1,3-dichloro-2-(tetrahydropyran-2-yloxy) propane | 28659-12-3

• 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: 1,3-dichloro-2-(tetrahydropyran-2-yloxy) propane
• 英文别名: 1,3-dichloro-2-(6-(3,4,5,6-tetrahydro-2H-pyranoxy))propane；1,3-Dichlor-propanol(2)-THP-ether；1.3-Bichlor-2-tetrahydropyranyloxypropan；2-(2-chloro-1-chloromethyl-ethoxy)-tetrahydro-pyran；2-(1,3-Dichloropropan-2-yloxy)oxane
• CAS: 28659-12-3
• 化学式: C₈H₁₄Cl₂O₂
• 分子量: 213.104
• InChiKey: IWOGZVBDIWOKHM-UHFFFAOYSA-N

物化性质

• 沸点：
  68 °C(Press: 1 Torr)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  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
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 1,3-二氯丙醇 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到1,3-dichloro-2-(tetrahydropyran-2-yloxy) propane
  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

• C11H2 Hydrocarbons—I
  作者：J.F. Monthony、W.H. Okamura

  DOI：10.1016/s0040-4020(01)88950-x

  日期：1972.1

  Cyclooctatetraene dianion was condensed with 1,3-dichloro-2-tetrahydropyranyloxypropane to afford tricyclic ether 8a, which was converted in three steps to the C11H12 hydrocarbon 4a. The latter fragments readily to benzene and cyclopentadiene upon thermolysis and upon direct or sensitized photolysis. The dianion reacted with 1,2,3-trichloropropane in a surprising way to afford the cyclobutane derivative

  将环辛酸酯二烯二阴离子与1,3-二氯-2-四氢吡喃基氧基丙烷缩合，得到三环醚8a，将其三步转化为C 11 H 12烃4a。后者在热解时以及在直接或敏化的光解时易于裂解成苯和环戊二烯。二价阴离子与1,2,3-三氯丙烷反应出人意料，从而得到环丁烷衍生物13。
• Alternative dimerisation reagents for synthesis of iodixanol
  申请人：GE Healthcare AS

  公开号：EP2281802A1

  公开（公告）日：2011-02-09

  This invention relates to the synthesis of iodixanol. In particular, it relates to alternative dimerisation reagents in the conversion of 5-acetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide ("Compound A") to iodixanol.

  这项发明涉及碘普利的合成。具体来说，它涉及在将5-乙酰氨基-N，N'-双(2,3-二羟基丙基)-2,4,6-三碘异苯二酰胺（"化合物A"）转化为碘普利时的替代二聚试剂。
• Higgins, Robert H.; Eaton, Quentin L.; Worth, Leroy, Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 255 - 259
  作者：Higgins, Robert H.、Eaton, Quentin L.、Worth, Leroy、Peterson, Myra V.

  DOI：——

  日期：——
• Singh, Alok; Sikder, Nirmala; Sikder, Arun K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 12, p. 2560 - 2563
  作者：Singh, Alok、Sikder, Nirmala、Sikder, Arun K.

  DOI：——

  日期：——
• HIGGINS, R. H.;EATON, Q. L.;WORTH, L. , JR.;PETERSON, M. V., J. HETEROCYCL. CHEM., 24,(1987) N 1, 255-259
  作者：HIGGINS, R. H.、EATON, Q. L.、WORTH, L. , JR.、PETERSON, M. V.

  DOI：——

  日期：——