2-[(tetrahydropyran-2-yl)oxy]-3-chloroprop-1-ene | 161271-02-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-[(tetrahydropyran-2-yl)oxy]-3-chloroprop-1-ene
• 英文别名: 2[(tetrahydropyran-2-yl)oxy]allyl chloride；2-(3-chloroprop-1-en-2-yloxy)oxane
• CAS: 161271-02-9
• 化学式: C₈H₁₃ClO₂
• 分子量: 176.643
• InChiKey: ZIBCOPVVHAJDEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-[(tetrahydropyran-2-yl)oxy]-3-chloroprop-1-ene 在 四丁基硫酸氢铵 、 sodium carbonate 、 potassium iodide 作用下， 以 水 为溶剂， 反应 3.0h， 生成 3-iodo-2-(2-tetrahydropyranyloxy)propene
  参考文献：
  名称：

  Radical routes to indolizidines. Synthesis of (-)-slaframine

  摘要：

  The synthesis of (-)-slaframine (5) was executed in 11 steps and 25% overall yield from resolved 3(S)-hydroxy-4-pentenamide (22). Two cyclization reactions were used to form the indolizidine skeleton and also to provide the necessary stereocontrol at C-8a and C-6 of the natural product. "Iodolactamization" of 22 gave selectively the cis-pyrrolidinone 21. Later in the synthesis, a silane-mediated radical cyclization of the phenylseleno lactam 33 gave selectively the 6-alpha-hydroxyindolizidinone 35a, an event predictable from model studies-such as 14c --> 15c. Replacement of hydroxy with azido and reduction of the lactam carbonyl gave "slaframine azide", 38, a stable and easily convertible immediate precursor to 5.

  DOI：

  10.1021/jo00044a011
• 作为产物：
  描述：

  1,3-dichloro-2-(tetrahydropyran-2-yloxy) propane 在 氢氧化钾 、 四丁基硫酸氢铵 作用下， 以87%的产率得到2-[(tetrahydropyran-2-yl)oxy]-3-chloroprop-1-ene
  参考文献：
  名称：

  Radical routes to indolizidines. Synthesis of (-)-slaframine

  摘要：

  The synthesis of (-)-slaframine (5) was executed in 11 steps and 25% overall yield from resolved 3(S)-hydroxy-4-pentenamide (22). Two cyclization reactions were used to form the indolizidine skeleton and also to provide the necessary stereocontrol at C-8a and C-6 of the natural product. "Iodolactamization" of 22 gave selectively the cis-pyrrolidinone 21. Later in the synthesis, a silane-mediated radical cyclization of the phenylseleno lactam 33 gave selectively the 6-alpha-hydroxyindolizidinone 35a, an event predictable from model studies-such as 14c --> 15c. Replacement of hydroxy with azido and reduction of the lactam carbonyl gave "slaframine azide", 38, a stable and easily convertible immediate precursor to 5.

  DOI：

  10.1021/jo00044a011

文献信息

• Structural Insight into (2-Oxy-π-allyl)palladium and -platinum Complexes as Precursors of Oxodimethylenemethane Complexes
  作者：Akihiro Ohsuka、Tjandra W. Wardhana、Hideo Kurosawa、Isao Ikeda

  DOI：10.1021/om961108j

  日期：1997.6.1

  η3-allylpalladium and -platinum complexes bearing an acetal group at the 2-position [M(η3-CH2C(OCH2OCH3)CH2)(PPh3)2](PF6) (M = Pd (1a), Pt (1b)) and [M(η3-CH2C(O-2-C5H9O)CH2)(PPh3)2](PF6) (M = Pd (2a), Pt (2b))} reveal that they have a large contribution of oxonium structure, regardless of the kind of metal. Depending on the structure of the acetal moiety, these η3-allyl complexes show different reactivities

  η的X射线晶体结构3 π-烯丙基和-铂复合物在2-位带有缩醛基[M（η 3 -CH 2 C（OCH 2 OCH 3）CH 2）（PPH 3）2 ]（PF 6）（M = PD（1A），铂（1B））和[M（η 3 -CH 2 C（O-2-C 5 H ^ 9 O）CH 2）（PPH 3）2 ]（PF 6）（ M = Pd（2a），Pt（2b）））}揭示了它们与金属的种类无关，对氧结构的贡献很大。取决于缩醛部分的结构中，这些η 3 -烯丙基配合物表现出朝向氧化钾和甲醇离子作为亲核试剂的不同反应性。oxodimethylenemethane复合物的生成机制[M（η 3 -CH 2 C（O）CH 2）（PPH 3）2 ]（PF 6）（M = PD（图3a），铂（图3b））}从这些缩醛化合物根据X射线晶体结构，反应产物分析和18O同位素标记技术。在η的2位的亲核置换3个π-烯丙基配合物直接证明首次由同位素技术。