-diol via Monofunctionalization and Rhodium-Catalyzed Allylic Substitution
  作者：Bernd Schmidt、Lucia Staude

  DOI：10.1021/jo2001337

  日期：2011.4.1

  A sequence of selective monoprotection and Rh-catalyzed enantioconservative allylic substitution is established as a desymmetrization strategy for C2-symmetric hexa-1,5-diene-3,4-diol. A benzyl protecting group and ethyl carbonate as a leaving group emerged as the most useful combination with respect to reproducibility, stereoselectivity, and yield. A remarkable deviation from the normally observed

  建立了选择性单保护和Rh催化的对映保守性烯丙基取代的序列，作为C 2对称的hexa-1,5-diene-3,4-diol的去对称化策略。就可再现性，立体选择性和产率而言，苄基保护基和作为离去基团的碳酸乙酯是最有用的组合。对于未保护的碳酸盐，观察到与通常观察到的Rh催化的烯丙基烷基化的区域特异性显着偏离。在这种情况下，仅获得线性而不是支链的烷基化产物。
• Bidirectional Synthesis of 6-Acetoxy-5-hexadecanolide, the Mosquito Oviposition Pheromone of <i>Culex quinquefasciatus</i>, from a <i>C</i>₂-Symmetric Building Block Using Olefin Metathesis Reactions
  作者：Bernd Schmidt、Monib H. Petersen、Diana Braun

  DOI：10.1021/acs.joc.7b02944

  日期：2018.2.2

  syntheses of MOP starting from mannitol-derived (3R,4R)-hexa-1,5-diene-3,4-diol. This C2-symmetric building block is elaborated through bidirectional olefin metathesis reactions into 6-epi-MOP, which was converted into MOP via Mitsunobu inversion. The shortest of the three routes makes use of two sequential cross-metathesis reactions and an assisted tandem catalytic olefin reduction, induced by an in

  （5 R，6 S）-6-乙酰氧基-5-十六烷化物（MOP）是蚊子Cx的产卵信息素。quinquefasciatus，一种引起多种热带疾病的病原体。我们在此描述和评估了从甘露醇衍生的（3 R，4 R）-六-1,5-二烯-3,4-二醇开始的MOP的三种合成。该C 2对称结构单元是通过双向烯烃复分解反应制成6-表位的-MOP，通过Mitsunobu反演将其转换为MOP。这三种途径中最短的途径是利用两个顺序的交叉复分解反应和辅助的串联催化烯烃还原反应，这是由Ru-卡宾就地转化为Ru-氢化物引起的。
• Concise Total Synthesis of (−)-Muricatacin by Tandem Ring-Closing/Cross Metathesis
  作者：Kevin J. Quinn、André K. Isaacs、Rebecca A. Arvary

  DOI：10.1021/ol040047f

  日期：2004.11.1

  A strategy for the synthesis of chiral 5-(1-hydroxyalk-2-enyl)-5H-furan-2-ones and its application to the total synthesis of (-)-muricatacin, in four steps and 37% overall yield from (R,R)-hexa-1,5-diene-3,4-diol, are described. The key synthetic step in this approach is a highly regioselective and stereoselective tandem ring-closing/cross metathesis reaction in which both lactone formation and alkyl

  合成手性5-（1-羟基烷-2-烯基）-5H-呋喃-2-酮的策略及其在（-）-毛里卡他星全合成中的应用，分四个步骤进行，从（描述了R，R）-六-1,5-二烯-3,4-二醇。该方法中关键的合成步骤是高度区域选择性和立体选择性串联闭环/交叉复分解反应，其中内酯的形成和烷基链的延伸均通过有效的一锅法完成。