9-Oxabicyclo<4.2.1>non-7-en-1-ol | 37996-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 9-Oxabicyclo<4.2.1>non-7-en-1-ol
• 英文别名: 9-oxabicyclo[4.2.1]non-7-en-1-ol；1-Hydroxy-9-oxabicyclo<4.2.1>non-7-en；9-Oxa-bicylo<4.2.1>nonen-(2)-ol-(4)
• CAS: 37996-45-5
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: VLZDYGDTNNCQSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  9-Oxabicyclo<4.2.1>non-7-en-1-ol 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 26.0h， 以97%的产率得到(±)-(1R,6S,7S,9S)-8,10-dioxatricyclo[4.3.1.07,9]decane-1-ol
  参考文献：
  名称：

  Efficient and shortcut syntheses of some novel eight-membered ring cyclitols starting from cycloocta-1,3-diene

  摘要：

  Cyclooctane-1,2,3,4-tetraols, aminocyclooctanetriol, and chlorocyclooctanetriol were synthesized starting from cis,cis-1,3-cyclooctadiene by a concise and efficient method. Cyclooctene endoperoxide and cyclooctene epoxide obtained by photooxygenation and epoxidation, respectively, of cis,cis-1,3-cyclooctadiene were used as the key intermediates. The other oxygen, nitrogen, and chloro functionalities were introduced via epoxidation of the remaining double bond, ring-opening of epoxide, and cis-hydroxylation reactions. (C) 2014 Elsevier Ltd. All rights reserved.Cyclooctane-1,2,3,4-tetraols, aminocyclooctanetriol, and chlorocyclooctanetriol were synthesized starting from cis,cis-1,3-cyclooctadiene by a concise and efficient method. Cyclooctene endoperoxide and cyclooctene epoxide obtained by photooxygenation and epoxidation, respectively, of cis,cis-1,3-cyclooctadiene were used as the key intermediates. The other oxygen, nitrogen, and chloro functionalities were introduced via epoxidation of the remaining double bond, ring-opening of epoxide, and cis-hydroxylation reactions. (C) 2014 Elsevier Ltd. All rights reserved.Cyclooctane-1,2,3,4-tetraols, aminocyclooctanetriol, and chlorocyclooctanetriol were synthesized starting from cis,cis-1,3-cyclooctadiene by a concise and efficient method. Cyclooctene endoperoxide and cyclooctene epoxide obtained by photooxygenation and epoxidation, respectively, of cis,cis-1,3-cyclooctadiene were used as the key intermediates. The other oxygen, nitrogen, and chloro functionalities were introduced via epoxidation of the remaining double bond, ring-opening of epoxide, and cis-hydroxylation reactions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.08.060
• 作为产物：
  描述：

  环辛二烯 在 氧气 、 tetraphenylporphyrin 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 25.0~60.0 ℃ 、600.01 kPa 条件下， 反应 0.53h， 生成 9-Oxabicyclo<4.2.1>non-7-en-1-ol
  参考文献：
  名称：

  共轭二烯的连续内过氧化和随后的重排导致CH氧化的合成子

  摘要：

  我们已经研究了几种共轭二烯的连续流光氧化和随后使用实用且安全的连续流自制工程装置进行的重排。端到端的方法涉及内过氧化物氧化，Kornblum-DeLaMare重排以及其他重排，并通过优化，范围和扩大规模进行了详细说明，以获得有用的羟基烯酮，呋喃和1,4-二羰基结构单元。

  DOI：

  10.1021/acs.joc.8b01307

文献信息

• A Cleavable C₂-Symmetric <i>trans</i>-Cyclooctene Enables Fast and Complete Bioorthogonal Disassembly of Molecular Probes
  作者：Martin Wilkovitsch、Maximilian Haider、Barbara Sohr、Barbara Herrmann、Jenna Klubnick、Ralph Weissleder、Jonathan C. T. Carlson、Hannes Mikula

  DOI：10.1021/jacs.0c07922

  日期：2020.11.11

  (C2TCO) that exhibits excellent biological stability and can be rapidly and completely cleaved with functionalized alkyl-, aryl-, and H-tetrazines, irrespective of click orientation. By incorporation of C2TCO into fluorescent molecular probes, we demonstrate highly efficient extracellular and intracellular bioorthogonal disassembly via omnidirectional tetrazine-triggered cleavage.

  生物正交化学正在弥合静态化学连接和分子状态的动态生理调控之间的鸿沟，实现驱动多种技术的原位转化。尽管对机理的理解已经成熟，并且新的生物正交键-切割反应已经成熟，但分子 ON/OFF 控制的更广泛目标受到了现有系统无法实现快速（即几秒到几分钟，而不是几小时）和完全（即 >99%）切割的限制。为了获得高保真分子灭活所需的严格性能特征，我们设计并合成了一种新的 C2 对称反式环辛烯接头 （C2TCO），该接头表现出优异的生物稳定性，并且可以被官能化烷基、芳基和 H-四嗪快速完全裂解，而不受点击方向的影响。通过将 C2TCO 掺入荧光分子探针中，我们展示了通过全向 tetrazine 触发的切割实现高效的细胞外和细胞内生物正交分解。
• Palladium(0) catalyzed reaction of 1,3-diene 1,4-epiperoxides
  作者：M. Suzuki、Y. Oda、R. Noyori

  DOI：10.1016/s0040-4039(01)82971-3

  日期：1981.1

  Reaction of 1,3-diene 1,4-epiperoxides with Pd(PPh3)4 catalyst forms the corresponding 4-hydroxy enones, syn diepoxides, and 1,4-diols as the major products. The results are interpreted as being due to competing Pd(0)/Pd(II) and Pd(0)/Pd(I) exchange mechanisms.

  1,3-二烯1,4-环氧过氧化物与Pd（PPh 3）4催化剂的反应形成相应的4-羟基烯酮，顺式双环氧化合物和1,4-二醇为主要产物。结果被解释为归因于竞争的Pd（0）/ Pd（II）和Pd（0）/ Pd（I）交换机制。
• MAYER, WINFRIED;MEIER, HERBERT, CHEM. BER., 122,(1989) N, C. 509-517
  作者：MAYER, WINFRIED、MEIER, HERBERT

  DOI：——

  日期：——
• SUZUKI, M.;ODA, Y.;NOYORI, R., TETRAHEDRON LETT., 1981, 22, N 44, 4413-4416
  作者：SUZUKI, M.、ODA, Y.、NOYORI, R.

  DOI：——

  日期：——
• Continuous Endoperoxidation of Conjugated Dienes and Subsequent Rearrangements Leading to C–H Oxidized Synthons
  作者：Juliana M. de Souza、Timothy J. Brocksom、D.Tyler McQuade、Kleber T. de Oliveira

  DOI：10.1021/acs.joc.8b01307

  日期：2018.8.3

  We have investigated the continuous flow photooxidation of several conjugated dienes and subsequent rearrangement using a practical and safe continuous-flow homemade engineered setup. End-to-end approaches involving endoperoxidation, Kornblum–DeLaMare rearrangement, and additional rearrangements are comprehensively detailed with optimization, scope, and scale-up to obtain useful hydroxyenones, furans

  我们已经研究了几种共轭二烯的连续流光氧化和随后使用实用且安全的连续流自制工程装置进行的重排。端到端的方法涉及内过氧化物氧化，Kornblum-DeLaMare重排以及其他重排，并通过优化，范围和扩大规模进行了详细说明，以获得有用的羟基烯酮，呋喃和1,4-二羰基结构单元。