4-<(benzyloxy)methyl>cyclohexene | 145827-23-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-<(benzyloxy)methyl>cyclohexene
• 英文别名: 4-(benzyloxymethyl)cyclohex-1-ene；Cyclohex-3-en-1-ylmethoxymethylbenzene
• CAS: 145827-23-2
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: STVLAPIFUGZUNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-<(benzyloxy)methyl>cyclohexene 在 吡啶 、 盐酸 、 叔丁基过氧化氢 、 potassium tert-butylate 、 lithium perchlorate 、 四氯化钛 作用下， 以 乙醇 、 苯 为溶剂， 反应 33.25h， 生成 c-4-<(benzyloxy)methyl>-t-2-methoxyy-r-1-cyclohexanol
  参考文献：
  名称：

  Regiochemical control of the ring-opening of 1,2-epoxides by means of chelating processes. 2. Synthesis and reactions of the cis- and trans-oxides of 4-[(benzyloxy)methyl]cyclohexene, 3-cyclohexenemethanol, and methyl 3-cyclohexenecarboxylate

  摘要：

  The synthesis of the diastereoisomeric epoxides cis-1b-d and trans-2b-d and the products of their ring-opening by various nucleophiles are described. The results of the ring-openings of the trans-epoxides 2b-d can be rationalized by combining stereoelectronic and conformational arguments. However, the regioselectivity of the ring-openings of the cis-epoxides 1b-d can, in principle, be influenced by the chelation of a metal ion by the oxygen atom of the epoxy group and that of the substituent on the 4-position. The results of the reactions of the cis-epoxides 1b-d indicate that, to some degree, chelation is indeed a factor. How important a factor it is is dependent both on the reaction conditions and on the concentration and nature of the metal ion. In the ring-openings of the cis-epoxides 1b and 1d, chelation seems to be a larger factor than it is in the ring-openings of cis-epoxide 1c. However, in no case is chelation as large a factor as it was in the ring-openings of the cis-epoxide 1a, which was studied earlier. On the other hand, the autocatalyzed methanolysis, under neutral conditions, of epoxy acid 1e, followed by CH2N2 methylation of the crude product, afforded a mixture of the two regioisomeric hydroxy ethers in which the C-2-type compound predominates. This result suggests that intramolecular hydrogen bonding may determine the reactive conformation of 1e.

  DOI：

  10.1021/jo00031a018
• 作为产物：
  描述：

  3-环己烯-1-甲醇 、 溴甲苯 在 sodium hydride 作用下， 生成 4-<(benzyloxy)methyl>cyclohexene
  参考文献：
  名称：

  Synthesis of diacylglycerol analogues as potential second-messenger antagonists and inhibitors of protein kinase C

  摘要：

  A series of analogues of diacylglycerol has been prepared and tested as inhibitors of protein kinase C (PKC). The diketone analogues, 10-hydroxymethyl-8,13-eicosanedione (24), 10-acetoxymethyl-8,13-eicosanedione (25), and 10-methoxymethyl-8,13-eicosanedione (26) each inhibited PKC activated by 2-0-acetyl-1-0-oleoylglycerol. Compound 24 was the most effective inhibitor of the growth of MR4 and HT29 cells in culture, and 26 was more effective than 24 against HL60 cells.

  DOI：

  10.1016/0008-6215(92)85036-y

文献信息

• 用于生物正交反应的双环[4.1.0]庚烷亚硝基 脲衍生物及其制备方法与应用
  申请人：清华大学

  公开号：CN111138337B

  公开（公告）日：2021-06-22

  本发明公开了一种用于生物正交反应的双环[4.1.0]庚烷亚硝基脲衍生物及其制备方法与应用。结构式如式Ⅰ所示，R表示碳原子数为1～15的烷基、碳原子数为6～15的芳基或H；X表示O或N；n为1～10之间的自然数。本发明首次提供了pH引发的反式环庚烯与四嗪的IEDDA反应，并可作为生物正交反应。本发明通过引入双环亚硝基脲衍生物—双环[4.1.0]庚烷亚硝基脲衍生物作为储存和释放反式环庚烯的前体，即利用了反式环庚烯的高活性，又尽量避免了其不稳定性。本发明提供的pH引发的生物正交反应能够应用于体外蛋白标记、活细胞成像和组织的预标记成像，同时也能应用于活体动物肿瘤预标记成像。
• Chemical trigger-enabled bioconjugation reaction
  作者：Fayang Xie、Xiangqian Jia、Zhu Zhu、Yunfei Wu、Haolin Jiang、Hongzhi Yang、Yu Cao、Rui Zhu、Bing Zhou、Juanjuan Du、Yefeng Tang

  DOI：10.1039/d1ob01177d

  日期：——

  cycloaddition of trans-cycloheptene (TCH) with tetrazine. Unlike the conventional strain-promoted bioconjugation reactions that utilize built-in strained alkenes as reactants, the current one features a “trigger-release-conjugate” reaction model, in which a highly strained TCH species is released from a bench-stable bicyclic N-nitrosourea (BNU) derivative upon treatment with an external stimulus. It is noteworthy

  开发概念新颖且实用的生物共轭反应一直是化学生物学研究的强烈追求。在此，我们报告了一种前所未有的生物共轭反应，该反应取决于反式环庚烯（TCH）与四嗪的化学触发反电子需求狄尔斯-阿尔德（IEDDA）环加成反应。与利用内置应变烯烃作为反应物的传统应变促进生物共轭反应不同，当前的生物共轭反应具有“触发-释放-共轭”反应模型，其中高度应变的TCH物质从工作台稳定的双环N-中释放出来。外部刺激后产生亚硝基脲（BNU）衍生物。值得注意的是，BNU 衍生物的反应性-稳定性平衡可以通过操纵其 N-1 取代基来调节。作为概念验证案例，这种新的化学触发 IEDDA 反应已应用于体外蛋白质标记和预靶向细胞成像。这项工作开辟了利用 BNU 衍生物作为生物共轭化学中新型化学报告分子的新途径。
• Deprotection of benzyl and p-methoxybenzyl ethers by chlorosulfonyl isocyanate–sodium hydroxide
  作者：Ji Duck Kim、Gyoonhee Han、Ok Pyo Zee、Young Hoon Jung

  DOI：10.1016/s0040-4039(02)02648-5

  日期：2003.1

  CSI-NaOH procedure provided a new and mild methodology for the deprotection of benzyl and p-methoxybenzyl ethers without affecting the other functional groups under similar reaction conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis of diacylglycerol analogues as potential second-messenger antagonists and inhibitors of protein kinase C
  作者：Josie C. Briggs、Alan H. Haines、Richard J.K. Taylor、Alan P. Dawson、I. Gibson、Jackie Hook、Alan Lloyd、Silkie Meiners

  DOI：10.1016/0008-6215(92)85036-y

  日期：1992.10

  A series of analogues of diacylglycerol has been prepared and tested as inhibitors of protein kinase C (PKC). The diketone analogues, 10-hydroxymethyl-8,13-eicosanedione (24), 10-acetoxymethyl-8,13-eicosanedione (25), and 10-methoxymethyl-8,13-eicosanedione (26) each inhibited PKC activated by 2-0-acetyl-1-0-oleoylglycerol. Compound 24 was the most effective inhibitor of the growth of MR4 and HT29 cells in culture, and 26 was more effective than 24 against HL60 cells.
• A selective resin for trans-diequatorial-1,2-diols
  作者：Emilio Lence、Luis Castedo、Concepción González-Bello

  DOI：10.1016/j.tetlet.2009.01.157

  日期：2009.4

  A selective resin for linking trans-diequatorial-1,2-diols to solid support is described. This linking was carried out under mild and aprotic conditions involving the use of trimethylsilyl methyl ether in the presence of trimethylsilyl trifluoromethanesulfonate. Cleavage from the resin was also carried out under mild conditions by treatment with dichloromethane/trifluoroacetic acid/water (21:20:1). The usefulness of the described cyclohexane-1,2-diketone resin 7 in quinic acid chemistry was also studied. (C) 2009 Elsevier Ltd. All rights reserved.