(E)-(R)-Hex-4-ene-1,2-diol | 143289-05-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-(R)-Hex-4-ene-1,2-diol
• 英文别名: (E,2R)-hex-4-ene-1,2-diol
• CAS: 143289-05-8
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: DBRGGEXIRVNLPF-YRFDSLTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  8
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-(R)-Hex-4-ene-1,2-diol 在 盐酸 、 4-二甲氨基吡啶 、 lithium 、 sodium hydride 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氨 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 28.03h， 生成 (+)-prelactone C
  参考文献：
  名称：

  A convergent route to β-hydroxy δ-lactones through Prins cyclisation as the key step: synthesis of (+)-prelactones B, C and V

  摘要：

  Reactions of homoallylic alcohols with aldehydes in the presence of acid catalysts gave multisubstituted tetrahydropyrans with the creation of one to three new stereogenic centres in a single-pot process. The utility of this approach is extended to the enantioselective syntheses of (+)-prelactones B, C and V. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.121
• 作为产物：
  描述：

  (R)-1-benzyloxy-4-hexyne-2-ol 在 氨 、 sodium 作用下， 以84%的产率得到(E)-(R)-Hex-4-ene-1,2-diol
  参考文献：
  名称：

  Practical chiral route to muscarine and its three diastereomers.

  摘要：

  从易于获得的手性起始材料开始，已经开发出一种制备光学纯形式的毒蕈碱生物碱的所有可能立体异构体的实用途径。

  DOI：

  10.1248/cpb.43.1067

文献信息

• An Efficient Stereoselective Synthesis of Key Fragments of Elaiophylin
  作者：Pannala Padmaja、Pedavenkatagari Narayana Reddy、Jhillu Singh Yadav

  DOI：10.1002/hlca.201600006

  日期：2016.7

  The stereoselective synthesis of key fragments 3 and 7 of elaiophylin has been accomplished from readily available epichlorohydrin as the starting material. The key reactions involved are Jacobsen's kinetic resolution, Prins cyclization, pyridinium chlorochromate‐mediated oxidative cleavage, Grignard reaction, and cross‐metathesis reaction.

  弹性蛋白的关键片段3和7的立体选择性合成已经从容易获得的表氯醇作为起始原料完成。涉及的关键反应是Jacobsen的动力学拆分，Prins环化，氯铬酸吡啶鎓介导的氧化裂解，Grignard反应和交叉复分解反应。
• Practical chiral route to muscarine and its three diastereomers.
  作者：Yukio OHSHIBA、Takehiko YOSHIMITSU、Kunio OGASAWARA

  DOI：10.1248/cpb.43.1067

  日期：——

  A practical route to all possible stereoisomers of the muscarine alkaloids in optically pure forms has been developed starting from a readily accessible chiral starting material.

  从易于获得的手性起始材料开始，已经开发出一种制备光学纯形式的毒蕈碱生物碱的所有可能立体异构体的实用途径。
• Stereoselective synthesis of basiliskamides A and B via Prins cyclisation
  作者：J.S. Yadav、P. Purushothama Rao、M. Sridhar Reddy、A.R. Prasad

  DOI：10.1016/j.tetlet.2008.07.024

  日期：2008.9

  A stereoselective and convergent approach to basiliskamides A and B is achieved through our recently developed strategy for the construction of polyketide precursors via Prins cyclisation. The approach mainly relies upon reductive opening of 1-iodomethyl cyclic ethers, Mitsunobu inversion, Takai olefination and Stille coupling along with Prins cyclisation. (c) 2008 Elsevier Ltd. All Fights reserved.
• A convergent route to β-hydroxy δ-lactones through Prins cyclisation as the key step: synthesis of (+)-prelactones B, C and V
  作者：J.S. Yadav、M. Sridhar Reddy、A.R. Prasad

  DOI：10.1016/j.tetlet.2005.01.121

  日期：2005.3

  Reactions of homoallylic alcohols with aldehydes in the presence of acid catalysts gave multisubstituted tetrahydropyrans with the creation of one to three new stereogenic centres in a single-pot process. The utility of this approach is extended to the enantioselective syntheses of (+)-prelactones B, C and V. (C) 2005 Elsevier Ltd. All rights reserved.