1-Iodo-4-(tetrahydropyranyloxy)-1-butyne | 123613-40-1

• 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-Iodo-4-(tetrahydropyranyloxy)-1-butyne
• 英文别名: tetrahydro-2-(4-iodobut-3-ynyloxy)-2H-pyran；4-iodo-1-(tetrahydro-2H-2-pyranyloxy)but-3-yne；1-iodo-4-tetrahydropyranyloxybutyne；2-(4-Iodobut-3-ynoxy)oxane
• CAS: 123613-40-1
• 化学式: C₉H₁₃IO₂
• 分子量: 280.106
• InChiKey: JSKHPEZDACFKOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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-Iodo-4-(tetrahydropyranyloxy)-1-butyne 在 sodium acetate 、 对甲苯磺酰肼 、 copper(I) bromide 、 锌 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 生成 diethyl [(Z)-1,1-difluoro-5-(tetrahydro-2H-2-pyranyloxy)-2-pentenyl]phosphonate
  参考文献：
  名称：

  Synthesis of 1,1-difluoro-5-(1H-9-purinyl)-2-pentenylphosphonic acids and the related methano analogues. Remarkable effect of the nucleobases and the cyclopropane rings on inhibitory activity toward purine nucleoside phosphorylase

  摘要：

  A series of 1,1-difluoro-5-(1H-9-purinyl)-2-pentenylphosphonic acids, (E)-2a,b and (Z)-2a,b, as well as the related methano analogues (+/-)-3a,b and (+/-)-4a,b were prepared for evaluation of their PNP inhibitory activities. The cyclopopane ring and the hypoxanthine residue were found to increase the profile of inhibitory activity. The IC50 and K-i values of difluoro({1R*,2S*)-2-[2-(6-oxo-6,9-dihydro-1H-9-purinyl)ethyl]cyclopropyl)methylphosphonic acid (+/-)3b toward PNP purified from Cellulomonas sp. were determined to be 70 nM and 8.8 nM, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)80023-0
• 作为产物：
  描述：

  2-(3-丁炔氧基)四水-2H-吡喃 在 正丁基锂 、 碘 作用下， 以 乙醚 为溶剂， 以92%的产率得到1-Iodo-4-(tetrahydropyranyloxy)-1-butyne
  参考文献：
  名称：

  改进的（14 E）-和（14 Z）-脱氢甲苯甲酸甲酯的合成：植物和真菌聚乙炔生物合成中的关键中间体

  摘要：

  已经实现了脱氢crepenynate的（14 E）-和（14 Z）异构体的高效合成。关键步骤包括在C14和C15之间提供C CC双键的Pd催化交叉偶联反应，然后进行Wittig反应，以在C9处构建（Z）烯烃。两种异构体均具有较高的总收率和立体选择性。

  DOI：

  10.1016/s0040-4039(01)00577-9

文献信息

• Development of a Potent and Selective HDAC8 Inhibitor
  作者：Oscar J. Ingham、Ronald M. Paranal、William B. Smith、Randolph A. Escobar、Han Yueh、Tracy Snyder、John A. Porco、James E. Bradner、Aaron B. Beeler

  DOI：10.1021/acsmedchemlett.6b00239

  日期：2016.10.13

  A novel, isoform-selective inhibitor of histone deacetylase 8 (HDAC8) has been discovered by the repurposing of a diverse compound collection. Medicinal chemistry optimization led to the identification of a highly potent (0.8 nM) and selective inhibitor of HDAC8.

  通过改变多种化合物的用途，发现了一种新型的，组蛋白脱乙酰基酶8（HDAC8）的同工型选择性抑制剂。药物化学的优化导致鉴定出了一种高效（0.8 nM）的HDAC8选择性抑制剂。
• Oligosaccharide Analogues of Polysaccharides. Part 5. Studies on the cross-coupling of alkynes and haloalkynes
  作者：Chengzhi Cai、Andrea Vasella

  DOI：10.1002/hlca.19950780814

  日期：1995.12.13

  The cross-coupling of the homopropargylic ether 1 and the halopropargylic ethers 2a and 2b was optimized, and aspects of the coupling mechanism were studied. Coupling promoted by Pd° and Cu1 in the presence of an amine yielded a mixture of the heterodimer 3 and the homodimers 4 and 5 (Scheme 1). Optimizations were first directed at suppressing homo-coupling. Homo-coupling is partially due to a H/I

  优化了均炔丙基醚1与卤代炔丙基醚2a和2b的交叉偶联，并研究了偶联机理。在胺存在下由Pd°和Cu 1促进的偶联产生异二聚体3与同二聚体4和5的混合物（方案1）。优化首先针对抑制均相耦合。同质耦合部分是由于H / I交换（1 + 2a⇌6 + 7）由CuI和一种胺促进。在DMSO中，这种交换（但不是同二聚体的形成）在很大程度上受到抑制。还评估了膦配体的影响。较弱的σ供体（PPh 3除外）导致更快的偶联和更高的异二聚体与同型二聚体比率，其中P（fur）3导致反应最纯净。在[Pd 2（dba）3 ]，CuI和（i-Pr）2 NH存在下，碘代炔烃2a的还原二聚作用也形成了同二聚体（与I 2 ·（i-Pr）2 NH一起）。庞大和受体取代的胺降低了2a的二聚化程度，但是最大的胺类却不能促进偶联。通过使用溴炔2b可获得更好的结果。的二聚化既不2b中，也没有H /间溴交换1和图2b，观察到。1和2b的耦合
• (Methyl Difluoroacetate)copper Reagent. Remarkable Solvent Effect on the¹⁹F-NMR Spectrum, Stability and Reactivity
  作者：Osamu Kitagawa、Takeo Taguchi、Yoshiro Kobayashi

  DOI：10.1246/cl.1989.389

  日期：1989.3

  The 19F-NMR spectrum, thermal stability and reactivity of (methyl difluoroacetate)copper reagent were found to differ remarkably depending on the solvent (DMSO, DMF, or HMPA) used. With allylic bromide or alkynyl halide a crucial solvent effect for the coupling reactions was observed.

  发现（二氟乙酸甲酯）铜试剂的 19 F-NMR 光谱、热稳定性和反应性因所使用的溶剂（DMSO、DMF 或 HMPA）而异。对于烯丙基溴或炔基卤化物，观察到偶联反应的关键溶剂效应。
• Stereoselective Synthesis of 1,4-Dienes. Application to the Preparation of Insect Pheromones (3Z,6Z)-Dodeca-3,6-dien-1-ol and (4E,7Z)-Trideca-4,7-dienyl Acetate
  作者：Michael W. Hutzinger、Allan C. Oehlschlager

  DOI：10.1021/jo00119a043

  日期：1995.7

  Stereoselective synthesis of Z,E and Z,Z-1,4-dienes has been achieved by the cross-coupling of allylic substrates with vinyl organometallic reagents. Key to this strategy was the development of a method for regiospecific incorporation of a tri-n-butylstannyl group in the gamma-position of the allylic cross-coupling partner. The steric bulk of this moiety ensures the stereochemical integrity of the allylic double bond throughout the coupling sequence and is easily replaced by hydrogen in the coupled product. This strategy has been applied to the synthesis of the termite trail marker pheromone 22 and the leafminer moth sex pheromone 28.
• Improved syntheses of methyl (14E)- and (14Z)-dehydrocrepenynate: key intermediates in plant and fungal polyacetylene biosynthesis
  作者：Lizhi Zhu、Robert E Minto

  DOI：10.1016/s0040-4039(01)00577-9

  日期：2001.6

  Efficient syntheses of the (14E)- and (14Z)-isomers of methyl dehydrocrepenynate have been achieved. The key steps involve Pd-catalyzed cross-coupling reactions furnishing the CC double bonds between C14 and C15, followed by Wittig reactions to construct the (Z)-alkene at C9. High overall yields and stereoselectivities were achieved for both isomers.

  已经实现了脱氢crepenynate的（14 E）-和（14 Z）异构体的高效合成。关键步骤包括在C14和C15之间提供C CC双键的Pd催化交叉偶联反应，然后进行Wittig反应，以在C9处构建（Z）烯烃。两种异构体均具有较高的总收率和立体选择性。