1-环丁烯-1-甲醇 | 89182-08-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-环丁烯-1-甲醇
• 英文名称: (1-cyclobutenyl)methyl alcohol
• 英文别名: 1-cyclobutenylmethanol；1-cyclobutenemethanol；cyclobut-1-enyl-methanol；Cyclobuten-(1)-yl-carbinol-(1)；Cyclobuten-(1)-yl-methanol；Cyclobut-1-enylmethanol；cyclobuten-1-ylmethanol
• CAS: 89182-08-1
• 化学式: C₅H₈O
• 分子量: 84.1179
• InChiKey: QKWQJULHSYOWGC-UHFFFAOYSA-N

物化性质

• 沸点：
  116-185 °C
• 密度：
  1.040±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  1-环丁烯-1-甲醇 在 甲醇 、 铂 作用下， 生成 环丁基甲醇
  参考文献：
  名称：

  Oxetanes. VIII. Synthesis and Reactions of 2-Oxaspiro[3,2]hexane^1,2

  摘要：

  DOI：

  10.1021/ja01523a045
• 作为产物：
  描述：

  1-环丁烯-1-羧酸 在 溴 、 sodium iodide 、 锌 作用下， 以 甲醇 、 四氯化碳 、 乙醚 为溶剂， 生成 1-环丁烯-1-甲醇
  参考文献：
  名称：

  Heyns,K. et al., Chemische Berichte, 1961, vol. 94, p. 1015 - 1025

  摘要：

  DOI：

文献信息

• Highly Enantioselective Copper-Catalyzed Alkylation of β-Ketoesters and Subsequent Cyclization to Spirolactones/Bi-spirolactones
  作者：Qing-Hai Deng、Hubert Wadepohl、Lutz H. Gade

  DOI：10.1021/ja211859w

  日期：2012.2.15

  Cu-catalyzed enantioselective alkylation of β-ketoesters using alcohols for in situ preparation of alkylating reagents is reported. A number of functionalized β-ketoesters containing a quaternary carbon stereocenter are obtained with up to 99% ee. The alkylation products derived from 2-substituted allylic alcohols or their corresponding iodides can then be converted to spirolactones, bi-spirolactones

  报道了使用醇对 β-酮酯进行 Cu 催化的对映选择性烷基化，用于原位制备烷基化试剂。获得了许多含有季碳立体中心的官能化 β-酮酯，ee 高达 99%。然后可以将衍生自 2-取代烯丙醇或其相应碘化物的烷基化产物转化为螺内酯、双螺内酯和相关的手性目标产物。
• Scope of the Ring-Opening Metathesis Polymerization (ROMP) Reaction of 1-Substituted Cyclobutenes
  作者：Airong Song、Jae Chul Lee、Kathlyn A. Parker、Nicole S. Sampson

  DOI：10.1021/ja1037098

  日期：2010.8.4

  carboxamides, and carbinol esters) were investigated as substrates for ring-opening metathesis polymerization (ROMP) with [(H(2)IMes)(3-Br-pyridine)(2)(Cl)(2)Ru=CHPh]. Both the secondary amides of 1-cyclobutenecarboxylic acid and the esters of 1-cyclobutene-1-methanol undergo polymerization. The secondary amides provide translationally invariant polymers (E-olefins). Although the carbinol esters yield stereo-

  研究了一系列 1-取代的环丁烯衍生物（羧酸酯、羧酰胺和甲醇酯）的反应性，作为开环复分解聚合 (ROMP) 与 [(H(2)IMes)(3-Br-吡啶) (2)(Cl)(2)Ru=CHPh]。1-环丁烯羧酸的仲酰胺和1-环丁烯-1-甲醇的酯都进行聚合。仲酰胺提供平移不变的聚合物（E-烯烃）。虽然甲醇酯产生立体和区域化学异质聚合物，但 1-环丁烯羧酸酯和叔酰胺进行开环复分解 (ROM) 但不进行 ROMP。在 B3LYP/6-31G* 和 LANL2DZ 理论水平上分析了这些 ROMP 和 ROM 反应的区域和立体化学结果。
• Resistance-Modifying Agents. 8. Inhibition of <i>O</i>⁶-Alkylguanine-DNA Alkyltransferase by <i>O</i>⁶-Alkenyl-, <i>O</i>⁶-Cycloalkenyl-, and <i>O</i>⁶-(2-Oxoalkyl)guanines and Potentiation of Temozolomide Cytotoxicity in Vitro by <i>O</i>⁶-(1-Cyclopentenylmethyl)guanine
  作者：Roger J. Griffin、Christine E. Arris、Christine Bleasdale、F. Thomas Boyle、A. Hilary Calvert、Nicola J. Curtin、Christine Dalby、Sreenivas Kanugula、Nicola K. Lembicz、David R. Newell、Anthony E. Pegg、Bernard T. Golding

  DOI：10.1021/jm000961o

  日期：2000.11.1

  A series of O-6-allyl- and O-6-(2-oxoalkyl)guanines were synthesized and evaluated, in comp ari son with the corresponding O-6-alkylguanines, as potential inhibitors of the DNA-repair protein O-6-alkylguanine-DNA alkyltransferase (AGT). Simple O-6-alkyl- and O-6-cycloalkylguanines were weak AGT inactivators compared with O-6-allylguanine (IC50 = 8.5 +/- 0.6 muM) With IC50 values ranging from 100 to 1000 muM. The introduction of substituents at C-2 of the allyl group of O-6-allylguanine reduced activity compared with the parent compound, while analogous compounds in the O-6-(2-oxoalkyl)guanine series exhibited very poor activity (150-1000 muM) O-6-Cycloalkenylguanines proved to be excellent AGT inactivators, with 1-cyclobutenylmethylguanine (IC50 = 0.55 +/- 0.02 muM) and 1-cyclopentenylmethylguanine (IC50 = 0.39 +/- 0.04 muM) exhibiting potency approaching that of the benchmark AGT inhibitor O-6-benzylguanine (IC50 = 0.18 +/- 0.02 muM). 1-Cyclopentenylmethylguanine also inactivated AGT in intact HT29 human colorectal carcinoma cells (IC50 = 0.20 +/- 0.07 muM) and potentiated the cytotoxicity of the monomethylating antitumor agent Temozolomide by approximately 3- and 10-fold, respectively, in the HT29 and Colo205 tumor cell lines. The observation that four mutant AGT enzymes resistant to O-6-benzylguanine also proved strongly cross-resistant to 1-cyclopentenylmethylguanine indicates that the O-6-substituent of each compound makes similar binding interactions within the active site of AGT.
• Alicyclic Alkylamines and Alkanolamines
  作者：Alfred Burger、Robert T. Standridge、Nils E. Stjernström、Paolo Marchini

  DOI：10.1021/jm50019a011

  日期：1961.12
• Synthesis of Isoquinoline Derivatives Using ROM−RCM of Cyclobutene-yne
  作者：Miwako Mori、Hideaki Wakamatsu、Keisuke Tonogaki、Reiko Fujita、Tsuyoshi Kitamura、Yoshihiro Sato

  DOI：10.1021/jo048214c

  日期：2005.2.1

  Isoquinoline derivatives were synthesized from cyclobuten-ylmethylamine derivatives having an alkyne moiety in a tether using a second-generation ruthenium carbene complex under ethylene gas in good yields.