(S)-(E)-1,5-Heptadien-4-ol | 81076-05-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(E)-1,5-Heptadien-4-ol
• 英文别名: (4S,5E)-(+)-hepta-1,5-dien-4-ol；(S,E)-(+)-hepta-1,5-dien-4-ol；(4S,5E)-hepta-1,5-dien-4-ol
• CAS: 81076-05-3
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: SIYWFIPUQCEZII-KNIZRNDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-(E)-1,5-Heptadien-4-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 硫酸 、 (+)-Weinsaeure-diethylester 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 生成 (2R,3R,4S)-Hept-6-ene-2,3,4-triol
  参考文献：
  名称：

  Total synthesis of carbohydrates: stereoselective syntheses of 2,6-dideoxy-D-arabino-hexose and 2,6-dideoxy-D-ribo-hexose

  摘要：

  DOI：

  10.1021/jo00346a050
• 作为产物：
  描述：

  (5E)-hepta-1,5-dien-4-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 (-)-diisopropyl tartrate 作用下， 以 二氯甲烷 为溶剂， 以27%的产率得到(4R,5R,6R)-5,6-epoxyhept-1-en-4-ol
  参考文献：
  名称：

  Total synthesis of carbohydrates: stereoselective syntheses of 2,6-dideoxy-D-arabino-hexose and 2,6-dideoxy-D-ribo-hexose

  摘要：

  DOI：

  10.1021/jo00346a050

文献信息

• Lewis Base Catalyzed Enantioselective Allylation of α,β-Unsaturated Aldehydes
  作者：Aneta Kadlčíková、Irena Valterová、Lucie Ducháčková、Jana Roithová、Martin Kotora

  DOI：10.1002/chem.201001523

  日期：2010.8.16

  Being selective: The catalytic allylation of α,β‐unsaturated aldehydes with allyltrichlorosilane in the presence of chiral 3,3′‐unsymmetrically substituted bis(tetrahydroisoquinoline) N,N‐dioxides was explored. The allylation of various aldehydes proceeded under mild reaction conditions (−78 °C) with high yields and enantioselectivity (see scheme). This allylation was applied in the synthesis of (

  具有选择性：探索了在手性3,3'-不对称取代的双（四氢异喹啉）N，N-二氧化物存在下，α，β-不饱和醛与烯丙基三氯硅烷的催化烯丙基化反应。各种醛的烯丙基化反应在温和的反应条件下（-78°C）以高收率和对映选择性进行（参见方案）。该烯丙基化被用于（S）-（-）-goniothalamin的合成。
• Tetrahydroisoquinoline-Based N-Oxides as Chiral Organocatalysts for the Asymmetric Allylation of Aldehydes
  作者：Tricia Naicker、Per I. Arvidsson、Hendrik G. Kruger、Glenn E. M. Maguire、Thavendran Govender

  DOI：10.1002/ejoc.201100923

  日期：2011.12

  The short synthesis of a series of novel chiral N-oxideorganocatalysts and their evaluation in the asymmetric allylation reaction of aromatic and α-β-unsaturated aldehydes with allyltrichlorosilane is reported. These readily modifiable organocatalysts are the first of their kind based on the tetrahydroisoquinoline framework. The chiral homoallyl products were obtained with good chemical efficiency

  报道了一系列新型手性 N-氧化物有机催化剂的短合成及其在芳烃和 α-β-不饱和醛与烯丙基三氯硅烷的不对称烯丙基化反应中的评价。这些易于改性的有机催化剂是基于四氢异喹啉骨架的同类有机催化剂中的第一个。在温和的反应条件 (23 °C) 下，以良好的化学效率（高达 93% 的产率）和高对映选择性（高达 91% ee）获得了手性高烯丙基产物。
• Oxyanion Orientation in Anionic Oxy-Cope Rearrangements
  作者：Eun Lee、Yong Rok Lee、Bongjin Moon、Ohyun Kwon、Mi Seong Shim、Jae Sook Yun

  DOI：10.1021/jo00085a037

  日期：1994.3

  Efficiency of chirality transfer in anionic oxy-Cope rearrangement depends solely on the orientational preference of the oxyanionic bond in the substrates with a single carbinol carbon chiral center. In chairlike transition-state conformations for the rearrangement of simplest substrates like anions generated from (E)-1-phenyl-1,5-hexadien-3-ol and (E)-1,5-heptadien-4-ol, the oxyanionic bond is more prone to adopt the pseudoaxial orientation. On the other hand, anions generated from (E)-2-methyl-1,5-heptadien-4-ol, (E)-5-tert-butyl-1-phenyl-1,5-hexadien-3-ol, and 4-(2'-methyl-1'-cyclohexenyl)-1-buten-3-ol undergo rearrangement via chairlike transition states in which the pseudoequatorial oxyanionic bond is favored. It can thus be surmized that there is a slight stereoelectronic preference for the pseudoaxial oxyanionic bond in the chairlike transition states for the rearrangement of substrates without steric constraints. Substitution at C5 of the basic 1,5-hexadien-3-ol framework of substrates, however, leads to 1,3-diaxial steric interaction in the chairlike transition states with pseudoaxial oxyanionic bond, and pseudoequatorial disposition of oxyanionic bond becomes more favorable.
• Lee Eun, Lee Yong Rok, Moon Bongjin, Kwon Ohyun, Shim Mi Seong, Yun Jae S+, J. Org. Chem, 59 (1994) N 6, S 1444-1456
  作者：Lee Eun, Lee Yong Rok, Moon Bongjin, Kwon Ohyun, Shim Mi Seong, Yun Jae S+

  DOI：——

  日期：——
• Total synthesis of carbohydrates: stereoselective syntheses of 2,6-dideoxy-D-arabino-hexose and 2,6-dideoxy-D-ribo-hexose
  作者：William R. Roush、Richard J. Brown

  DOI：10.1021/jo00346a050

  日期：1982.3