2-benzyloxymethyl-4,5-dihydrofuran | 107757-75-5

• 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: 2-benzyloxymethyl-4,5-dihydrofuran
• 英文别名: 5-benzyloxymethyl-2,3-dihydrofuran；5-(phenylmethoxymethyl)-2,3-dihydrofuran
• CAS: 107757-75-5
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: HKWZOILKOFYBOG-UHFFFAOYSA-N

物化性质

• 沸点：
  282.5±29.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-benzyloxymethyl-4,5-dihydrofuran 以54%的产率得到
  参考文献：
  名称：

  MIYAZAKI, HIDEKI;OHKAWA, NOBUYUKI;NAKAMURA, NORIO;ITO, TOMIYOSHI;SADA, TO+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 2379-2390

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5-dihydrofuryl alcohol 以11%的产率得到
  参考文献：
  名称：

  MIYAZAKI, HIDEKI;OHKAWA, NOBUYUKI;NAKAMURA, NORIO;ITO, TOMIYOSHI;SADA, TO+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 2379-2390

  摘要：

  DOI：

文献信息

• Lactone and cyclic ether analogues of platelet-activating factor. Synthesis and biological activities.
  作者：Hideki MIYAZAKI、Nobuyuki OHKAWA、Norio NAKAMURA、Tomiyoshi ITOU、Toshio SADA、Takeshi OSHIMA、Hiroyuki KOIKE

  DOI：10.1248/cpb.37.2379

  日期：——

  Six-membered lactone and tetrahydropyran analogues of platelet-activating factor (PAF), 4-11, and related antagonistic derivatives 41-46 were synthesized. None of the δ-lactones 4-7 showed PAF-like activities, while the corresponding cyclic ethers 8, 9 and 11 were slightly active. Some of the cyclic antagonists showed more potent inhibitory activities than the open chain antagonist CV-3988 against platelet aggregation (rabbit platelet-rich plasma, IC50) and hypotension (rat, DI50) induced by C16-PAF : e.g. dl-3-6-[O-(trans-3-heptadeclcarbamoyloxytetrahydropyran-2-yl)methyl]phosphonoxy}hexylthiazolium (inner salt)(4ld)(IC505.5×10-7M, ID500.046mg/kg, i.v.);dl-3-5-[O-(cis-3-heptadecylcarbamoylthiotetrahydropyran-2-yl)methyl]phosphonoxy}pentylthiazolium (inner salt) (43c) (IC505.7×10-7M, ID500.076mg/kg, i.v.).

  合成了六元内酯和四氢呋喃类的血小板激活因子（PAF）类似物4-11以及相关的拮抗衍生物41-46。没有发现δ-内酯4-7显示出PAF样活性，而对应的环醚8、9和11则表现出轻微活性。一些环状拮抗剂在抑制由于C16-PAF引起的血小板聚集（兔血小板富集血浆，IC50）和低血压（大鼠，DI50）方面的活性比开链拮抗剂CV-3988更强。例如，dl-3-6-[O-(trans-3-十七烷基氨基甲酰氧基四氢呋喃-2-基)甲基]磷酸氧基}己基噻唑镁(内盐)(4ld)(IC50为5.5×10^-7M，ID50为0.046mg/kg，静脉注射)；dl-3-5-[O-(cis-3-十七烷基氨基甲酰基硫四氢呋喃-2-基)甲基]磷酸氧基}戊基噻唑镁(内盐)(43c)(IC50为5.7×10^-7M，ID50为0.076mg/kg，静脉注射)。
• Asymmetric routes to azasugars from chiral bicyclic lactams. Synthesis of 1,4-dideoxy-1,4-imino-D-lyxitol; L-deoxymannojirimycin; rhammo-1-deoxynojirimycin and 1-deoxy-6-epicastanospermine
  作者：A.I Meyers、Charles J Andres、James E Resek、Charlotte C Woodall、Maureen A McLaughlin、Peter H Lee、David A Price

  DOI：10.1016/s0040-4020(99)00454-8

  日期：1999.7

  By employing the appropriate chiral bicyclic lactams, the asymmetric total synthesis of four enantiopure azasugars mentioned in the title were successfully achieved. A series of diastereoselective oxidations () followed by diastereoselective reductions (BH3, 9-BBN) gave good yields of the trisubstituted (16) and tetrasubstituted (2,3,4) pyrrolidine and piperidines respectively.

  通过使用合适的手性双环内酰胺，成功实现了标题中提到的四种对映纯氮杂糖的不对称全合成。一系列非对映选择性氧化（的），接着加入非对映选择性的减少（BH 3，9-BBN），得到三取代（的良好产率16）和四取代的（2,3,4）吡咯烷和哌啶分别。
• Cyclic ether derivatives and their use
  申请人：Sankyo Company Limited

  公开号：US04891363A1

  公开（公告）日：1990-01-02

  Compounds of formula (I): ##STR1## (wherein: l is 2-4; A and B are oxygen or sulfur; one of R.sup.1 and R.sup.2 represents a long chain alkyl, alkylcarbamoyl or aliphatic acyl group and the other of R.sup.1 and R.sup.2 represents a group of formula (III) or (II.sub.f): ##STR2## in which E represents a single bond, a bivalent heterocyclic group or a group of formula --CO--, --COO-- or --CONR.sup.6 --, where R.sup.6 is hydrogen or an imino-protecting group; m is 0-3; n is 0-10; q is 0 or 1; R.sup.4 is optionally protected hydroxy, mercapto group or carboxy; Q is an amino or nitrogen-containing heterocyclic group; R.sub.f.sup.4 R.sub.f.sup.5 and R.sub.f.sup.6 are independently selected from the group consisting of hydrogen atoms and C.sub.1 -C.sub.6 alkyl groups, or R.sub.f.sup.4 and R.sub.f.sup.5 or R.sub.f.sup.4, R.sub.f.sup.5 and R.sub.f.sup.6, together with the nitrogen atom to which they are attached, form a heterocyclic ring) are PAF antagonists which may be used to treat asthma, hypotension, inflammation and shock. They may be prepared by reacting the corresponding compound having a haloalkyl phosphate ester or alkylenephosphate ester group in place of the ammonioalkyl phosphate ester group with an appropriate amine.

  公式（I）的化合物：其中：l为2-4；A和B为氧或硫；R.sup.1和R.sup.2中的一个代表长链烷基、烷基羰胺或脂肪酰基，另一个代表公式（III）或（II.sub.f）的基团：其中E代表单键、二价杂环基团或公式--CO--、--COO--或--CONR.sup.6--的基团，其中R.sup.6为氢或亚胺保护基；m为0-3；n为0-10；q为0或1；R.sup.4为可选择的保护羟基、巯基或羧基；Q为氨基或含氮杂环基团；R.sub.f.sup.4、R.sub.f.sup.5和R.sub.f.sup.6分别从氢原子和C.sub.1-C.sub.6烷基组成的群中独立选择，或R.sub.f.sup.4和R.sub.f.sup.5或R.sub.f.sup.4、R.sub.f.sup.5和R.sub.f.sup.6与它们连接的氮原子一起形成杂环环）是可用于治疗哮喘、低血压、炎症和休克的PAF拮抗剂。它们可以通过将具有卤代烷基磷酸酯或烷基磷酸酯基团代替氨基磷酸酯基团的相应化合物与适当的胺反应而制备。
• Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides
  作者：Mileina Jaffer、Abdelaziz Ebead、Edward Lee-Ruff

  DOI：10.3390/molecules15063816

  日期：——

  nucleoside analogues are reported. Both syntheses involve a key photochemical ring-expansion of cyclobutanones to an oxacarbene and its subsequent scavenging by 6-chloropurine. The synthesis of a bicyclic (locked) purine starts from a oxabicycloheptanone with a hydroxymethyl pendant. The preparation of an isonucleoside uses a cyclobutanone with an α-substituted 6-chloropurine. Irradiation of the latter produces

  报道了两种核苷类似物的制备。两种合成都涉及环丁酮向氧杂碳烯的关键光化学扩环，以及随后被 6-氯嘌呤清除。双环（锁定）嘌呤的合成从带有羟甲基侧链的氧杂双环庚酮开始。异核苷的制备使用环丁酮和 α-取代的 6-氯嘌呤。后者的辐照产生异核苷和无环核苷类似物。
• Phosphate ester derivatives, their preparation and their therapeutic use
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0210804A1

  公开（公告）日：1987-02-04

  Compounds of formula (I): (wherein m is 2-4, A and B are oxygen or sulfur and one of R' and R2 represents a long chain alkylcarbamoyl group and the other represents an ammonioalkyl phosphate ester group) are PAF antagonists which may be used to treat asthma, hypotension, inflammation and shock. They may be prepared by reacting the corresponding compound having a haloalkyl phosphate ester or alkylenephosphate ester group in place of the ammonioalkyl phosphate ester group with an appropriate amine.

  式（I）化合物： (其中 m 为 2-4，A 和 B 为氧或硫，R'和 R2 中的一个代表长链烷基氨基甲酰基，另一个代表氨代烷基磷酸酯基）是 PAF 拮抗剂，可用于治疗哮喘、低血压、炎症和休克。制备方法是将具有卤代烷基磷酸酯或烷基磷酸酯基团以取代氨代烷基磷酸酯基团的相应化合物与适当的胺反应。