cyclooct-3-ene-trans-1,2-diol | 21491-46-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclooct-3-ene-trans-1,2-diol
• 英文别名: rel-(1R,2R,3Z)-cyclooct-3-en-1,2-diol；(1R,2R,3Z)-cyclooct-3-ene-1,2-diol
• CAS: 21491-46-3
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: AIWBBAVNOGRJMH-IZOSAOGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  cyclooct-3-ene-trans-1,2-diol 在 苯甲酸甲酯 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 14.0h， 生成 rel-(1S,2S,3E,pS)-cyclooct-3-en-1,2-diol 、 rel-(1S,2S,3E,pS)-cyclooct-3-en-1,2-diol
  参考文献：
  名称：

  A Photochemical Synthesis of Functionalized trans-Cyclooctenes Driven by Metal Complexation

  摘要：

  Described is a scalable procedure for driving photochemical sytheses of trans-cyclooctene derivatives through metal complexation. During photoirradiation, reaction mixtures are continuously pumped through a column of a AgNO(3)-impregnated silica gel. The trans-cyclooctene derivative is selectively retained by the AgNO3-impregnated silica, but the cis-isomer elutes from the column back to the reaction flask, where it is photoisomerized and recirculated through the column. The method provides access to a range of usefully functionalized derivatives of trans-cyclooctene, including a derivative of 5-aza-trans-cyclooctene that underwent transannular cyclization upon treatment with bromine. The alkene stereochemistry is transferred with high fidelity to the hexahydropyrrolizine framework in the transannular cyclization.

  DOI：

  10.1021/ja8001919
• 作为产物：
  描述：

  (3aS,4Z,9aS)-3a,6,7,8,9,9a-hexahydrocycloocta[d][1,3]dioxol-2-one 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以90%的产率得到cyclooct-3-ene-trans-1,2-diol
  参考文献：
  名称：

  A Photochemical Synthesis of Functionalized trans-Cyclooctenes Driven by Metal Complexation

  摘要：

  Described is a scalable procedure for driving photochemical sytheses of trans-cyclooctene derivatives through metal complexation. During photoirradiation, reaction mixtures are continuously pumped through a column of a AgNO(3)-impregnated silica gel. The trans-cyclooctene derivative is selectively retained by the AgNO3-impregnated silica, but the cis-isomer elutes from the column back to the reaction flask, where it is photoisomerized and recirculated through the column. The method provides access to a range of usefully functionalized derivatives of trans-cyclooctene, including a derivative of 5-aza-trans-cyclooctene that underwent transannular cyclization upon treatment with bromine. The alkene stereochemistry is transferred with high fidelity to the hexahydropyrrolizine framework in the transannular cyclization.

  DOI：

  10.1021/ja8001919

文献信息

• Direct epoxy alcohol synthesis from cyclic olefins using molecular oxygen and VO(acac)2-AIBN catalyst system
  作者：Kiyotomi Kaneda、Koichiro Jitsukawa、Takashi Itoh、Shiichiro Teranishi

  DOI：10.1021/jo01303a018

  日期：1980.7
• Vinyl epoxide hydrolysis reactions
  作者：Angela M. Ross、Terese M. Pohl、Kathryn Piazza、Michael Thomas、Bonnie Fox、Dale L. Whalen

  DOI：10.1021/ja00370a035

  日期：1982.3
• KANEDA KIYOTOMI; JITSUKAWA KOICHIRO; ITOH TAKASHI; TERANISHI SHIICHIRO, J. ORG. CHEM., 1980, 45, NO 15, 3004-3009
  作者：KANEDA KIYOTOMI、 JITSUKAWA KOICHIRO、 ITOH TAKASHI、 TERANISHI SHIICHIRO

  DOI：——

  日期：——