(S)-1-iodo-2-methyl-3-(tetrahydropyranyloxy)propane | 127483-89-0

• 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: (S)-1-iodo-2-methyl-3-(tetrahydropyranyloxy)propane
• 英文别名: 2-[(2S)-3-iodo-2-methylpropoxy]oxane
• CAS: 127483-89-0
• 化学式: C₉H₁₇IO₂
• 分子量: 284.137
• InChiKey: XMKWXNSBMXSYNA-VEDVMXKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：

  (S)-1-iodo-2-methyl-3-(tetrahydropyranyloxy)propane 在 六甲基磷酰三胺 、 正丁基锂 、 sodium amalgam 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 91.0h， 生成 (2R,6R)-2,6,10-trimethyl-1-(tetrahydropyranyloxy)undecane
  参考文献：
  名称：

  Mori, Kenji; Harada, Hironori; Zagatti, Pierre, Liebigs Annalen der Chemie, 1991, # 3, p. 259 - 267

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2(S)-methyl-3-tetrahydropyranyloxypropanoate 在 咪唑 、 lithium aluminium tetrahydride 、 碘 、 三苯基膦 作用下， 生成 (S)-1-iodo-2-methyl-3-(tetrahydropyranyloxy)propane
  参考文献：
  名称：

  General synthetic approach to bicyclo[9.3.0]tetradecenone: a versatile intermediate to clavulactone and clavirolides

  摘要：

  An efficient and stereoselective approach to the bicyclo[9.3.0]tetradecenone core structure of clavulactone starting from readily and abundantly available 2-methyl-1,3-cyclopentandione employing microbial desymmetrization and cyanohydrin alkylation as the key steps is described. The synthetic route described herein is applicable to the syntheses of the core structures of Clavirolides A-F. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.106

文献信息

• Stereochemistry of enacyloxins. Part 3.1 (12′S,17′R,18′S,19′R)-Absolute configuration of enacyloxins, a series of antibiotics from Frateuria sp. W-315
  作者：Ryo Takeuchi、Hiromasa Kiyota、Manabu Yaosaka、Toshihiko Watanabe、Keijiro Enari、Takeyoshi Sugiyama、Takayuki Oritani

  DOI：10.1039/b104341m

  日期：2001.10.11

  The absolute configuration of the 12′,17′,18′,19′-positions of enacyloxins (ENXs), a series of polyhydroxy-polyenic antibiotics from Frateuria sp. W-315, was determined. As degradation of decarbamoyl (dec) ENX IIa gave (5R,6S,1′E)-6-(but-1′-enyl)-5-chloro-5,6-dihydro-2H-pyran-2-one, which corresponded to the 15′–23′ skeleton of dec ENX IIa, its enantiomers were synthesized from tri-O-acetyl-D-glucal. Comparison of the HPLC retention time of these naturally derived and synthetic compounds revealed the 17′R,18′S,19′R-configuration of ENXs. Hydrogenation and oxidation of ENX IIa gave methyl 13-hydroxy-6,12-dimethyltridecanoate, which was converted to the 13-MTPA ester. Comparison of the 1H NMR chemical shifts and the coupling constants with the model compounds revealed the 12′S-configuration. This absolute stereochemistry is necessarily applicable to other enacyloxins.

  研究人员测定了烯酰环毒素（ENXs）的12â²,17â²,18â²,19â²-位的绝对构型，烯酰环毒素是来自弗氏菌W-315的一系列多羟基多烯抗生素。癸氨基甲酰基（癸）ENX IIa降解后得到(5R,6S,1â²E)-6-(丁-1â²-烯基)-5-氯-5,6-二氢-2H-吡喃-2-酮，与癸ENX IIa的15â²â23â²骨架相对应。通过比较这些天然衍生化合物和合成化合物的高效液相色谱保留时间，发现了ENXs的17â²R、18â²S、19â²R构型。ENX IIa 经氢化和氧化后得到 13-羟基-6,12-二甲基十三烷酸甲酯，并转化为 13-MTPA 酯。将 1H NMR 化学位移和耦合常数与模型化合物进行比较，发现了 12â²S-构型。这种绝对立体化学结构必然适用于其他烯丙菊酯。
• The total synthesis of 10-(R,S)-C30 botryococcene and botryococcane and a new synthesis of a general intermediate to the botryococcene family
  作者：Nicholas W. Hird、Thomas V. Lee、Alistair J. Leigh、James R. Maxwell、Torren M. Peakman

  DOI：10.1016/s0040-4039(01)80530-x

  日期：1989.1
• Toward a New Palmerolide Assembly Strategy: Synthesis of C16-C24
  作者：Gregory Dudley、Marilda Lisboa、Jeannie Jeong-Im、David Jones

  DOI：10.1055/s-0031-1290675

  日期：2012.6

  Asymmetric synthesis of C16-C24 of palmerolide A is described, featuring convergent Negishi coupling, Singaram propargylation, and successful tactical maneuvering to address an unexpected allylic substitution reaction.
• HIRD, NICHOLAS W.;LEE, THOMAS V.;LEIGH, ALISTAIR J.;MAXWELL, JAMES R.;PEA+, TETRAHEDRON LETT., 30,(1989) N6, C. 4867-4870
  作者：HIRD, NICHOLAS W.、LEE, THOMAS V.、LEIGH, ALISTAIR J.、MAXWELL, JAMES R.、PEA+

  DOI：——

  日期：——
• MORI, KENJI;HARADA, HIRONORI;ZAGATTI, PIERRE;CORK, ALAN;HALL, DAVID R., LIEBIGS ANN. CHEM.,(1991) N, C. 259-267
  作者：MORI, KENJI、HARADA, HIRONORI、ZAGATTI, PIERRE、CORK, ALAN、HALL, DAVID R.

  DOI：——

  日期：——