(2S,4R)-4-(Cyclohex-1-enyloxy)-pentan-2-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4R)-4-(Cyclohex-1-enyloxy)-pentan-2-ol
• 英文别名: (2S,4R)-4-(cyclohexen-1-yloxy)pentan-2-ol
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: QJJMGPBBUHGQSJ-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (2S,4R)-4-(Cyclohex-1-enyloxy)-pentan-2-ol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Diazo-acetic acid (1S,3R)-3-(cyclohex-1-enyloxy)-1-methyl-butyl ester
  参考文献：
  名称：

  与温度无关的立体控制 [2+2] 环加成。2,4-戊二醇系链在不对称反应中作为差异活化熵促进剂的潜力

  摘要：

  DOI：

  10.1021/ja993976o
• 作为产物：
  描述：

  (2R,4S)-2,4-pentanediol 在 吡啶 、 三异丁基铝 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 (2S,4R)-4-(Cyclohex-1-enyloxy)-pentan-2-ol
  参考文献：
  名称：

  与温度无关的立体控制 [2+2] 环加成。2,4-戊二醇系链在不对称反应中作为差异活化熵促进剂的潜力

  摘要：

  DOI：

  10.1021/ja993976o

文献信息

• Stereospecific annulation of hydroxy vinyl ethers. Synthetic application to polyfunctionalized cyclic compounds
  作者：Naoyuki Hanaki、Kazuaki Ishihara、Makoto Kaino、Yuji Naruse、Hisashi Yamamoto

  DOI：10.1016/0040-4020(96)00253-0

  日期：1996.5

  Stereospecific annulation of hydroxy vinyl ethers in the presence of triflic anhydride and tertiary amines and its synthetic application are described. Each 1-hydroxy-2-oxabicyclo[n.4.0]alkane, 2-oxabicyclo[n.4.0]alk-1(6)-ene and 2-oxabicyclo[n.4.0]alk-1(6+n)-ene is stereoselectively synthesized from the same hydroxy vinyl ether depending on the choice of the reaction conditions (temperature, solvent

  描述了在三氟甲磺酸酐和叔胺存在下的羟基乙烯基醚的立体定向环氧化及其合成应用。每个1-羟基-2-氧杂双环[n.4.0]烷烃，2-氧杂双环[n.4.0] alk-1（6）-烯和2-氧杂双环[n.4.0] alk-1（6 + n）-烯根据反应条件（温度，溶剂和叔胺）的选择，由相同的羟基乙烯基醚立体选择性地合成。这些化合物导致多官能化的环状化合物和一些天然产物。我们提出，这种环化反应是通过纯S N 2样机理进行的。
• Highly regio- and stereo-selective annulation–elimination reactions of 1-cycloalkenyl 3-hydroxypropyl ethers
  作者：Kazuaki Ishihara、Naoyuki Hanaki、Hisashi Yamamoto

  DOI：10.1039/c39950001117

  日期：——

  Highly regio- and stereo-selective annulation–elimination reactions of 1-cycloalkenyl 3-hydroxypropyl ethers in the presence of triflic anhydride and tertiary amines are described; the bicyclic vinyl ethers produced are converted to 2-substituted δ-lactones, macrocyclic oxolactones and bicyclic hydroxy ethers by ozonolysis and stereoselective hydroboration.

  描述了在三酸酐和叔胺存在下，1-环烯基 3-羟基丙基醚的高区域和立体选择性环化羰基化反应；生成的双环乙烯基醚通过臭氧分解和立体选择性氢硼化合反应转化为 2-取代的δ-内酯、大环氧内酯和双环羟基醚。
• Stereochemical study on an oxygen-directed olefin oxidation and subsequent oxygen cyclization: Differences between peracid and metal oxide-catalyzed hydroperoxide in oxidation reactions
  作者：Aya Inoue、Tomonori Misaki、Morifumi Fujita、Tadashi Okuyama、Takashi Sugimura

  DOI：10.1016/j.tetasy.2013.05.025

  日期：2013.7

  Optically active (2S,4R)-2-hydroxy-4-pentyl enol ether was prepared for the first time and subjected to hydroxy-directed oxidations at the olefinic group. Treatment with m-chloroperbenzoic acid and tertbutyl hydroperoxide/vanadium acetylacetonate resulted in the same stereoface differentiation at the olefin, with diastereomeric excesses as high as 79% and 92%, respectively, whereas the stereochemistry of the products of subsequent nucleophilic additions of the hydroxy group was opposite. (C) 2013 Elsevier Ltd. All rights reserved.
• Temperature-Independent Stereocontrolled [2+2] Cycloaddition. Potential of the 2,4-Pentanediol Tether in Asymmetric Reactions as a Differential Activation Entropy Promoter
  作者：Takashi Sugimura、Takahiro Tei、Atsushi Mori、Tadashi Okuyama、Akira Tai

  DOI：10.1021/ja993976o

  日期：2000.3.1