(R)-1-(4-Methoxy-benzyloxy)-hex-5-en-2-ol | 1012367-43-9

• 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: (R)-1-(4-Methoxy-benzyloxy)-hex-5-en-2-ol
• 英文别名: (2R)-1-[(4-methoxyphenyl)methoxy]hex-5-en-2-ol
• CAS: 1012367-43-9
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: ZIYLAWYMIQFWLX-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-(4-Methoxy-benzyloxy)-hex-5-en-2-ol 在 sodium hydride 、 二甲基亚砜 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 paraffin oil 为溶剂， 反应 12.25h， 生成 (1S)-1-[(4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]butyl (2R)-2-(benzyloxy)-5-hexenoate
  参考文献：
  名称：

  Titanium(IV)-Promoted Regioselective Nucleophilic Ring-Opening Reaction of Chiral Epoxyallyl Alcohols with Acids as a Tool for Ready Access to Chiral 1,2,3-Triol Monoesters: Application to Stereoselective Total Synthesis of Macrolides

  摘要：

  Titanium(IV)-promoted regioselective ring-opening reaction of chiral epoxy-allyl alcohols (Sharpless conditions as the key strategic step) is developed as a tool for ready access to chiral 5,6-dihydroxyoct-7-en-4-yl alkoxylates. Later, the synthetic utility of products thereof was demonstrated through the RCM based stereoselective synthesis of various natural products.

  DOI：

  10.1021/jo202199g
• 作为产物：
  描述：

  (R)-2-(((4-methoxybenzyl)oxy)methyl)oxirane 、 3-氯丙烯 在 magnesium 作用下， 以 乙醚 为溶剂， 以90%的产率得到(R)-1-(4-Methoxy-benzyloxy)-hex-5-en-2-ol
  参考文献：
  名称：

  一种立体选择性方法全合成Clonostachydiol

  摘要：

  使用容易获得的 (±)-表氯醇作为前体，完成了氯硝醇的立体选择性合成。该合成涉及直接和直接的反应，例如 Sharpless 不对称环氧化、碘化、环氧化物与烯丙基氯化镁的立体选择性打开和 Sharpless 不对称二羟基化。

  DOI：

  10.1055/s-0028-1087296

文献信息

• Total Synthesis of Dinophysistoxin-2 and 2-epi-Dinophysistoxin-2 and Their PPase Inhibition
  作者：Yucheng Pang、Chao Fang、Michael J. Twiner、Christopher O. Miles、Craig J. Forsyth

  DOI：10.1002/anie.201101741

  日期：2011.8.8

  The first total syntheses of the title compounds highlight novel assemblies of the C1–C14 and C28–C38 domains, including an unexpected diastereoselectivity in the Sharpless asymmetric dihydroxylation of an alkene at C1C2. PPase inhibition assays revealed that 2‐epi‐DTX‐2 is at least 1 to 2 orders of magnitude less potent than DTX‐2, thus indicating that the configuration at C2 in DTX‐2 is crucial

  标题化合物的第一个总合成突显了C1-C14和C28-C38结构域的新颖组装，包括在C1C2处烯烃的Sharpless不对称二羟基化反应中出乎意料的非对映选择性。PPase抑制试验表明，2 - epi -DTX-2的效力比DTX-2至少低1至2个数量级，因此表明DTX-2中C2的构型对于有效抑制至关重要（见图）。
• Synthesis of the DE-ring of goniodomin A and prediction of its natural relative stereochemistry
  作者：Takahiro Katagiri、Kenshu Fujiwara、Hidetoshi Kawai、Takanori Suzuki

  DOI：10.1016/j.tetlet.2007.11.084

  日期：2008.1

  stereochemically unidentified antifungal agent in 1987 by Murakami. In this study, two stereoisomeric series of non-macrocyclic and macrocyclic DE-ring model compounds of 1 were synthesized, and the natural relative stereochemistry of the DE-ring was predicted by NMR comparison of 1 with these model compounds.

  村上隆于1987年首次从平叶亚历山大藻中分离了Goniodomin A（1），作为一种立体化学未鉴定的抗真菌剂。在这项研究中，合成了两个非大环和大环DE-环模型化合物1的立体异构体系列，并通过NMR比较1与这些模型化合物预测了DE-环的自然相对立体化学。
• Stereodivergent Construction of Cyclic Ethers by a Regioselective and Enantiospecific Rhodium-Catalyzed Allylic Etherification: Total Synthesis of Gaur Acid
  作者：P. Andrew Evans、David K. Leahy、William J. Andrews、Daisuke Uraguchi

  DOI：10.1002/anie.200460612

  日期：2004.9.13
• Titanium(IV)-Promoted Regioselective Nucleophilic Ring-Opening Reaction of Chiral Epoxyallyl Alcohols with Acids as a Tool for Ready Access to Chiral 1,2,3-Triol Monoesters: Application to Stereoselective Total Synthesis of Macrolides
  作者：Palakodety Radha Krishna、D. Venkata Ramana

  DOI：10.1021/jo202199g

  日期：2012.1.6

  Titanium(IV)-promoted regioselective ring-opening reaction of chiral epoxy-allyl alcohols (Sharpless conditions as the key strategic step) is developed as a tool for ready access to chiral 5,6-dihydroxyoct-7-en-4-yl alkoxylates. Later, the synthetic utility of products thereof was demonstrated through the RCM based stereoselective synthesis of various natural products.
• A Stereoselective Approach for the Total Synthesis of Clonostachydiol
  作者：J. Yadav、T. Swamy、B. Reddy

  DOI：10.1055/s-0028-1087296

  日期：——

  A stereoselective synthesis of clonostachydiol is accomplished using readily available (±)-epichlorohydrin as a precursor. The synthesis involves direct and straightforward reactions such as Sharpless asymmetric epoxidation, iodination, stereoselective opening of epoxide with allylmagnesium chloride and Sharpless asymmetric dihydroxylation.

  使用容易获得的 (±)-表氯醇作为前体，完成了氯硝醇的立体选择性合成。该合成涉及直接和直接的反应，例如 Sharpless 不对称环氧化、碘化、环氧化物与烯丙基氯化镁的立体选择性打开和 Sharpless 不对称二羟基化。