(2R)-(E)-4-Hepten-2-ol

• 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: (2R)-(E)-4-Hepten-2-ol
• 英文别名: (R,E)-hept-4-en-2-ol；(2R)-hept-4-en-2-ol；(E,2R)-hept-4-en-2-ol
• 化学式: C₇H₁₄O
• 分子量: 114.188
• InChiKey: KZUFTCBJDQXWOJ-SMMXGFFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (2R)-(E)-4-Hepten-2-ol 在 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.08h， 生成 (R,E)-6-(propa-1,2-dienyloxy)hept-3-ene
  参考文献：
  名称：

  钌催化的二氢吡喃乙缩醛的区域选择性烯烃迁移：从头开始向β-2,6-Dideoxypyranoglycosides的策略。

  摘要：

  在这里，我们报道了针对β-2,6-dideoxypyranoglycosides的从头合成策略。关键事件是二氢吡喃烯丙基乙缩醛向均烯丙基缩醛的钌催化的区域选择性烯烃迁移。结合其他金属催化的反应，该新方案导致以高效方式合成β-2,6-二脱氧吡喃葡萄糖苷。使用这种顺序的金属催化，制备了β-2，6-二脱氧吡喃葡萄糖苷的各种单糖，二糖和三糖形式。

  DOI：

  10.1021/acs.orglett.0c00279
• 作为产物：
  描述：

  (R)-pent-4-yn-2-ol 在 咪唑 、 lithium amide 、 氢氟酸 、 氨 、 sodium 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成 (2R)-(E)-4-Hepten-2-ol
  参考文献：
  名称：

  Identification of a novel moth sex pheromone inEriocrania cicatricella (Zett.) (Lepidoptera: Eriocraniidae) and its phylogenetic implications

  摘要：

  Extracts from different body parts of adult female Eriocrania cicatricella (Zett.) were tested for electrophysiological activity on conspecific male antennae. Extracts from the Vth abdominal segment, containing a pair of exocrine glands, elicited the largest electroantennographic response when compared to extracts of other body parts. Female extracts were analyzed by gas chromatography with simultaneous flame ionization and electroantennographic detection (EAD). The EAD active peaks were identified as (Z)-4-hepten-2-one, (2R)-heptane-2-ol, and (2R)-(Z)-4-hepten-2-ol by coinjection on a gas chromatography and by comparison of mass spectra with those of synthetic standards. In field tests, a blend of these three pheromone components was highly attractive to conspecific males, and a subtractive assay confirmed that the unsaturated alcohol is the major pheromone component, whereas no definite behavioral activity could be assigned to the ketone or the saturated alcohol. A bait containing the two alcohols with S-configuration was attractive to male E. sparrmannella (Bosc), whereas no males of E. cicatricella were found in these traps. The sex pheromone compounds in E. cicatricella are chemically similar to pheromones reported in Trichoptera and they are produced in homologous glands.

  DOI：

  10.1007/bf02033660

文献信息

• Ruthenium-Catalyzed Regioselective Olefin Migration of Dihydropyran Acetals: A <i>De Novo</i> Strategy toward β-2,6-Dideoxypyranoglycosides
  作者：Kyeongdeok Seo、Young Ho Rhee

  DOI：10.1021/acs.orglett.0c00279

  日期：2020.3.20

  toward β-2,6-dideoxypyranoglycosides. The key event is the ruthenium-catalyzed regioselective olefin migration of dihydropyran allylic acetals to homoallylic acetals. In combination with other metal-catalyzed reactions, this new protocol led to the synthesis of β-2,6-dideoxypyranoglycosides in a highly efficient manner. Using this sequential metal catalysis, various mono-, di-, and trisaccharide forms

  在这里，我们报道了针对β-2,6-dideoxypyranoglycosides的从头合成策略。关键事件是二氢吡喃烯丙基乙缩醛向均烯丙基缩醛的钌催化的区域选择性烯烃迁移。结合其他金属催化的反应，该新方案导致以高效方式合成β-2,6-二脱氧吡喃葡萄糖苷。使用这种顺序的金属催化，制备了β-2，6-二脱氧吡喃葡萄糖苷的各种单糖，二糖和三糖形式。
• Identification of a novel moth sex pheromone inEriocrania cicatricella (Zett.) (Lepidoptera: Eriocraniidae) and its phylogenetic implications
  作者：Junwei Zhu、Mikhail V. Kozlov、Peter Philipp、Wittko Francke、Christer Löfstedt

  DOI：10.1007/bf02033660

  日期：1995.1

  Extracts from different body parts of adult female Eriocrania cicatricella (Zett.) were tested for electrophysiological activity on conspecific male antennae. Extracts from the Vth abdominal segment, containing a pair of exocrine glands, elicited the largest electroantennographic response when compared to extracts of other body parts. Female extracts were analyzed by gas chromatography with simultaneous flame ionization and electroantennographic detection (EAD). The EAD active peaks were identified as (Z)-4-hepten-2-one, (2R)-heptane-2-ol, and (2R)-(Z)-4-hepten-2-ol by coinjection on a gas chromatography and by comparison of mass spectra with those of synthetic standards. In field tests, a blend of these three pheromone components was highly attractive to conspecific males, and a subtractive assay confirmed that the unsaturated alcohol is the major pheromone component, whereas no definite behavioral activity could be assigned to the ketone or the saturated alcohol. A bait containing the two alcohols with S-configuration was attractive to male E. sparrmannella (Bosc), whereas no males of E. cicatricella were found in these traps. The sex pheromone compounds in E. cicatricella are chemically similar to pheromones reported in Trichoptera and they are produced in homologous glands.