4-Phenyltetrahydrofuran-2-ol | 128372-48-5

• 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-Phenyltetrahydrofuran-2-ol
• 英文别名: 3-Phenyl-5-hydroxy-tetrahydrofuran；4-phenyloxolan-2-ol
• CAS: 128372-48-5
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: ASAVHSGFIJMWIC-UHFFFAOYSA-N

物化性质

• 沸点：
  295.7±40.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  4-Phenyltetrahydrofuran-2-ol 在 Celite 、 silver carbonate 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以93%的产率得到4-苯基四氢呋喃-2-酮
  参考文献：
  名称：

  β-Vinyl-γ-butyrolactones via the palladium-catalysed reaction of vinyl triflates with Z-2-buten-1,4-diol

  摘要：

  The palladium-catalysed reaction of vinyl triflates with Z-2-buten-1,4-diol affords beta-vinyl-gamma-butyrolactols (4-vinyl-2-hydroxy-tetrahydrofurans) which are converted into the corresponding beta-vinyl-gamma-butyrolactones by a smooth oxidation with Ag2CO3 on celite. Preparation of beta-substituted-gamma-butyrolactones can be performed without the isolation of the intermediate gamma-butyrolactols, thus simplifying the procedure and usually with higher overall yields. The outcome of the palladium-catalysed formation of beta-substituted-gamma-butyrolactols strongly depends on the nature of the added base. Best results are obtained by using NaHCO3 or K2CO3 in the presence of n-Bu4NCl or TEBA.

  DOI：

  10.1016/s0040-4020(01)86427-9
• 作为产物：
  描述：

  4-苯基四氢呋喃-2-酮 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-Phenyltetrahydrofuran-2-ol
  参考文献：
  名称：

  S N 2-共轭加成序列的正式[4 +1]-和[5 +1]-环化：高度取代的碳环化合物的立体选择性合成。

  摘要：

  K 2 CO 3介导的6-溴-2-庚酸和7-溴-2-庚酸与活性亚甲基化合物的反应分别通过一系列S N 2-共轭加成反应（分别为[ 4 + 1]-和[5 +1]-环形）以非对映选择性的方式进行。

  DOI：

  10.1021/ol301044e

文献信息

• On the Stereoselectivity of γ-Lactol Substitutions with Allyl- and Propargylsilanes − Synthesis of Disubstituted Tetrahydrofuran Derivatives
  作者：Andreas Schmitt、Hans-Ulrich Reißig

  DOI：10.1002/1099-0690(200012)2000:23<3893::aid-ejoc3893>3.0.co;2-e

  日期：2000.12

  Monosubstituted γ-lactols 1a−1c, 3a−3c and 4a−4c, as well as disubstituted γ-lactol 5 and the γ-hydroxy-substituted γ-lactone 6, were transformed into disubstituted tetrahydrofuran derivatives by treatment with allyl- and propargylsilanes in the presence of Lewis acids. The diastereoselectivities were moderate to excellent and are interpreted by application of the Felkin−Anh model to cyclic oxocarbenium

  单取代的 γ-乳醇 1a-1c、3a-3c 和 4a-4c，以及双取代的 γ-乳醇 5 和 γ-羟基取代的 γ-内酯 6，通过用烯丙基-和炔丙基硅烷处理转化为双取代的四氢呋喃衍生物。路易斯酸的存在。非对映选择性中等至极好，可以通过将 Felkin-Anh 模型应用于环状氧碳鎓离子来解释。讨论了中间体构象异构体之间平衡的影响。在此基础上可以解释 4-取代 γ-内酯 3 令人惊讶的高非对映选择性。
• [EN] AVB3 AND AVB5 INTEGRIN ANTAGONISTS AND METHODS OF TREATING DISEASES OR CONDITIONS ASSOCIATED WITH AVB3 AND AVB5 INTEGRINS<br/>[FR] ANTAGONISTES DES INTEGRINES DOLLAR G(A)V DOLLAR G(B)3 ET DOLLAR G(A)V DOLLAR G(B)5 ET PROCEDES DE TRAITEMENT DE MALADIES ET ETATS ASSOCIES AUX INTEGRINES DOLLAR G(A)V DOLLAR G(B)3 ET DOLLAR G(A)V DOLLAR G(B)5
  申请人：BAYER AG

  公开号：WO2003059872A1

  公开（公告）日：2003-07-24

  This invention relates to compounds having the formula (I) wherein w, x, y, D, L, Q, R, R7 and R¿11? are as defined in the specification. The compounds habe been found to be αvß3 and/or αvß5 integrin antagonists. Pharmaceutical compositions containing the compounds, methods of making them, and methods of treatment of conditions associated with the αvß3 integrin or αvß5 integrin by administering a therapeutically effective amount of the compounds are also described.

  本发明涉及具有公式（I）的化合物，其中w、x、y、D、L、Q、R、R7和R¿11?的定义如规范中所述。已发现这些化合物是αvß3和/或αvß5整合素拮抗剂。还描述了含有这些化合物的药物组合物、制造它们的方法以及通过给予这些化合物的治疗有效量来治疗与αvß3整合素或αvß5整合素相关的疾病的方法。
• A Redox-Relay Heck Approach to Substituted Tetrahydrofurans
  作者：Tom J. M. Byrne、Megan E. Mylrea、James D. Cuthbertson

  DOI：10.1021/acs.orglett.3c00769

  日期：——

  An operationally simple and efficient strategy for the synthesis of substituted tetrahydrofurans from readily available cis-butene-1,4-diol is described. A redox-relay Heck reaction is used to rapidly access cyclic hemiacetals that can be directly reduced to afford the corresponding 3-aryl tetrahydrofuran. Furthermore, the hemiacetals can also serve as precursors to a range of disubstituted tetrahydrofurans

  描述了一种操作简单且有效的策略，用于从现成的顺式-丁烯-1,4-二醇合成取代的四氢呋喃。氧化还原中继 Heck 反应用于快速获得可直接还原以提供相应的 3-芳基四氢呋喃的环状半缩醛。此外，半缩醛还可以作为一系列二取代四氢呋喃的前体，包括花萼天然产物。
• CYCLIC HEMIACETAL COMPOUND PRODUCTION METHOD
  申请人：Kuraray Co., Ltd.

  公开号：EP3822261A1

  公开（公告）日：2021-05-19

  Provided is a method for producing a specific hemiacetal compound, the method including reacting a specific alcohol having an unsaturated bond, carbon monoxide, and hydrogen in the presence of a compound of Group 8 to Group 10 transition metal, a tertiary phosphite ligand, and a base, wherein an A value represented by the equation (1) is 0.0 to 4.0, and a B value represented by the equation (2) is 0.6 to 1.0.

  本发明提供了一种生产特定半缩醛化合物的方法，该方法包括使具有不饱和键的特定醇、一氧化碳和氢在第 8 族至第 10 族过渡金属化合物、叔亚磷酸酯配体和碱的存在下反应，其中式（1）表示的 A 值为 0.0 至 4.0，式（2）表示的 B 值为 0.6 至 1.0。
• Schmitt, Andreas; Reissig, Hans-Ulrich, Chemische Berichte, 1995, vol. 128, # 9, p. 871 - 876
  作者：Schmitt, Andreas、Reissig, Hans-Ulrich

  DOI：——

  日期：——